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2H+
H+
OXALOACETATE
PYRUVATE
SUCCINYL-CoA
GLUTARATE
CITRATE
MALATE
2-OXO- ASPARTATE
NO2
-
NO3
-
N2
NH4
CH3COSCoA
ACETYL-CoA
HOH
CO2
NAD
TRANSA
MINATION
2H+
2H
+
+
CO2
5-Amino-
levulinate
Glycine
H+
H+
H+
H+
H+
H+
c
H+ H+
F0
F1
F1
β2
1 α
β
α
γ
0 c-sub-units
AD
P+ Pi
3.6.1.34
H
+-transporting ATP synth
ase
α
δ
F6
oscp
ATP
ADP +Pi
FUMARATE
UQH2
UQ
UQH2
NADH+H+
CH2COO-
C(OH)COO-
CH2COO-
CH(OH)COO-
-
2COO
-
-OOCCOCH
2CH2COO
-
-OOCCH2CH2CO.SCoA
-OOCCOCH2COO-
CH3CH(OH)CH2CO.SCoA
-OOCCH=CHCOO-
Glyoxylate
Cycle
-OOCCHO
GTP
GDPATP
+
HEME Protoporphyrinogen Coproporphyrinogen Uroporphyrinogen Porphobilinogen
5-Amino-
levulinate
COO-
CH2
CH2
H2NCH2C=O
FADH2
FADCyt.b
Fe-S
SUCCINATE
II
CH3COCOO-
PYRUVATE
Pi
X Y
Cyt.c1
Fe-S
2e-
2e-
1e-
1e-
III
2UQ UQ
UQH22UQH2
2UQ.
_
UQ.
_
Cyt.bL Cyt.bH
Cyt.c
IV
CuA
CuB
CuA
1.9.3.1
2e-
Heme a
Heme a3
2H+
2H+4H+
4H+
2H+
NAD+
NADH+H+
NAD+
1.1.1.39
1.2.4.1
2.3.1.12
3.1.3.43
4.1.1.32
4.1.3.7
4.2.1.3
1.1.1.41
1.2.4.2
2.3.1.61
6.2.1.4
-OOCCH2CH2COO-
1.3.5.1
4.2.1.2
1.1.1.37
6.4.1.1
4.1.3.8
4.1.3.1
4.1.3.2
ISOCITRATE
2.6.1.1
2.3.1.16
4.1.1.71
1.2.1.16
5.1.99.1
5.4.99.2
4.3.1.1
1.4.1.2 1.4.1.14
6.3.5.4
1.6.6.1
1.7.99.4 1.7.7.1
1.6.6.4
1.1
8.6
.1
2.3.1.37
1.10.2.2
1.10.2.2
γ
εδ
β
33
β
AT
P
ADP
ENDERGONIC REACTION
1.6.5.3
I
FMNH2
FMN I
1.6. 5.3
2Fe -S
(5 Clusters)
H+ H+
H+ H+
ATP
4H+
2H+
2H+
or
H+
PHOTO-
SYSTEM
l
O2
3.6.1.34
NADP+
Glyceraldehyde
Ribulose-1,5-bis-P
2β
88
H+
c
32
ε
a
32
α1
α
ε
α
β2
1
3
α
α
β
3
α
H+
H+
H+
H+
H+H+
H+
H+
H+H+
H+H+H+H+
H+
H+
H+H+
H+
H+
H+
H+
H+
H+
H+
H+
H+
H+H+
H+H+
H+H+H+
Translocated protons
H+
H+
H+
H+
Pi
Ferredoxin
4H+
PC PC
PC
PQH2
2PQH2
PQ
_
.
2PQ
_
.
Fe-S Cyt.f
PQ
2PQ
Cyt bf
2e-
1e- 1e-
2e-
2e-
2e-
2e-
Cyclic Photophosphorylation
PQ
PHOTO-
SYSTEM
II
Cyt bc
Non-cyclic electron flo
w
2e-2e-
Mn
2e-
*
Protons from Water
H2O
H+
H+
2H+
2H+
γ
CO2
Fixation
H+
ADPPi
H+
NADPH+H+
ATPTHYLAKOID MEMBRANE
CHLOROPLAST OUTER MEMBRANE
THYLAKOID LUMEN
STROMA
(electric current)
P680
Chl.a
QA
QB
Pheophytin
P700
Chl.A0
A1
Fe-S
ATP
ADP
ATP
1/2O2
H2O
PQH2
To Brain -
A
M
I
N
O
A
C
I
D
S
P
Y
R
I
M
I
D
I
N
E
S
P
U
R
I
N
E
S
C
A
T
E
C
H
O
L
A
M
I
N
E
S
A
R
O
M
A
T
I
C
A
M
I
N
O
A
C
I
D
S
hv
VISION
L
I
P
I
D
P
H
O
T
O
S
Y
N
T
H
E
S
I
S
P
O
R
P
H
Y
R
I
N
S
S
T
E
R
O
I
D
S
I
S
O
P
R
E
N
O
I
D
S
P
H
O
S
P
H
O
L
I
P
I
D
S
D
E
G
R
A
D
A
T
I
O
N
L
I
P
I
D
B
I
O
S
Y
N
T
H
E
S
I
S
P
E
N
T
O
S
E
S
H
E
X
O
S
E
S
P
O
L
Y
S
A
C
C
H
A
R
I
D
E
S
COCH CH(NH )COO2 3
+
FOLIC
ACID
C1
POOL
VALINE
ATP
ATP
4.1.1.4 1.1.1.30
CH COCH3 3
CH COCH COO3 2
CH CH(OH)CH COO3 2
3-OH-ButyrateAcetone
Acetoacetate
KETONE BODIES
HYALURONIC ACID DERMATAN BLOOD GROUP
SUBSTANCES
PEPTIDO-
GLYCAN
N-Ac-Neuraminate
(Sialate)
UDP-
Iduronate
UDP-N-Ac-
Galactosamine
UDP-
Galacturonate
GDP-Fucose
TDP-Rhamnose
ADP-
Glucose
UDP-Glucose
TDP-4-Oxo-
6-deoxyglucose
MANNOSE
CHITIN CHONDROITIN PECTIN
ALGINATES
INULIN CELLULOSE
O-ANTIGENS STARCH GLYCOGEN
LACTOSE
GALACTOSE
O
OH
HO
OH
OH
CH3 O
OPPT
O
OH
OH
O
OH
ACNH
HO OH
O
OHHO OPPU
NHAC
OH
OH OH
OH
HO
OH
NHCOCH
OH HO
O
OPPG
CH OH2
HO
P
UDP-N-Ac-
Glucosamine
pyruvate
N-Ac-Mannosamine-6-P UDP-Glucuronate
GDP-Mannose
N-Ac-Mannosamine UDP-N-Ac-Glucosamine N-Ac-Glucosamine-6-P
Sorbitol
Fructose-1-P
Erythrose-4-P
3-Dehydrogulonate
L-Xylose
L-Lyxose
D-Xylulose
D-Ribose
Ribitol
L-Arabitol L-Xylulose
L-Ribulose L-Ribulose-5-P
L-Xylulose-5-P
L-Arabinose Xylitol D-Xylose
D-Arabinose D-Ribulose
ASCORBATE
2, 3-Dioxogulonate
N-Ac-Glucosamine-1-P
Inositol-PInositolGlucuronateGulonate
Gulonolactone 2-Oxogulonolactone
Fructose
6-P-Gluconate
D-Ribulose-5-P
D-Xylulose-5-P
Mannose-1-P
GDP-Glucose
TDP-Glucose
UDP-Galactose
Galactose-P
Glucose-1-P
Glucose-6-P
Fructose-6-P
Fructose-
1:6-bis-P
OH
H H H
O
HOCH2 C C C C CO
OH OHH OH
H H
O
HOCH2 C C C CO CO
OHH
H
OH H
C C
OH
CO
P-Ribosyl
amine
Glycerate
2, 3-Diphospho-
glycerate
3-P-Glyceraldehyde
1:3-bis-P-Glycerate
3-P-Glycerate
2-P-Glycerate
P-enolpyruvate
Inositol
CH OH2
CH OH2
HOCH
CH OH2
CH O2
HOCH
P
Glycerol
UDP-Galactose
UDP-Sugars
CH CH OH3 2
ETHANOL
Dihydroxy-
acetone-P
(Glycerone-P)
Glucosamine-6-P
Phospho-
serine
Chain elongation Mitochondrial
Serine
Serine
Indole-3-glycerol-P
3-Deoxy-D-arabino-
heptulosonate-7-P
Indoleacetate
(Auxin)
Indoxyl
Formylkynurenine Kynurenine 3-Hydroxy
kynurenine
3-Hydroxy
anthranilate
2-Amino-3-carboxy
muconate semialdehyde
NH
OH
Tryptamine 1-(o-Carboxy phenylamino)
1-deoxyribulose-5-P
N-(5-P-Ribosyl)
anthranilate
Anthranilate
Catechol
NH
Indole-
acetaldehyde
NH
CH CHO2
Indolepyruvate
N
H
C-CH(OH)CH(OH)CH O2 P
CH
2-Aminomuconate-
6-semialdehyde
CH CH NH2 2 2
NH
1.2.3.7
4.1.1.43
3.5.1.9 3.7.1.3
4.2.1.20
1.13.11.6 4.1.1.45
2.4.2.18
4.6.1.4
4.1.1.48
1.14.13.9
4.6.1.3
Dehydro-
quinate
4.2.1.10 1.1.1.25 2.5.1.19
Shikimate-3-P Shikimate-5
enolpyruvate 3-P
Chorismate
PEP
2.7.1.71
1.4
.1
.1
9
Homogentisate Phenylpyruvate
Cinnamate
Coumarate
Prephenate
2-Amino
muconate
Fumarate Aspartate
GLYCINE
Sarcosine
Hydroxy-
pyruvate
P-Hydroxy-
pyruvate
SERINE
Imidazole
glycerol-P
P-Ribosyl-ATP P-Ribosylformimino
5-aminoimidazole-
carboxamide-R P
Formimino
glutamate
Imidazolone
propionate
Urocanate
Cystathionine Homocysteine
Phosphoadenylyl-
sulphate
(PAPS)
CH (NH )COOH2 3
+
Histidinol-PHistidinolHistidinal
3.1.3.15 2.6.1.91.1.1.23
3.6.1.31
5.3.1.162.4.2.17
Asparagine
ALANINE
3-Sulphinyl
pyruvate
Oxobutyrate
2-Aceto-2-
hydroxy-
butyrate
O-Phospho-
homoserine
HO SCH CH NH2 2 2 2
Hypotaurine
HO SCH CH NH3 2 2 2
Taurine
Glutamate
γ-Glutamylcysteine
Glutathione
Glycine
Cysteine
ß-Alanine
Cysteate
S-Adenosyl
homocysteine
4.2.99.2
1.1.1.86
4.2.1.9
1.1.1.86 4.2.1.9
2.6.1.32
4.1.3.18
S-Adenosyl
methionine
(SAM)
2-Methylaceto-
acetyl-CoA
2-Acetolactate 2-3-Dihydroxy
isovalerate
2-Oxo-
isovalerate
3-Hydroxy-
isobutyrate
3-Hydroxy-
Isobutyryl-CoA
Methyl
acrylyl-CoA
2-Methyl-3-
hydroxy-
butyryl-CoA
Tiglyl-CoA 2 Methylbutyryl-
CoA
2:3-Di-OH-
3-methylvalerate
2-Oxo-3-methyl
valerate
Isobutyryl-CoA
Cysteine
sulphinate
4.2.99.9
2-Isopropyl-
malate
CH CH COCOO3 2
+
CH CH(NH )COO3 3
CH CH(OH)COO3
HO SCH COCOO2 2
OCH COCOO2P
OCH CH(NH )COO2 3P
HOCH COCOO2
HOCH CH(NH )COO2 3
+
+
OH
CH COCOO2
COO
OH
OH
O
COO
OH
OH
HO P
COO
OH
OH
O
CH2
P
COO
O-C-COO
OH
O
OH
OOC CH COCOO2
N
H
HOC-CH(OH)CH(OH)CH 2OP
CH
COO
NH2
COO
OH
NH2COO
COO
OCH
OOCCH NHCH2 3
CH (CH ) COS-ACP3 2 14 CH (CH ) COSCoA3 2 14
CH (CH ) CH=CHCO-S-ACP3 2 2
CH CH=CHCO-S-ACP3 CH CH(OH)CH COS-ACP3 2
COSCoA
Linoleate
Oleoyl-CoA
Stearoyl-CoA Dehydrostearoyl-CoA OH-Stearoyl-CoA Oxostearoyl-CoA
Palmitoyl-ACP Palmitoyl-CoA
ACYL-ACP 2, 3-Enoyl-ACP
3, 4-Decenoyl-ACP
2, 3-Decenoyl-ACP
3-OH-Acyl-ACP 3-Oxoacyl-ACP
3-Oxo-Decanoyl-ACP
3-Oxo-Hexanoyl-ACP3-OH-Hexanoyl-ACP2, 3-Hexenoyl-ACP
Butanoyl-ACP Crotonoyl-ACP 3-OH-Butanoyl-ACP Acetoacetyl-ACP
Hexanoyl-ACP
3-OH-Decanoyl-ACPDecanoyl-ACP
Palmitoleoyl-ACP
γ-Linolenate Arachidonate Leukotriene B4
COSCoA
CO-S-ACP
Thromboxane B2
HOOCCH CO-S-ACP2
Malonyl-ACP
HOOCCH CO-SCoA2
Malonyl-Co-A
CH CO-S-ACP3
Acetyl-ACP
CH O-CO-R2
CH OH2
R’-CO-OCH
FATTY ACID
ACYL-CoA
(Cytosol)
CH O-CO-R2
CH O2
R’-CO-OCH
P
Cardiolipin Phosphatidylglycerol
Acetylcholine
Glycerophosphocholine
Lysolecithin
Choline
plasmalogen
CDP-choline Choline-P
Mevaldate
CH (CH ) CH=CHCH(OH)CHCH OH3 2 12 2
Dehydrosphinganin Sphinganin 4-Sphingenin Psychosine
Acyl-CoA
Acyl-CoA
Cerebroside
GalactoseCH (CH ) CH=CHCH(OH)CHCH O-3 2 12 2
NHCOR
Isopentenyl-PP
(C5)
Dimethylallyl-PP
(C5)
Geranyl-geranyl-PP
(C20)
Farnesyl-PP
(C15)
Squalene
(C30)
Geranyl-PP
(C10)
Desmosterol Zymosterol Lanosterol
CH C = CHCH O3 2 PP
CH3
Ceramide
Gangliosides
NHCOR
CH O2 PP
OPP
CH2
CHOLESTEROL
CH C(OH)CH CH OH3 2 2
CH COO2
CH C(OH)CH CHO3 2
CH COO2
NADP+
Dehydroascorbate
OH
H O
HOCH2 C C C C CO
OHH OH
OH
H O
HOCH2 C C CO CO CO
H
NAD+
Pi
ADPADP
Phytoene
(C40)
Lycopene (C40)
ß-CAROTENE (C40)
RhodopsinMetarhodopsin
Retinoate
trans-Retinal
11-cis-Retinoltrans-Retinol
(Vitamin A)
Retinol esters
Dark
Light
Ubiquinone
(Coenzyme Q)
Menaquinone
Plastoquinone
Phylloquinone
(Vitamin K)
Opsin
CHO
CH OH2
CHO
CH OH2
CH3CH O3
CH O3 n
O
O
O
O
Phytol (C20)
α-Tocopherol
(Vitamin E)
Quinolinate
Quinolinate-
nucleotide
Nicotinate-
nucleotide
Desamino-NAD
5-Hydroxy-
tryptophan
5-Hydroxytryptamine
(SEROTONIN)
N-Acetyl-5-O-methyl-serotonin
(MELATONIN)
NH
CH CH NHCOCH2 2 3HO
NH
CH CH NHCOCH2 2 3CH O3
+
NAD( P)
NICOTINATE
N-Acetyl-serotonin
2.4.2.19
Dopamine Dopa
Dopaquinone
THYROXINEMELANIN
OH
OH
CHOHCH NHCH2 3
OH
OH
CHOHCH NH2 2
4-OH-3-Methoxy-
phenylglycol
CHOHCH NH2 2
OH
OCH3OCH3
CHOHCH OH2
OH
OCH3
4-OH-3-Methoxy-
D-mandelate
Cyclic AMP
ATP
Dephospho-Coenzyme A
4-P-Pantetheine
4-P-Pantothenylcysteine
4-P-Pantothenate
Pantoate
6.3.2.1
1.1.1.169
3.5.1.22
2.7.1.33
NH
NH
O
O
O
O
CH OH2
OH
OCH3
CH(OH)COO
H2
NH3
+
CH-COO
CO
O
COO
NRibose- P
N
+
COO
NH
CH COO2
O
OH
CH O2 P
NHCOCH NH2 2
OH
Formyl
glycinamide-R P
Urea
Formyl
glycinamidine-R P
Allantoate Allantoin URATE
ADP
Xanthine Hypoxanthine
Inosine
Adenine
Adenylo-
succinate
5-Amino
imidazole-R P
5-Amino-4-imidazole
carboxylate-R P
5-Amino-4-imidazole
(N-succinylcarboxamide)-R P
5-Aminoimidazole
carboxamide-R P
Formylamido-
imidazole-
carboxamide-R P
H NCONH2 2
HN
H C2 CHO
NH
RP
NH
C
C
C
O
C
CO
OC
NH
NH
H
N
HN
H
C
C
O
C
CH
OC
NH
N
N
HN
Carbamoyl
ß-alanine
Dihydro-
uracil Uracil
d-ADP
d-ATP
GTP GDP
XANTHOSINE-P
(XMP)
TTP
TDP
ß-Ureido
isobutyrate
Dihydro
thymine
Thymine d-UMP d-CMP d-CDP
CDP
Carbamoyl
aspartate
Dihydro
orotate
Orotate Orotidine-P Uridine-P
(UMP)
UDP
3-Amino-
isobutyrate
CH
C
NH2
CHOC
NH
NCH
C
O
CHOC
N H
HN
CH-CH3
C
O
OC
NH
HN
CH2
CH2
CH2
C
O
OC
NH
HN
C
O
CHOC
NH
HN C CH3
Methylmalonyl
semialdehyde
OHCCHCOO
CH3
CH2
C
O
CH-COOOC
NH
HN CH
C
O
C-COOOC
NH
HN
H NCONHCH CH COO2 2 2
C
C
C
CH
RP
HC
NH
NH
OOC-CH-CH COO2
N
N
N
CHO
NH
RP
NH
OC
H C2
2.7.7.43
3.1.3.29
1.1.1.158
5.1.3.13
2.7.1.38
3.2.1.23
3.1.3.29
4.1.3.20
2.7.1.60
5.1.3.14
5.1.3.7
5.1.3.1
2.7.1.4
5.4.2.3
3.1.1.17
1.1.1.49
1.1.1.21
2.7.7.23
3.1.3.251.13.99.11.1.1.19
1.1.3.8
5.3.1.3
2.7.1.53
1.1.1.9
2.7.1.15
2.7.1.17
5.1.3.4
5.1.3.1
2.2.1.2
4.1.2.13
2.7.1.11
2.7.1.47
2.2.1.1
1.2.1.12
1.1.1.29
1.1.1.95
1.3.1.35
1.14.99.25
2.3.1.41
2.3.1.41
2.3.1.41
1.1.1.100
5.3.99.5
4.2.1.60
5.3.99.3
1.14.99.1
1.13.11.34
1.3.1.10
1.3.1.9
1.14.99.5
1.3.1.9
4.2.1.61
4.2.1.60
4.2.1.60
4.2.1.59
4.2.1.58
1.3.1.9
1.3.1.9
6.2.1.3 3.1.2.20
1.1.1.100
5.3.1.1
HOOC-COOH
Oxalate
Glycolate
HOCH CHO2
Glycol
aldehyde
Ethanolamine-P
2.7.1.30
2.3.1.7
3.7.1.2
4.1.3.5
2.7.8.8
2.1.1.17
2.1.1.71
1.3.1.35 2.7.8.2
3.1.4.3
3.1.4.4
2.7.7.15
3.1.1.5 3.1.4.2
2.7.1.32
2.7.1.82
1.2.4.1
2.3.1.12
1.8.1.4
2.6.1.2
1.4.1.1
4.1.1.1
2.3.1.50
1.1.1.102
3.1.4.12
2.7.8.3
2.4.1.62
3.2.1.46
5.2.1.3
1.2.1.36
2.3.1.76
3.1.1.21
5.2.1.7
5.4.99.7
1.14.99.7
4.3.1.8
4.2.1.75
4.1.1.371.3.3.31.3.3.4
4.99.1.1
2.5.1.29
2.4.1.47
4.1.1.28 2.3.1.5 2.1.1.4
6.3.5.1
6.3.1.5
2.4.2.11
2.7.7.18
2.6.1.5
1.2.1.32
1.13.11.5
2.1.1.28
2.1.2.2 6.3.3.1
3.5.2.5
1.4.1.10
1.7.3.3 1.1.1.204 1.1.3.22
1.1.3.22
4.1.1.28
4.1.1.21
2.1.2.3
2.4.2.1
1.5.99.2
2.1.1.5
2.6.1.22
3.5.2.3
2.6.1.51
1.4.1.7
3.1.3.3
2.6.1.52
2.1.3.2
ACETATE
2.4.2.4
2.1.1.45
RP
CH
C
O
CHOC N
HN
1.3.1.14 2.4.2.10 4.1.1.23
2.7.7.7
2.7.7.7
2.7.7.7
1.17.4.1
2.7.7.7
2.7.4.14
4.4.1.1
1.6.4.1
1.13.11.20
4.4.1.8
4.2.1.22
1.1.1.27
4.1.1.29
6.3.2.3
6.3.2.2
1.8.1.3
LACTATE
Acetaldehyde
2.7.1.24
2.7.7.3
4.1.1.36
Bile Acids
CH CH COSCoA3 2
Propanoyl-CoA
1.1.1.31
2.1.3.1
4.1.1.41
5.1.99.1
6.4.1.3
6.3.2.5
2.1.1.14
2.1.1.13
4.6.1.1
CDP-Ethanolamine
1.1.1.35 4.2.1.17
+
HO SCH CH(NH )COO2 2 3
3.5.2.7
NHHN
CH
OOC CHCH CH COO2 2
CMP-N-Acetyl
neuraminate
CDP-diacyl
glycerol
CHOLINE
Ethanolamine
Glyoxylate
HISTAMINE
2.3.1.46
Homoserine
Tyramine
Plant PigmentsTannins
Maleyl
acetoacetate
Fumaryl
acetoacetate
5.2.1.2
CH COO2
OH
OH
OH
CH CH NH2 2 2
OH
OH
CH CH NH2 2 2
Hydroxyphenyl
pyruvate
α-Tocopherol
(Vitamin E)
LIGNIN
d-GTP
OH
OH OH
O
HO
OH
P
OPPT
CH3
HO
OHOH
O
NADPH
2.2.1.1
2.7.1.3
1.1.1.45
1.1.1.130
1.10.3.3
1.10.2.1
1.1.1.10
ATP
CH CH NH2 2 2
NH
HO
5.4.99.5
1.14.16.12.6.1.51.13.11.27
Indole
4.1.99.1
1.13.11.11
OH
O
OH
NH C C CH CH O2 P
H HCOO
NH2
COO
6.3.5.3 6.3.2.6 4.3.2.2
Guanine
DNA
6.3.4.44.3.2.2
C
C
O
C
CH
HC
NH
N
N
HN C
C
O
C
CH
HC
NH
N
N
HN
3.5.3.4
2.4.2.1
2.7.7.62.7.7.6
2.7.7.6
2.7.7.6
2.7.4.6
2.7.4.3
2.7.4.4
2.7.4.6
2.4.2.15
1.1.1.205
6.3.4.1
6.3.5.2
2.7.4.4
3.5.4.3
3.2.2.2
2.4.2.1
3.1.3.5
3.1.4.6
6.3.4.2
1.17.4.1
1.17.4.1
3.5.4.12
2.7.4.8
2.7.4.9
2.7.4.6
2.4.2.4
1.3.1.2
3.5.2.23.5.1.6
3.5.1.6 3.5.2.2 3.5.4.1
Diphospho-
mevalonate
Mevalonate
3-Oxopentanoyl-CoA
3-Oxoacyl-CoA3-OH-Acyl-CoA2, 3-Enoyl-CoA
2, 3-Hexenoyl-CoA 3-OH-Hexanoyl-CoA
Acetoacetyl-CoA3-OH-Butanoyl-CoACrotonoyl-CoA
Pentanoyl-CoA 3-OH-Pentanoyl-CoA
1.1.1.35
1.1.1.35
1.1.1.157
1.3.99.3
1.3.99.3
1.3.99.2
1.1.1.35
Odd C Fatty acids
Succinylhomoserine
CO2
2-OXO ACID
Glutamyl-P
Glutamine
UREA
P-CreatineCreatine Creatinine
Glycine
CITRULLINE
Glutamic
semialdehyde
2-AMINO ACID
Pyrroline-5-
carboxylate
GlyoxylatePyruvate
4-Hydroxy-
2-oxoglutarate
4-Hydroxy-
glutamate
3-Hydroxy-
pyrroline-
5-carboxylate
Putrescine
H NCH CH CH CH NH2 2 2 2 2 2
Spermidine
Spermine
N -Trimethyllysine66
N -Trimethyl-
3-OH-lysine
Carnitine
Glutaryl-CoA Saccharopine2-Aminoadipate
semialdehyde
2-Aminoadipate2-Oxoadipate
Arginino-
succinate
Guanidoacetate
Methylmalonyl-CoA
4.1.2.12
Aspartyl
Semialdehyde
2, 3-Dihydro-
dipicolinate
1.2.1.11
4.2.1.52 1.3.1.26
Piperideine-
2, 6-dicarboxylate
N-Succinyl-
2-amino-6-oxo-
pimelate
2.6.1.17
N-Succinyl-2, 6
diaminopimelate
Diamino-
pimelate
3.5.1.18
3-Methyl-
glutaconyl-CoA
(CH ) CHCH COSCoA3 2 2(CH ) CHCH COSCoA3 2 2
3-Methyl-
crotonyl-CoA
Isovaleryl-CoA
OxopantoateHCHO
OOCCH C = CHCOSCoA2
CH3
CH COCHCOSCoA3
CH3
CH CH=CHCOSCoA3
CH3
CH CH(OH)CHCOSCoA3
CH3
C(OH)CH(OH)COO
CH CH3 2
CH3
CH = CCOSCoA2
CH3
HOCH CHCOS-CoA-2
CH3
CH CHCO-SCoA3
CH3
C (OH)CH(OH)COO
CH3
CH3
CH CH CHCOSCoA3 2
CH3
CH C = CHCOSCoA3
CH3
ATP
4-Aminobutyrate
(GABA)
1.3.99.7
1.5.1.2
1.14.11.2
2.6.1.39 1.2.1.31
1.14.11.8
2.5.1.16
2.5.1.22
4.1.3.16
2.6.1.23
1.5.99.8
1.5.1.2
6.4.1.4 1.3.99.10
4.2.1.33
2.6.1.6
1.1.1.85
Oxoleucine
COOH
(CH ) CHCHCH(OH)COO3 2
S-Adenosylmethyl
thiopropylamine
(Decarboxylated SAM)
PROLINE
Coenzyme A
CH C= CHCH3 2
CH3
O
CH
CH
3
3
HO
CH3CH3
CH3
CH C-CH H O3 2 2C PP
CH2
CH C= CHCH O2 2 PP
CH3
3-P-Glycerol
Phosphatidyl
ethanolamine
CEPHALIN
3.1.4.12
2.7.8.3
Progesterone
1.5.1.12
2.7.3.2
4.2.1.173.1.2.4
2.6.1.32
4.4.1.15
Acetylserine 2.7.7.42.7.1.251.8.99.1
Adenylylsulphate
(APS)
2.7.1.39
4.4.1.15
4.1.1.29
4.2.99
.8
2.3.1.30
P-Ribosyl-PP
1.1.1.1
1.2.1.4
Aspartyl-P
5.1.1.7
2.7.1.40
4.1.3.18
4.1.3.18
1.5.1.9
1.14.11.1
CHOLINE
2.1.1.13
1.3.1.2
NHCH CH SH2 2NHCH CH CO2 2OCH C(CH ) CH(OH)CO2 3 2P
ADP- NHCH CH SH2 2NHCH CH CO2 2OCH C(CH ) CH(OH)CO2 3 2
P-ADP- NHCH CH SH2 2NHCH CH CO2 2OCH C(CH ) CH(OH)CO2 3 2
1.4.1.8
1.3.99.3
1.3.99.3
1.4.1.9
4.2.1.18
4.1.1.20
1.3.99.7
1.8.99.2
+
CH CO-OCH CH(NH )COO2 2 3
2.5.1.6
2.1.1.10
2.1.1.20
1.1.1.3
1.1.1.3
4.2.1.18
4.1.2.5
4.3.1.5
4.2.1.20
2.1.2.1
2.1
.1
.2
0
Glyoxylate
2.1.1.6
1.4.3.4
1.14.18.1
1.14.16.2
Hexanoyl-CoA
Butanoyl-CoA
6.3.4.16
6.3.5.5
2.7.2.11
2.1.3.3
NO
1.14.13.39
3.5.3.63.5.3.1
4.3.2.1
4.1.1.17
2.7.7.41
2.6.1.4
1.1.1.100
1.1.1.8
2.3.1.51
2.3.1.15
2.7.8.5
SO
-
4
2
1.14.16.4
NH2OOC
OOC
4.1.1.25
1.3.1.13
1.3.1.13
2.7.4.6
CYTIDINE-
triphosphate
(CTP)
Cytosine
2.4.2.9
4.1.1.11
2.6.1.18
4.3.1.3
4.2.1.49
3HSO-
1.1.1.105
2.3.1.41
NADPH
1.1.1.22
2.3.1.4
5.5.1.4
3.2.1.26 3.2.1.48
2.6.1.16
1.1.1.14
2.7.7.34
4.2.1.47
2.4.1.68
2.4.1.69
2.4.1.9
5.3.1.8
2.4.1.11
O
OPPU
CH OH2
CH OH2
HO OH
OH
HO
2.4.1.21
4.2
.1
.5
2
1.2.1.18
4.2.1.18
O
CH
C
CHOC
N
HN
DP
CH
C
O
CHOC
N
HN
RPPP
OCH2
H
C C
H
OHOH
CH
NHN
C
H
CP
H
O
OCH2 C C
H
OH
H
OH
C
H
C C
C
NH2
C
CH
HC
N
RP(PP)
N
N
N
+
P
NH2H
O
OCH2 C C
H
OH
H
OH
C
H
C C
OC
C
CH
HC
N
RP
N
N
NHP
H
OCH2 C C
H
OHOH
CO CH2
C
CONH2
C
CH
HC
N
RP
N
N
NHP
+
OOCCH N(CH )2 3 3
Betaine
Betaine
aldehyde
2.4.1.16
5.1.3.6
2.4.1.33
2.7.7.13
5.4.2.8
5.3.1.8
O
OH
CH OH2
HO
O PHO
2.7.1.28
2.7.1.31
6.3.4.13
5.3.1.1
2.2.1.1
4.1.1.9
3.1.2.11
ß-OH-ß-Methyl-
glutaryl-CoA
6.3.4.5
5.3.1.6
2.5.1.21
2.1.1.2
3.5.2.10
6.3.2.13
6.3.2.7-10
2.7.7.27
2.7.7.9
3.5.4.10
C
C
O
C
CH
OC
N RP
N
N
H
HN
C
C
O
C
CH
N
N
N
HN
RP
H N2 C
2.7.4.6
1.17.4.1
2.7.4.6
2.6.1.13
Carbamoyl-P
2.3.1.9
Carnitine
2.6.1.4 2.6.1.44
CH C(OH)CH COSCoA3 2
CH COO2
1.2.3.5
1.1.1.34
2.3.1.16
4.1.3.5
2.3.1.16
4.1.3.4
Menaquinone
4.1
.1
.1
5
2.6.1.19
4.2.1.16
Carnosine
CH CH NH2 2 2C
NHN
C
HC
H
4.1.1.22
4.3.1.3
Ubiquinone
Plastoquinone
D-Ribose-5-P
NH
CH CH(NH )COO2 3HO
+
O
OH
OH
HO
OPPU
COO-
O
OH
OH
HO OPPU
COO-
OH
H OH
HOCH2 C C CO
H
CO COO-
O
CHOH
CHOHAcNH
HO
OPC
OCO -
CH OH2
O
CHOH
CHOHAcNH
HO
OH
COO
CH OH2
O
OHOHHOHO
CH O2 P
O
OH
ACNH
HO OH
CH O2 P
O
OOHHOHO P
CH OH2
O
OHOH HOHO
CH OH2
O
OHHO OH
3
CH O2 P
O
OHHO O
NHCOCH3
P
CH OH2CH OH2CH OH2
O
OHHO OH
NH2
CH O2 P
O
OH
HO
OH
OPPU
CH OH2
O
O
HO
OH
OH
HO
P
CH OH2
CH OH2
O
O
HO
OH
OH
O
OHOH
OH
CH OH2
O
OHHO
OH
OH
CH2CH OP2
OH
H H HOH
C C C C
OH OHH
COO-HOCH2
H
OH OHOH
C C C CHO
HH
HOCH2
H
OH OHH
C C C CHO
HOH
HOCH2
OH
H OHH
C C C CHO
HOH
HOCH2
H
OH HOH
C C C CHO
OHH
HOCH2
OH
H HOH
C C C CHO
OHH
HOCH2
OH
H OHOH
C C C CHO
HH
HOCH2
H
OH HOH
C C C C
OHH H
OH
COO-POCH2
OH
H OH
C C CO
H
POCH2 CH OH2
H
OH H
C C CO
OH
HOCH2
CH OH2
CH OH2POCH2
H
OH OH
C C CO
H
CH OH2POCH2
OH
H H
C C CO
OH
CH OH2
POCH2
H
OH OH
C C CO
H
HOCH2
CH OH2
OH
H OH
C C CO
H
HOCH2
CH OH2
OH
H H
C C CO
OH
HOCH2 CH OH2
H
OH OHH
C C C
HOH
HOCH2 CH OH2
OH
H OHOH
C C C
HH
HOCH2
CH OH2
H
OH HOH
C C C C
OHH H
OH
CH OH2HOCH2
H
OH OH
C C CHO
H
POCH2
H
OH HOH
C C C CO
OHH
HOCH2
CH O2 P
H
OH OHOH
C C C
HH
HOCH2 CH OH2
H
OH OH
C C C
H
CO
H
HO
POCH2
CH OH2
P
H
OH OH
C C C
H
CO
H
HO
CH O2 POCH2
H
OH OH
C C
H
C CHO
OH
H
POCH2POCH2
O
OH
NH2
OH
CH O2 P
CHOHCHOPOCH2
HOCH2COCH2OP
O
OH
O OP P
OH
CH O2 P
CHOHCOOPPOCH2
CHOHPOCH2 COO
COO
OH
OHO
OH
COO
CH (CH ) CH(OH)CH COS-CoA3 2 14 2CH (CH ) CH(OH)CH COS3 2 14 2
CH (CH ) COCH COS-CoA3 2 14 2
CH (CH ) COCH COS-CoA3 2 14 2
CH (CH ) COS-CoA3 2 n+2
CH (CH ) CH=CHCOS-CoA3 2 14
CH (CH )3 2 nCH=CHCOS-CoA
CH (CH )3 2 5 2CH=CHCH COSACP
CH (CH )3 2 6CH=CHCOSACP
CH (CH )3 2 6COCH COSACP2CH (CH )3 2 6 2 2CH CH COSACP
CH (CH )3 2 2 2 2CH CH COSACP
CH CH CH COSACP3 2 2
CH (CH )3 2 6CH(OH)CH COSACP2
CH CH=CHCO.S-ACP3
CH (CH )3 2 2 2COCH COSACP
CH3COCH COSACP2
CH (CH )3 2 n 2COCH COSACPCH (CH )3 2 n 2CH(OH)CH COSACP
CH (CH )3 2 2 2CH(OH)CH COSACP
ACYL-CoA
(Mitochondria)
CH (CH ) CH CH COSCoA3 2 2 2n
CH (CH ) CH=CHCOSCoA3 2 n CH (CH CH(OH)CH COSCoA3 2n
CH (CH ) CH CH COSCoA3 2 2 2 2 CH (CH ) CH=CHCOSCoA3 2 2
CH (CH ) COCH COSCoA3 2 2n
CH COCH COSCoA3 2
CH (CH ) CH(OH)CH COSCoA3 2 2 2
CH CH(OH)CH COSCoA3 2CH CH=CHCOSCoA3CH CH CH COSCoA3 2 2
CH CH CH CH COSCoA3 2 2 2
Pentenoyl-CoA
CH CH CH=CHCOSCoA3 2 CH CH CH(OH)CH COSCoA3 2 2
CH (CH ) COCH COSCoA3 2 2 2
CH CH COCH COSCoA3 2 2
OH OH
HO OH
O
O-
CH O-PO2
CH CHOHCH OH2 2
O
CH2
CH2
R'-CO-OCH
O-CO-R
O-PO
O-
HOCH CH2 2
NH3
+POCH CH2 2NH3
+
CPP- OCH CH2 2NH3
+
O
-
CH O-CO-R2
CH O P2 OCH CH2 2NH3
+
CH COCH CH N(CH )3 2 2 3 3
HOCH CH N(CH )2 2 3 3
+
CH CH2 COO(NH )3
+
OH
OH
CH CH2 COO-(NH )3
+
CO
NH2
CH CH(NH )COO2 3
+
NH
OC
CO
NH
OC
N
H
C
H
H N2
HC
CH
N
N
C
RP
H N2
CH
C
CHOC
N
N
DP
NH2
RPPP
CH
C
CHOC
N
N
NH2
C
C
C
CH
RP(P)
HC
N
N
N
N
NH2
H NCOO2 P
(CH ) NH2 3 2H N(CH ) NH2 2 3 (CH ) NH2 4
(CH ) NH2 3 2H N(CH ) NH2 2 4
CH -SCH CH CHNH3 2 2 2
Adenosyl
+
+
CH3
CH3
CHCH(NH )COO3
++
C
NHN
C
HC
H
CH CH(NH )CH OH2 3 2
+
C
NHN
C
HC
H
CH CH(NH )CH OP2 3 2
C
NHN
C
H
HC CH COCH OP2 2
+
HSCH CH CH(NH )COO2 2 3
+
+
SCH CH CH(NH )COO2 2 3
CH CH(NH )COO2 3
RP
C
O
C-COOOC
N
HN CH
2.4.1.23
CH (CH ) CH=CHCH(OH)CHCH OH3 2 12 2
NH3
+
CH (CH ) CH(OH)CHCH OH3 2 14 2
NH3
+
CH (CH ) COCHCH OH3 2 14 2
NH3
+
GalactoseCH (CH ) CH=CHCH(OH)CHCH O-3 2 12 2
NH3
+
4.1.1.70
H NCONH2 2
OHCCH N(CH )2 3 3
+
C-CH3
C
O
CHOC
N
DP
HN
DP
CPP-OCH CH N(CH )2 2 3 3
+
OCH CH N(CH )2 2 3 3
+
1.2.1.41
UDP-N-Ac-Muramate
O
O
CH CH3
COO-
NHAC
HO OPPU
CH OH2
4.1.3.20
O
OH
CH3
HO HO OPPG
2.7.7.24
2.4.1.22
2.7.7.12
5.1.3.2
5.3.1.4
Sedoheptulose-PP
3.1.1.28
4.2.1.24
N
CH2
CH2
N
N
N
CH3
CH3
CH
CH
COO
CH
CH
CH2
H C3
H C3H C3
HC
C
C
H
H
Fe
CH2
CH2
COO- -
CH3
CH3
CH2
CH2
CH2
H C3
H C3
N
H
N
H
N
H
N
H
CH
CH
H C2
C
C
H2
H2
-
CH2
CH2
COO
CH2
CH2
COO -
H C2
H C2
CH 2
CH 2
OOC
COO
H N2
N
H
-
-
CH2
H C2
H C2
H C2
H2
H2
CH2
CH2 CH2
CH2
CH2
CH2
N
H
N
H
N
H
N
H
COO
COO
COO
COO
C
C
-
-
CH2
CH2
COO
CH2
CH2
COO- -
-
-
OOC-
OOC
-
CH3
CH3
H C3
H C3
H C2
H2
H2
N
H
N
H
N
H
N
H
CH2
CH2
CH2
CH2
CH2
C
C
COO-
CH2
CH2
COO
CH2
CH2
COO- -
COO-
COO-
CH C(OH)CH CH O3 2 2 PP
CH COO2
OHCCOO
HOCH COO2
NH2
H NCNHCH COO2 2
+ NH2
H NCN(CH )CH COO2 3 2
+ NH2
HNCN(CH )CH COO3 2P-
+ HN C
NH CO
N CH2
CH3
OOCCHCH COO2
H NCNHCH CH CH CH2 2 2 2
N
(NH )3
+
COO
CHCOOHC
CH2HOCH
N
OOCCH(OH)CH CH(NH )COO2 3
+
CHCOO
CH2HOCH
H C2
N
H
NH
CHCOO
CH2CH2
CH2
OOCCH(OH)CH COCOO2
N
CHCOO
CH2CH2
CH
CH COCOO3 OHCCOO
+
H NCONHCH CH CH CH2 2 2 2 (NH )3
COO
H NOCCH CH CH2 2 2 COO(NH )3
+
R-CO-COO
+
COOR-CH(NH )3
+
COOH NOCCH CH2 2 (NH3
+
OOC-CH-COSCoA
CH3
P OOCCH CH2 COO(NH )3
+
OOCCH CH CHO2 2
OHCCH CH2 COO(NH )3
+
(CH ) NCH CH(OH)CH COO3 3 2 2
+
OHCCH CH CH2 2
+
COO(NH )3
POOCCH CH CH2 2
+
COO(NH )3
OHCCH CH CH CH2 2 2 COO(NH )3
+
NH CHCH CH COO2 2
COO
CH CH CH CH CH2 2 2 2 COO(NH )3
+
H N(CH )2 42 CH(NH )COO3CH(NH3
++
(CH ) N(CH )3 3 2 3CH CH(NH )COO2 3
+ +
CH2
C
H
OOCC
N
HC
CH-COO
CH2
C
H2
CH-COOOOCC
N
H C2
OOCCOCH CH CH CH-COO2 2 2CH CH2 2 2
OOCCH CH CONH2 2 OOCCHCH CH CH CH-COO2 2 2
OOCCH CH CONH2 2CH2 2
NH3
+
OOCCH-CH CH CH CHCOO2 2 2
NH3
+
NH3
+
(CH ) CHC(OH)CH3 2 2
COOH
COO (CH ) CHCH COCOO3 2 2
+
(CH ) CHCH3 2 2
CH(NH )COO3
HOCH CHCOO2
CH3
CHCOCOO
CH3
CH3CH COC(OH)CH3 3
COO
+
POCH CH CH(NH )COO2 2 3
+
HOCH CH CH(NH )COO2 2 3
+
CH CH CH(NH )COO2 2 3OOCCH CH2COO2
+
CH SH2
OOCCH(NH )CH CH CONHCHCONHCH COO3 2 2 2
HOCH C(CH ) COCOO2 3 2
HOCH C(CH ) CH(OH)COO2 3 2
NHCH CH COO2 2HOCH C(CH ) CH(OH)CO3 2)2 3 2
NHCH CH COO2 2OCH C(CH ) CH(OH)CO2 3 2P
CH CH3 2
CH3
CH
+
CH(NH )COO3
CH COC(OH)CH CH3 2 3
COO CHCOCOO
CH CH3 2
CH3
NHCHCH SH2
COO
NHCH CH CO2 2OCH C(CH ) CH(OH)CO2 3 2P
+
CH SH2
OOCCH(NH )CH CH CONHCHCOO3 2 2
+
Adenosyl
SCH CH CH(NH )COO2 2 3
+
SCH CH CH(NH )COO2 2 3
+
HO SCH CH(NH )COO3 2 3
+
+
S-CH CH(NH )COO2 3
S-CH CH(NH )COO2 3
+
HSCH CH(NH )COO2 3
1.1.1.23
H
C
NHN
C
HC CH CHCOO2
NHCOCH CH NH2 2 2
+
H
C
NHN
C
HC CH CH(NH )COO2 3
CHCH CH COO2 2
NHN
CH
OC C CH CHCOO
NHN
CH
CH
CH COO3
N
H
OOC
CH-COOOC
NH2 CH2
H NCH CH COO2 2 2
H NCH2 2
CH3
CHCOO H NCONHCH CHCOO2 2
CH3
C
C
O
CH
RP
HC
N
N
N
HN
C
CC
O
CH
HCO
N
N
N RP
C
CH
N
N
H N2
H
C
C
C
O
CH
N
N
C
C
CH
N
N
RP
H N2
H N2
C
O
O
O P~ ~P O
O
O O
P O
O
CH2
N
N
N
N
O
OHOH
NH2
HC
CH
N
N
N
N
O
O
P O O
O
CH2
OH
NH2
HC
CH
COO
CO
NH
OC
N
H
C
H
H N2
NH2
OOC-CH-CH COO2
HNCO C
CH
N
N
C
RPRP
H N2
OOC
C
CH
N
RP
N
C
H N2
CH=CHCOO
OH
CH=CHCOO
CH COCOO2
CH2
P
COO
OH
O
O
O
COO
O
CH COO2
O
CH COO2-OOC
OCH2 CH2
OHH
C
P
HOCH HCOH
OC
COO
COOHO
OH
OHO
NH2
COO
OCH
NH
CH COCOO2
NH
CHO
CO
NH2
OH
CH CH(NH )COO2 3
+
N
COO
COO
N
+
COO
COO
RP
O
OH
OH
HO OPPU
COO
O
OH
NHCOCH3
HO
OPPU
COO
CH OH2
O
O
CCH2 NHAC
HO OPPU
COO
CH OH2
O
OHHO OH
OH
COO
OOCCH N(CH )2 3 2
Dimethylglycine
1.1.99.1
1.2.1.8
COO
HO HO
COO
O
HO OH
COO
CH(O )PPOCH2 COO
CH(OH)HOCH2 COOCOO
CH(O )PHOCH2 COO
CH =C(O )2 P COO
CONH2
Ribose -O - P - O - P - O- Adenosine(P)
+
N
O
O
O
O
+
COO
N
Ribose - O - P - O - P - O -Adenosine
O
O
O
O
II
II
OH
O
CH CH2 COO(NH )3
+
Epinephrine
(Adrenaline)
Norepinephrine
(Noradrenaline)
Normetepinephrine
(Normetadrenaline)
HOCH CH N(CH )2 2 3 3
+
Adenosyl
+
+
SCH CH CH(NH )COO2 2 3
CH3
(CH ) N(CH )3 3 2 3CH CH(NH )COO2 3
+ +
OH
OOCCH CH CH COSCoA2 2 2
OOCCH CH CH NH2 2 2 2
OOCCH CH CH COCOO2 2 2 OOCCH CH CH CH2 2 2 COOCOO(NH )3
++
HO
H
HO
H
H
HO
H
HO
H
Prostaglandin PGE 2
OH
HOCH2 C C CO C COO
OHH
OHH H
-
COO
OR'-CO-OCH
CH O-CO-R2
CH O POCMP2
O
CH CH N(CH )2 2 3
+
OHOCH
CH OPO2
CH OH2
O-
CH OPO2
O
CH OCH=CHR2
CH CH N(CH )2 2 3 3
+
O-
CH OPO2
OR'-CO-OCH
CH O-CO-R2
3.1.1.32
CH CH N(CH )2 2 3 3
+
O-
OHOCH
CH OPO2
CH O-CO-R2
CH CH N(CH )2 2 3 3
+
O-
CH CH(NH )COO2 3
+
+
C
NHN
C
HC
H
CH CH(NH )CHO2 3
HS
11-cis-Retinal
Pi
ADP
NADP+
GDP-
Mannuronate
Mannose-6-P
Dehydro-
shikimate
Shikimate
RNA
d-GDP
d-CTP
GUANOSINE-P
(GMP)
ß-Alanine
P-Ribosyl-AMP P-Ribulosylformimino
5-aminoimidazole-
carboxamide-R P
Imidazole
acetol-P
HS HSO-
PANTOTHENATE
3-Isopropyl-
malate
Succinic
semialdehyde
2.4.1.17
Diacyl
glycerol
2.3.1.6
1.14.12.1
1.4.4.2
CH CHO3
3.5.4.19
4.2.1.19
3.3.1.1
4.1.1.12
4.1.2.5
COO-2OHCCH
2.1.4.1
2.4.99.7
5.1.3.12
1.1.1.132
4.2.1.46
2.7.1.7
2.4.1.29
2.4.1.21
2.4.1.13
2.4.1.1
etc.
5.4.2.2
2.7.1.6
2.7.7.10
3.1.1.18
4.1.1.34
2.7.1.47
2.7.1.16
3.1.3.9
ADP
P-Glucono
lactone
1.1.1.44
O
O
OHHO
OH
CH O2 P
PHENYLALANINETYROSINE
TRYPTOPHAN
INOSINE-P
(IMP)
THYMIDINE-P
HISTIDINE
URIDINE-
triphosphate
(UTP)
CYSTINE CYSTEINE
ISOLEUCINE
LEUCINE
LYSINE
ORNITHINE
ARGININE
HYDROXY
PROLINE
PHOSPHATIDYL
SERINEPhosphatidyl
inositol
LECITHIN
SPHINGOMYELIN
STEROIDS
Pregnenolone
2.7.6.1
2.4.2.14
6.3.4.7
5.3.1.9
3.1.3.11
1.2.1.13
2.7.2.3
H
OH OH
C C C
H
CO
OH
C
H
H
OH
POCH2
CH O2 P
5.4.2.1
ADP
4.2.1.11
Endoplasmic Reticulum
1.1.1.100
3.1.1.3
Phosphatidate
2.3.1.39
4.2.1.17
4.2.1.17
4.2.1.55
1.1.1.79
1.2.1.21
1.4.3.8
1.1.1.32
2.7.1.36
2.7.4.2
4.1.1.33
2.5.1.1
2.5.1.10
2.7.8.5
2.7.8.1
4.1.1.65
2.7.7.14
1.3.99.7
PO
O
CH (CH ) CH=CHCH(OH)CHCH O3 2 12 2
NHAcyl
CH CH N(CH )2 2 3 3
+
O-
3.5.1.23
1.13.11.21
2.5.1.32
1.1.1.105
2.4.2.19
1.2.1.32
METHIONINE
4.1.3.27
4.2.1.51
1.14.17.1
1.14.18.1
1.14.13.11
Glycinamide-
ribosyl-P
4.2.1.22
3-Oxohexanoyl-CoA
THREONINE
1.2.1.25
1.2.1.25
1.2.1.25
1.5.1.7 - 10
GLUTAMATE
2.3.1.38
ATP
NADH
SUCROSE
ADENOSINE-P
(AMP)
Triacylglycerol
FAT
RNA
CH3
CH2
OC-COOOH
COO
CH CH2 COO(NH )3
+
GLYCOPROTEINS
GANGLIOSIDES
MUCINS
4.1.2.-
2.6.1.-
GLUCOSE
O-Acyl-carnitine
O-Acyl-carnitine
OH
O-
-
R-CO-OCH
R'-CO-OCH
R'-CO-OCH
O HCO-CO-R
CH CH(OH)CH O-P-OCH2 2 2
CH O-CO-R’2
OR'-CO-OCH
O-
CH O-CO-R2
CH O-PO2
O-
2.7.8.11
H NCH CH CH CH2 2 2 2 COO(NH )3
+
2.3.1.20 3.1.3.4 2.7.1.107
NH2
+
+
H NCNHCH CH CH CH2 2 2 2 COO(NH )3
H
OH HOH
C C C CO
OHH
HOCH2
CH OH2
R-CH2COO
CH O-CO-R2
CH O-CO-R"2
R’-CO-OCH
OH
O
CH CHNH2 3
+
OR'-CO-OCH
O-
CH O-CO-R2
CH O PO2
COO
OOCCH CH CH2 2
COO(NH )3
+
CH CH(OH)CH(NH )COO3 3
O
OHHO
OH
OH
CH OH2CH OH2
NH
CH O-CO-R2
1.3.1.13
4.1.1.28
Malonic
semi-
aldehyde
2.7.2.4
2.1.3.3
3.5.1.2
6.3.1.2
6.3
.5
.5
Carbohydrates
Biosynthesis
Degradation
Amino Acids
Biosynthesis
Degradation
Lipids
Biosynthesis
Degradation
Purines &
Pyrimidines
Biosynthesis
Degradation
Biosynthesis Degradation
Vitamins Co-enzymes & Hormones
Pentose Phosphate Pathway
Photosynthesis Dark Reactions
COMPARTMENTATION
The "Backbone" of metabolism involves
GLYCOLYSIS in the CYTOPLASM,
the TCA CYCLE (mainly) in the Mitochondrial matrix
and ATP FORMATION spanning the
MITOCHONDRIAL INNER MEMBRANE
An electron flow (an electric current) generated from
NADH and UQH2 drives the translocation of protons
from the matrix to the intermembrane space.
The retrolocation of these protons through the F0 subunits
of ATP synthase to the matrix then supplies the energy
needed to form ATP from ADP and phosphate
Electron Flow Proton Flow
Small Numbers ( eg. 2.4.6.7) refer to the IUBMBEnzyme
Commission (EC) Reference Numbers of Enzymes
LEGEND
Human Metabolism is identified as far possible by black arrows
Biosynthesis Degradation
HEMOGLOBIN CHLOROPHYLL
ATP
TRANSLOC
ATED PROTONS
2.7.1.1
ATP
2.7.1.2
Metabolic PathwaysMetabolic Pathways
Argentina
SIGMA-ALDRICH DE
ARGENTINA, S.A.
Tel: 54 11 4556 1472
Fax: 54 11 4552 1698
Australia
SIGMA-ALDRICH PTY., LIMITED
Free Tel: 1800 800 097
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SIGMA-ALDRICH NV/SA.
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SIGMA-ALDRICH s.r.o.
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Tel: 43 56 59 10
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SIGMA-ALDRICH CHEMIE GmbH
Free Tel: 0800-51 55 000
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Greece
SIGMA-ALDRICH (O.M.) LTD
Tel: 30 210 9948010
Fax: 30 210 9943831
Hungary
SIGMA-ALDRICH Kft
Tel: 06-1-235-9054
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Ingyenes zöld telefon: 06-80-355-355
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India
SIGMA-ALDRICH CHEMICALS
PRIVATE LIMITED
Telephone
Bangalore: 91-80-5112-7272
Hyderabad:
91-40-5531 5548 / 2784 2378
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91-22-2579 7588 / 2570 2364
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91-11-2616 5477 / 2619 5360
Fax
Bangalore: 91-80-5112-7473
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New Delhi: 91-11-2616 5611
Ireland
SIGMA-ALDRICH IRELAND LTD.
Free Tel: 1800 200 888
Free Fax: 1800 600 222
Israel
SIGMA-ALDRICH ISRAEL LTD.
Tel: 08-948-4100
Fax: 08-948-4200
Italy
SIGMA-ALDRICH S.r.l.
Telefono: 02 33417310
Fax: 02 38010737
Numero Verde: 800-827018
Japan
SIGMA-ALDRICH JAPAN K.K.
Tokyo Tel: 03 5821 3111
Tokyo Fax: 03 5821 3170
Korea
SIGMA-ALDRICH KOREA
Tel: 031-329-9000
Fax: 031-329-9090
Malaysia
SIGMA-ALDRICH (M) SDN. BHD
Tel: 603-56353321
Fax: 603-56354116
Mexico
SIGMA-ALDRICH QUÍMICA,
S.A. de C.V.
Free Tel: 01-800-007-5300
Free Fax: 01-800-712-9920
The Netherlands
SIGMA-ALDRICH CHEMIE BV
Tel Gratis: 0800-0229088
Fax Gratis: 0800-0229089
Tel: 078-6205411
Fax: 078-6205421
New Zealand
SIGMA-ALDRICH PTY., LIMITED
Free Tel: 0800 936 666
Free Fax: 0800 937 777
Norway
SIGMA-ALDRICH NORWAY AS
Tel: 23 17 60 60
Fax: 23 17 60 50
Poland
SIGMA-ALDRICH Sp. z o.o.
Tel: (+61) 829 01 00
Fax: (+61) 829 01 20
Portugal
SIGMA-ALDRICH QUÍMICA, S.A.
Free Tel: 800 20 21 80
Free Fax: 800 20 21 78
Russia
SIGMA-ALDRICH RUSSIA
TechCare Systems, Inc.
(SAF-LAB)
Tel: 095-975-1917/3321
Fax: 095-975-4792
Singapore
SIGMA-ALDRICH PTE. LTD.
Tel: 65-6271 1089
Fax: 65-6271 1571
South Africa
SIGMA-ALDRICH
SOUTH AFRICA (PTY) LTD.
Tel: 27 11 979 1188
Fax: 27 11 979 1119
Spain
SIGMA-ALDRICH QUÍMICA S.A.
Free Tel: 900101376
Free Fax: 900102028
Sweden
SIGMA-ALDRICH SWEDEN AB
Tel: 020-350510
Fax: 020-352522
Outside Sweden Tel: +46 8 7424200
Outside Sweden Fax: +46 8 7424243
Switzerland
FLUKA CHEMIE GmbH
Swiss Free Call: 0800 80 00 80
Tel: +41 81 755 2828
Fax: +41 81 755 2815
United Kingdom
SIGMA-ALDRICH COMPANY LTD.
Free Tel: 0800 717181
Free Fax: 0800 378785
Tel: 01747 833000
Fax: 01747 833313
United States
SIGMA-ALDRICH
P.O. Box 14508
St. Louis, Missouri 63178
Toll-free: 800-325-3010
Call Collect: 314-771-5750
Toll-Free Fax: 800-325-5052
Tel: 314-771-5765
Fax: 314-771-5757
Internet:
sigma-aldrich.com
©2003 International Union of Biochemistry and Molecular Biology
www.iubmb.org
22nd
Edition Designed by Donald E. Nicholson, D.Sc., The University of Leeds, England – and Sigma-Aldrich
Product No. M 3907
XXX

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Mapa metabólico

  • 1. sigma-aldrich.com/pathways 2H+ H+ OXALOACETATE PYRUVATE SUCCINYL-CoA GLUTARATE CITRATE MALATE 2-OXO- ASPARTATE NO2 - NO3 - N2 NH4 CH3COSCoA ACETYL-CoA HOH CO2 NAD TRANSA MINATION 2H+ 2H + + CO2 5-Amino- levulinate Glycine H+ H+ H+ H+ H+ H+ c H+ H+ F0 F1 F1 β2 1 α β α γ 0 c-sub-units AD P+ Pi 3.6.1.34 H +-transporting ATP synth ase α δ F6 oscp ATP ADP +Pi FUMARATE UQH2 UQ UQH2 NADH+H+ CH2COO- C(OH)COO- CH2COO- CH(OH)COO- - 2COO - -OOCCOCH 2CH2COO - -OOCCH2CH2CO.SCoA -OOCCOCH2COO- CH3CH(OH)CH2CO.SCoA -OOCCH=CHCOO- Glyoxylate Cycle -OOCCHO GTP GDPATP + HEME Protoporphyrinogen Coproporphyrinogen Uroporphyrinogen Porphobilinogen 5-Amino- levulinate COO- CH2 CH2 H2NCH2C=O FADH2 FADCyt.b Fe-S SUCCINATE II CH3COCOO- PYRUVATE Pi X Y Cyt.c1 Fe-S 2e- 2e- 1e- 1e- III 2UQ UQ UQH22UQH2 2UQ. _ UQ. _ Cyt.bL Cyt.bH Cyt.c IV CuA CuB CuA 1.9.3.1 2e- Heme a Heme a3 2H+ 2H+4H+ 4H+ 2H+ NAD+ NADH+H+ NAD+ 1.1.1.39 1.2.4.1 2.3.1.12 3.1.3.43 4.1.1.32 4.1.3.7 4.2.1.3 1.1.1.41 1.2.4.2 2.3.1.61 6.2.1.4 -OOCCH2CH2COO- 1.3.5.1 4.2.1.2 1.1.1.37 6.4.1.1 4.1.3.8 4.1.3.1 4.1.3.2 ISOCITRATE 2.6.1.1 2.3.1.16 4.1.1.71 1.2.1.16 5.1.99.1 5.4.99.2 4.3.1.1 1.4.1.2 1.4.1.14 6.3.5.4 1.6.6.1 1.7.99.4 1.7.7.1 1.6.6.4 1.1 8.6 .1 2.3.1.37 1.10.2.2 1.10.2.2 γ εδ β 33 β AT P ADP ENDERGONIC REACTION 1.6.5.3 I FMNH2 FMN I 1.6. 5.3 2Fe -S (5 Clusters) H+ H+ H+ H+ ATP 4H+ 2H+ 2H+ or H+ PHOTO- SYSTEM l O2 3.6.1.34 NADP+ Glyceraldehyde Ribulose-1,5-bis-P 2β 88 H+ c 32 ε a 32 α1 α ε α β2 1 3 α α β 3 α H+ H+ H+ H+ H+H+ H+ H+ H+H+ H+H+H+H+ H+ H+ H+H+ H+ H+ H+ H+ H+ H+ H+ H+ H+ H+H+ H+H+ H+H+H+ Translocated protons H+ H+ H+ H+ Pi Ferredoxin 4H+ PC PC PC PQH2 2PQH2 PQ _ . 2PQ _ . Fe-S Cyt.f PQ 2PQ Cyt bf 2e- 1e- 1e- 2e- 2e- 2e- 2e- Cyclic Photophosphorylation PQ PHOTO- SYSTEM II Cyt bc Non-cyclic electron flo w 2e-2e- Mn 2e- * Protons from Water H2O H+ H+ 2H+ 2H+ γ CO2 Fixation H+ ADPPi H+ NADPH+H+ ATPTHYLAKOID MEMBRANE CHLOROPLAST OUTER MEMBRANE THYLAKOID LUMEN STROMA (electric current) P680 Chl.a QA QB Pheophytin P700 Chl.A0 A1 Fe-S ATP ADP ATP 1/2O2 H2O PQH2 To Brain - A M I N O A C I D S P Y R I M I D I N E S P U R I N E S C A T E C H O L A M I N E S A R O M A T I C A M I N O A C I D S hv VISION L I P I D P H O T O S Y N T H E S I S P O R P H Y R I N S S T E R O I D S I S O P R E N O I D S P H O S P H O L I P I D S D E G R A D A T I O N L I P I D B I O S Y N T H E S I S P E N T O S E S H E X O S E S P O L Y S A C C H A R I D E S COCH CH(NH )COO2 3 + FOLIC ACID C1 POOL VALINE ATP ATP 4.1.1.4 1.1.1.30 CH COCH3 3 CH COCH COO3 2 CH CH(OH)CH COO3 2 3-OH-ButyrateAcetone Acetoacetate KETONE BODIES HYALURONIC ACID DERMATAN BLOOD GROUP SUBSTANCES PEPTIDO- GLYCAN N-Ac-Neuraminate (Sialate) UDP- Iduronate UDP-N-Ac- Galactosamine UDP- Galacturonate GDP-Fucose TDP-Rhamnose ADP- Glucose UDP-Glucose TDP-4-Oxo- 6-deoxyglucose MANNOSE CHITIN CHONDROITIN PECTIN ALGINATES INULIN CELLULOSE O-ANTIGENS STARCH GLYCOGEN LACTOSE GALACTOSE O OH HO OH OH CH3 O OPPT O OH OH O OH ACNH HO OH O OHHO OPPU NHAC OH OH OH OH HO OH NHCOCH OH HO O OPPG CH OH2 HO P UDP-N-Ac- Glucosamine pyruvate N-Ac-Mannosamine-6-P UDP-Glucuronate GDP-Mannose N-Ac-Mannosamine UDP-N-Ac-Glucosamine N-Ac-Glucosamine-6-P Sorbitol Fructose-1-P Erythrose-4-P 3-Dehydrogulonate L-Xylose L-Lyxose D-Xylulose D-Ribose Ribitol L-Arabitol L-Xylulose L-Ribulose L-Ribulose-5-P L-Xylulose-5-P L-Arabinose Xylitol D-Xylose D-Arabinose D-Ribulose ASCORBATE 2, 3-Dioxogulonate N-Ac-Glucosamine-1-P Inositol-PInositolGlucuronateGulonate Gulonolactone 2-Oxogulonolactone Fructose 6-P-Gluconate D-Ribulose-5-P D-Xylulose-5-P Mannose-1-P GDP-Glucose TDP-Glucose UDP-Galactose Galactose-P Glucose-1-P Glucose-6-P Fructose-6-P Fructose- 1:6-bis-P OH H H H O HOCH2 C C C C CO OH OHH OH H H O HOCH2 C C C CO CO OHH H OH H C C OH CO P-Ribosyl amine Glycerate 2, 3-Diphospho- glycerate 3-P-Glyceraldehyde 1:3-bis-P-Glycerate 3-P-Glycerate 2-P-Glycerate P-enolpyruvate Inositol CH OH2 CH OH2 HOCH CH OH2 CH O2 HOCH P Glycerol UDP-Galactose UDP-Sugars CH CH OH3 2 ETHANOL Dihydroxy- acetone-P (Glycerone-P) Glucosamine-6-P Phospho- serine Chain elongation Mitochondrial Serine Serine Indole-3-glycerol-P 3-Deoxy-D-arabino- heptulosonate-7-P Indoleacetate (Auxin) Indoxyl Formylkynurenine Kynurenine 3-Hydroxy kynurenine 3-Hydroxy anthranilate 2-Amino-3-carboxy muconate semialdehyde NH OH Tryptamine 1-(o-Carboxy phenylamino) 1-deoxyribulose-5-P N-(5-P-Ribosyl) anthranilate Anthranilate Catechol NH Indole- acetaldehyde NH CH CHO2 Indolepyruvate N H C-CH(OH)CH(OH)CH O2 P CH 2-Aminomuconate- 6-semialdehyde CH CH NH2 2 2 NH 1.2.3.7 4.1.1.43 3.5.1.9 3.7.1.3 4.2.1.20 1.13.11.6 4.1.1.45 2.4.2.18 4.6.1.4 4.1.1.48 1.14.13.9 4.6.1.3 Dehydro- quinate 4.2.1.10 1.1.1.25 2.5.1.19 Shikimate-3-P Shikimate-5 enolpyruvate 3-P Chorismate PEP 2.7.1.71 1.4 .1 .1 9 Homogentisate Phenylpyruvate Cinnamate Coumarate Prephenate 2-Amino muconate Fumarate Aspartate GLYCINE Sarcosine Hydroxy- pyruvate P-Hydroxy- pyruvate SERINE Imidazole glycerol-P P-Ribosyl-ATP P-Ribosylformimino 5-aminoimidazole- carboxamide-R P Formimino glutamate Imidazolone propionate Urocanate Cystathionine Homocysteine Phosphoadenylyl- sulphate (PAPS) CH (NH )COOH2 3 + Histidinol-PHistidinolHistidinal 3.1.3.15 2.6.1.91.1.1.23 3.6.1.31 5.3.1.162.4.2.17 Asparagine ALANINE 3-Sulphinyl pyruvate Oxobutyrate 2-Aceto-2- hydroxy- butyrate O-Phospho- homoserine HO SCH CH NH2 2 2 2 Hypotaurine HO SCH CH NH3 2 2 2 Taurine Glutamate γ-Glutamylcysteine Glutathione Glycine Cysteine ß-Alanine Cysteate S-Adenosyl homocysteine 4.2.99.2 1.1.1.86 4.2.1.9 1.1.1.86 4.2.1.9 2.6.1.32 4.1.3.18 S-Adenosyl methionine (SAM) 2-Methylaceto- acetyl-CoA 2-Acetolactate 2-3-Dihydroxy isovalerate 2-Oxo- isovalerate 3-Hydroxy- isobutyrate 3-Hydroxy- Isobutyryl-CoA Methyl acrylyl-CoA 2-Methyl-3- hydroxy- butyryl-CoA Tiglyl-CoA 2 Methylbutyryl- CoA 2:3-Di-OH- 3-methylvalerate 2-Oxo-3-methyl valerate Isobutyryl-CoA Cysteine sulphinate 4.2.99.9 2-Isopropyl- malate CH CH COCOO3 2 + CH CH(NH )COO3 3 CH CH(OH)COO3 HO SCH COCOO2 2 OCH COCOO2P OCH CH(NH )COO2 3P HOCH COCOO2 HOCH CH(NH )COO2 3 + + OH CH COCOO2 COO OH OH O COO OH OH HO P COO OH OH O CH2 P COO O-C-COO OH O OH OOC CH COCOO2 N H HOC-CH(OH)CH(OH)CH 2OP CH COO NH2 COO OH NH2COO COO OCH OOCCH NHCH2 3 CH (CH ) COS-ACP3 2 14 CH (CH ) COSCoA3 2 14 CH (CH ) CH=CHCO-S-ACP3 2 2 CH CH=CHCO-S-ACP3 CH CH(OH)CH COS-ACP3 2 COSCoA Linoleate Oleoyl-CoA Stearoyl-CoA Dehydrostearoyl-CoA OH-Stearoyl-CoA Oxostearoyl-CoA Palmitoyl-ACP Palmitoyl-CoA ACYL-ACP 2, 3-Enoyl-ACP 3, 4-Decenoyl-ACP 2, 3-Decenoyl-ACP 3-OH-Acyl-ACP 3-Oxoacyl-ACP 3-Oxo-Decanoyl-ACP 3-Oxo-Hexanoyl-ACP3-OH-Hexanoyl-ACP2, 3-Hexenoyl-ACP Butanoyl-ACP Crotonoyl-ACP 3-OH-Butanoyl-ACP Acetoacetyl-ACP Hexanoyl-ACP 3-OH-Decanoyl-ACPDecanoyl-ACP Palmitoleoyl-ACP γ-Linolenate Arachidonate Leukotriene B4 COSCoA CO-S-ACP Thromboxane B2 HOOCCH CO-S-ACP2 Malonyl-ACP HOOCCH CO-SCoA2 Malonyl-Co-A CH CO-S-ACP3 Acetyl-ACP CH O-CO-R2 CH OH2 R’-CO-OCH FATTY ACID ACYL-CoA (Cytosol) CH O-CO-R2 CH O2 R’-CO-OCH P Cardiolipin Phosphatidylglycerol Acetylcholine Glycerophosphocholine Lysolecithin Choline plasmalogen CDP-choline Choline-P Mevaldate CH (CH ) CH=CHCH(OH)CHCH OH3 2 12 2 Dehydrosphinganin Sphinganin 4-Sphingenin Psychosine Acyl-CoA Acyl-CoA Cerebroside GalactoseCH (CH ) CH=CHCH(OH)CHCH O-3 2 12 2 NHCOR Isopentenyl-PP (C5) Dimethylallyl-PP (C5) Geranyl-geranyl-PP (C20) Farnesyl-PP (C15) Squalene (C30) Geranyl-PP (C10) Desmosterol Zymosterol Lanosterol CH C = CHCH O3 2 PP CH3 Ceramide Gangliosides NHCOR CH O2 PP OPP CH2 CHOLESTEROL CH C(OH)CH CH OH3 2 2 CH COO2 CH C(OH)CH CHO3 2 CH COO2 NADP+ Dehydroascorbate OH H O HOCH2 C C C C CO OHH OH OH H O HOCH2 C C CO CO CO H NAD+ Pi ADPADP Phytoene (C40) Lycopene (C40) ß-CAROTENE (C40) RhodopsinMetarhodopsin Retinoate trans-Retinal 11-cis-Retinoltrans-Retinol (Vitamin A) Retinol esters Dark Light Ubiquinone (Coenzyme Q) Menaquinone Plastoquinone Phylloquinone (Vitamin K) Opsin CHO CH OH2 CHO CH OH2 CH3CH O3 CH O3 n O O O O Phytol (C20) α-Tocopherol (Vitamin E) Quinolinate Quinolinate- nucleotide Nicotinate- nucleotide Desamino-NAD 5-Hydroxy- tryptophan 5-Hydroxytryptamine (SEROTONIN) N-Acetyl-5-O-methyl-serotonin (MELATONIN) NH CH CH NHCOCH2 2 3HO NH CH CH NHCOCH2 2 3CH O3 + NAD( P) NICOTINATE N-Acetyl-serotonin 2.4.2.19 Dopamine Dopa Dopaquinone THYROXINEMELANIN OH OH CHOHCH NHCH2 3 OH OH CHOHCH NH2 2 4-OH-3-Methoxy- phenylglycol CHOHCH NH2 2 OH OCH3OCH3 CHOHCH OH2 OH OCH3 4-OH-3-Methoxy- D-mandelate Cyclic AMP ATP Dephospho-Coenzyme A 4-P-Pantetheine 4-P-Pantothenylcysteine 4-P-Pantothenate Pantoate 6.3.2.1 1.1.1.169 3.5.1.22 2.7.1.33 NH NH O O O O CH OH2 OH OCH3 CH(OH)COO H2 NH3 + CH-COO CO O COO NRibose- P N + COO NH CH COO2 O OH CH O2 P NHCOCH NH2 2 OH Formyl glycinamide-R P Urea Formyl glycinamidine-R P Allantoate Allantoin URATE ADP Xanthine Hypoxanthine Inosine Adenine Adenylo- succinate 5-Amino imidazole-R P 5-Amino-4-imidazole carboxylate-R P 5-Amino-4-imidazole (N-succinylcarboxamide)-R P 5-Aminoimidazole carboxamide-R P Formylamido- imidazole- carboxamide-R P H NCONH2 2 HN H C2 CHO NH RP NH C C C O C CO OC NH NH H N HN H C C O C CH OC NH N N HN Carbamoyl ß-alanine Dihydro- uracil Uracil d-ADP d-ATP GTP GDP XANTHOSINE-P (XMP) TTP TDP ß-Ureido isobutyrate Dihydro thymine Thymine d-UMP d-CMP d-CDP CDP Carbamoyl aspartate Dihydro orotate Orotate Orotidine-P Uridine-P (UMP) UDP 3-Amino- isobutyrate CH C NH2 CHOC NH NCH C O CHOC N H HN CH-CH3 C O OC NH HN CH2 CH2 CH2 C O OC NH HN C O CHOC NH HN C CH3 Methylmalonyl semialdehyde OHCCHCOO CH3 CH2 C O CH-COOOC NH HN CH C O C-COOOC NH HN H NCONHCH CH COO2 2 2 C C C CH RP HC NH NH OOC-CH-CH COO2 N N N CHO NH RP NH OC H C2 2.7.7.43 3.1.3.29 1.1.1.158 5.1.3.13 2.7.1.38 3.2.1.23 3.1.3.29 4.1.3.20 2.7.1.60 5.1.3.14 5.1.3.7 5.1.3.1 2.7.1.4 5.4.2.3 3.1.1.17 1.1.1.49 1.1.1.21 2.7.7.23 3.1.3.251.13.99.11.1.1.19 1.1.3.8 5.3.1.3 2.7.1.53 1.1.1.9 2.7.1.15 2.7.1.17 5.1.3.4 5.1.3.1 2.2.1.2 4.1.2.13 2.7.1.11 2.7.1.47 2.2.1.1 1.2.1.12 1.1.1.29 1.1.1.95 1.3.1.35 1.14.99.25 2.3.1.41 2.3.1.41 2.3.1.41 1.1.1.100 5.3.99.5 4.2.1.60 5.3.99.3 1.14.99.1 1.13.11.34 1.3.1.10 1.3.1.9 1.14.99.5 1.3.1.9 4.2.1.61 4.2.1.60 4.2.1.60 4.2.1.59 4.2.1.58 1.3.1.9 1.3.1.9 6.2.1.3 3.1.2.20 1.1.1.100 5.3.1.1 HOOC-COOH Oxalate Glycolate HOCH CHO2 Glycol aldehyde Ethanolamine-P 2.7.1.30 2.3.1.7 3.7.1.2 4.1.3.5 2.7.8.8 2.1.1.17 2.1.1.71 1.3.1.35 2.7.8.2 3.1.4.3 3.1.4.4 2.7.7.15 3.1.1.5 3.1.4.2 2.7.1.32 2.7.1.82 1.2.4.1 2.3.1.12 1.8.1.4 2.6.1.2 1.4.1.1 4.1.1.1 2.3.1.50 1.1.1.102 3.1.4.12 2.7.8.3 2.4.1.62 3.2.1.46 5.2.1.3 1.2.1.36 2.3.1.76 3.1.1.21 5.2.1.7 5.4.99.7 1.14.99.7 4.3.1.8 4.2.1.75 4.1.1.371.3.3.31.3.3.4 4.99.1.1 2.5.1.29 2.4.1.47 4.1.1.28 2.3.1.5 2.1.1.4 6.3.5.1 6.3.1.5 2.4.2.11 2.7.7.18 2.6.1.5 1.2.1.32 1.13.11.5 2.1.1.28 2.1.2.2 6.3.3.1 3.5.2.5 1.4.1.10 1.7.3.3 1.1.1.204 1.1.3.22 1.1.3.22 4.1.1.28 4.1.1.21 2.1.2.3 2.4.2.1 1.5.99.2 2.1.1.5 2.6.1.22 3.5.2.3 2.6.1.51 1.4.1.7 3.1.3.3 2.6.1.52 2.1.3.2 ACETATE 2.4.2.4 2.1.1.45 RP CH C O CHOC N HN 1.3.1.14 2.4.2.10 4.1.1.23 2.7.7.7 2.7.7.7 2.7.7.7 1.17.4.1 2.7.7.7 2.7.4.14 4.4.1.1 1.6.4.1 1.13.11.20 4.4.1.8 4.2.1.22 1.1.1.27 4.1.1.29 6.3.2.3 6.3.2.2 1.8.1.3 LACTATE Acetaldehyde 2.7.1.24 2.7.7.3 4.1.1.36 Bile Acids CH CH COSCoA3 2 Propanoyl-CoA 1.1.1.31 2.1.3.1 4.1.1.41 5.1.99.1 6.4.1.3 6.3.2.5 2.1.1.14 2.1.1.13 4.6.1.1 CDP-Ethanolamine 1.1.1.35 4.2.1.17 + HO SCH CH(NH )COO2 2 3 3.5.2.7 NHHN CH OOC CHCH CH COO2 2 CMP-N-Acetyl neuraminate CDP-diacyl glycerol CHOLINE Ethanolamine Glyoxylate HISTAMINE 2.3.1.46 Homoserine Tyramine Plant PigmentsTannins Maleyl acetoacetate Fumaryl acetoacetate 5.2.1.2 CH COO2 OH OH OH CH CH NH2 2 2 OH OH CH CH NH2 2 2 Hydroxyphenyl pyruvate α-Tocopherol (Vitamin E) LIGNIN d-GTP OH OH OH O HO OH P OPPT CH3 HO OHOH O NADPH 2.2.1.1 2.7.1.3 1.1.1.45 1.1.1.130 1.10.3.3 1.10.2.1 1.1.1.10 ATP CH CH NH2 2 2 NH HO 5.4.99.5 1.14.16.12.6.1.51.13.11.27 Indole 4.1.99.1 1.13.11.11 OH O OH NH C C CH CH O2 P H HCOO NH2 COO 6.3.5.3 6.3.2.6 4.3.2.2 Guanine DNA 6.3.4.44.3.2.2 C C O C CH HC NH N N HN C C O C CH HC NH N N HN 3.5.3.4 2.4.2.1 2.7.7.62.7.7.6 2.7.7.6 2.7.7.6 2.7.4.6 2.7.4.3 2.7.4.4 2.7.4.6 2.4.2.15 1.1.1.205 6.3.4.1 6.3.5.2 2.7.4.4 3.5.4.3 3.2.2.2 2.4.2.1 3.1.3.5 3.1.4.6 6.3.4.2 1.17.4.1 1.17.4.1 3.5.4.12 2.7.4.8 2.7.4.9 2.7.4.6 2.4.2.4 1.3.1.2 3.5.2.23.5.1.6 3.5.1.6 3.5.2.2 3.5.4.1 Diphospho- mevalonate Mevalonate 3-Oxopentanoyl-CoA 3-Oxoacyl-CoA3-OH-Acyl-CoA2, 3-Enoyl-CoA 2, 3-Hexenoyl-CoA 3-OH-Hexanoyl-CoA Acetoacetyl-CoA3-OH-Butanoyl-CoACrotonoyl-CoA Pentanoyl-CoA 3-OH-Pentanoyl-CoA 1.1.1.35 1.1.1.35 1.1.1.157 1.3.99.3 1.3.99.3 1.3.99.2 1.1.1.35 Odd C Fatty acids Succinylhomoserine CO2 2-OXO ACID Glutamyl-P Glutamine UREA P-CreatineCreatine Creatinine Glycine CITRULLINE Glutamic semialdehyde 2-AMINO ACID Pyrroline-5- carboxylate GlyoxylatePyruvate 4-Hydroxy- 2-oxoglutarate 4-Hydroxy- glutamate 3-Hydroxy- pyrroline- 5-carboxylate Putrescine H NCH CH CH CH NH2 2 2 2 2 2 Spermidine Spermine N -Trimethyllysine66 N -Trimethyl- 3-OH-lysine Carnitine Glutaryl-CoA Saccharopine2-Aminoadipate semialdehyde 2-Aminoadipate2-Oxoadipate Arginino- succinate Guanidoacetate Methylmalonyl-CoA 4.1.2.12 Aspartyl Semialdehyde 2, 3-Dihydro- dipicolinate 1.2.1.11 4.2.1.52 1.3.1.26 Piperideine- 2, 6-dicarboxylate N-Succinyl- 2-amino-6-oxo- pimelate 2.6.1.17 N-Succinyl-2, 6 diaminopimelate Diamino- pimelate 3.5.1.18 3-Methyl- glutaconyl-CoA (CH ) CHCH COSCoA3 2 2(CH ) CHCH COSCoA3 2 2 3-Methyl- crotonyl-CoA Isovaleryl-CoA OxopantoateHCHO OOCCH C = CHCOSCoA2 CH3 CH COCHCOSCoA3 CH3 CH CH=CHCOSCoA3 CH3 CH CH(OH)CHCOSCoA3 CH3 C(OH)CH(OH)COO CH CH3 2 CH3 CH = CCOSCoA2 CH3 HOCH CHCOS-CoA-2 CH3 CH CHCO-SCoA3 CH3 C (OH)CH(OH)COO CH3 CH3 CH CH CHCOSCoA3 2 CH3 CH C = CHCOSCoA3 CH3 ATP 4-Aminobutyrate (GABA) 1.3.99.7 1.5.1.2 1.14.11.2 2.6.1.39 1.2.1.31 1.14.11.8 2.5.1.16 2.5.1.22 4.1.3.16 2.6.1.23 1.5.99.8 1.5.1.2 6.4.1.4 1.3.99.10 4.2.1.33 2.6.1.6 1.1.1.85 Oxoleucine COOH (CH ) CHCHCH(OH)COO3 2 S-Adenosylmethyl thiopropylamine (Decarboxylated SAM) PROLINE Coenzyme A CH C= CHCH3 2 CH3 O CH CH 3 3 HO CH3CH3 CH3 CH C-CH H O3 2 2C PP CH2 CH C= CHCH O2 2 PP CH3 3-P-Glycerol Phosphatidyl ethanolamine CEPHALIN 3.1.4.12 2.7.8.3 Progesterone 1.5.1.12 2.7.3.2 4.2.1.173.1.2.4 2.6.1.32 4.4.1.15 Acetylserine 2.7.7.42.7.1.251.8.99.1 Adenylylsulphate (APS) 2.7.1.39 4.4.1.15 4.1.1.29 4.2.99 .8 2.3.1.30 P-Ribosyl-PP 1.1.1.1 1.2.1.4 Aspartyl-P 5.1.1.7 2.7.1.40 4.1.3.18 4.1.3.18 1.5.1.9 1.14.11.1 CHOLINE 2.1.1.13 1.3.1.2 NHCH CH SH2 2NHCH CH CO2 2OCH C(CH ) CH(OH)CO2 3 2P ADP- NHCH CH SH2 2NHCH CH CO2 2OCH C(CH ) CH(OH)CO2 3 2 P-ADP- NHCH CH SH2 2NHCH CH CO2 2OCH C(CH ) CH(OH)CO2 3 2 1.4.1.8 1.3.99.3 1.3.99.3 1.4.1.9 4.2.1.18 4.1.1.20 1.3.99.7 1.8.99.2 + CH CO-OCH CH(NH )COO2 2 3 2.5.1.6 2.1.1.10 2.1.1.20 1.1.1.3 1.1.1.3 4.2.1.18 4.1.2.5 4.3.1.5 4.2.1.20 2.1.2.1 2.1 .1 .2 0 Glyoxylate 2.1.1.6 1.4.3.4 1.14.18.1 1.14.16.2 Hexanoyl-CoA Butanoyl-CoA 6.3.4.16 6.3.5.5 2.7.2.11 2.1.3.3 NO 1.14.13.39 3.5.3.63.5.3.1 4.3.2.1 4.1.1.17 2.7.7.41 2.6.1.4 1.1.1.100 1.1.1.8 2.3.1.51 2.3.1.15 2.7.8.5 SO - 4 2 1.14.16.4 NH2OOC OOC 4.1.1.25 1.3.1.13 1.3.1.13 2.7.4.6 CYTIDINE- triphosphate (CTP) Cytosine 2.4.2.9 4.1.1.11 2.6.1.18 4.3.1.3 4.2.1.49 3HSO- 1.1.1.105 2.3.1.41 NADPH 1.1.1.22 2.3.1.4 5.5.1.4 3.2.1.26 3.2.1.48 2.6.1.16 1.1.1.14 2.7.7.34 4.2.1.47 2.4.1.68 2.4.1.69 2.4.1.9 5.3.1.8 2.4.1.11 O OPPU CH OH2 CH OH2 HO OH OH HO 2.4.1.21 4.2 .1 .5 2 1.2.1.18 4.2.1.18 O CH C CHOC N HN DP CH C O CHOC N HN RPPP OCH2 H C C H OHOH CH NHN C H CP H O OCH2 C C H OH H OH C H C C C NH2 C CH HC N RP(PP) N N N + P NH2H O OCH2 C C H OH H OH C H C C OC C CH HC N RP N N NHP H OCH2 C C H OHOH CO CH2 C CONH2 C CH HC N RP N N NHP + OOCCH N(CH )2 3 3 Betaine Betaine aldehyde 2.4.1.16 5.1.3.6 2.4.1.33 2.7.7.13 5.4.2.8 5.3.1.8 O OH CH OH2 HO O PHO 2.7.1.28 2.7.1.31 6.3.4.13 5.3.1.1 2.2.1.1 4.1.1.9 3.1.2.11 ß-OH-ß-Methyl- glutaryl-CoA 6.3.4.5 5.3.1.6 2.5.1.21 2.1.1.2 3.5.2.10 6.3.2.13 6.3.2.7-10 2.7.7.27 2.7.7.9 3.5.4.10 C C O C CH OC N RP N N H HN C C O C CH N N N HN RP H N2 C 2.7.4.6 1.17.4.1 2.7.4.6 2.6.1.13 Carbamoyl-P 2.3.1.9 Carnitine 2.6.1.4 2.6.1.44 CH C(OH)CH COSCoA3 2 CH COO2 1.2.3.5 1.1.1.34 2.3.1.16 4.1.3.5 2.3.1.16 4.1.3.4 Menaquinone 4.1 .1 .1 5 2.6.1.19 4.2.1.16 Carnosine CH CH NH2 2 2C NHN C HC H 4.1.1.22 4.3.1.3 Ubiquinone Plastoquinone D-Ribose-5-P NH CH CH(NH )COO2 3HO + O OH OH HO OPPU COO- O OH OH HO OPPU COO- OH H OH HOCH2 C C CO H CO COO- O CHOH CHOHAcNH HO OPC OCO - CH OH2 O CHOH CHOHAcNH HO OH COO CH OH2 O OHOHHOHO CH O2 P O OH ACNH HO OH CH O2 P O OOHHOHO P CH OH2 O OHOH HOHO CH OH2 O OHHO OH 3 CH O2 P O OHHO O NHCOCH3 P CH OH2CH OH2CH OH2 O OHHO OH NH2 CH O2 P O OH HO OH OPPU CH OH2 O O HO OH OH HO P CH OH2 CH OH2 O O HO OH OH O OHOH OH CH OH2 O OHHO OH OH CH2CH OP2 OH H H HOH C C C C OH OHH COO-HOCH2 H OH OHOH C C C CHO HH HOCH2 H OH OHH C C C CHO HOH HOCH2 OH H OHH C C C CHO HOH HOCH2 H OH HOH C C C CHO OHH HOCH2 OH H HOH C C C CHO OHH HOCH2 OH H OHOH C C C CHO HH HOCH2 H OH HOH C C C C OHH H OH COO-POCH2 OH H OH C C CO H POCH2 CH OH2 H OH H C C CO OH HOCH2 CH OH2 CH OH2POCH2 H OH OH C C CO H CH OH2POCH2 OH H H C C CO OH CH OH2 POCH2 H OH OH C C CO H HOCH2 CH OH2 OH H OH C C CO H HOCH2 CH OH2 OH H H C C CO OH HOCH2 CH OH2 H OH OHH C C C HOH HOCH2 CH OH2 OH H OHOH C C C HH HOCH2 CH OH2 H OH HOH C C C C OHH H OH CH OH2HOCH2 H OH OH C C CHO H POCH2 H OH HOH C C C CO OHH HOCH2 CH O2 P H OH OHOH C C C HH HOCH2 CH OH2 H OH OH C C C H CO H HO POCH2 CH OH2 P H OH OH C C C H CO H HO CH O2 POCH2 H OH OH C C H C CHO OH H POCH2POCH2 O OH NH2 OH CH O2 P CHOHCHOPOCH2 HOCH2COCH2OP O OH O OP P OH CH O2 P CHOHCOOPPOCH2 CHOHPOCH2 COO COO OH OHO OH COO CH (CH ) CH(OH)CH COS-CoA3 2 14 2CH (CH ) CH(OH)CH COS3 2 14 2 CH (CH ) COCH COS-CoA3 2 14 2 CH (CH ) COCH COS-CoA3 2 14 2 CH (CH ) COS-CoA3 2 n+2 CH (CH ) CH=CHCOS-CoA3 2 14 CH (CH )3 2 nCH=CHCOS-CoA CH (CH )3 2 5 2CH=CHCH COSACP CH (CH )3 2 6CH=CHCOSACP CH (CH )3 2 6COCH COSACP2CH (CH )3 2 6 2 2CH CH COSACP CH (CH )3 2 2 2 2CH CH COSACP CH CH CH COSACP3 2 2 CH (CH )3 2 6CH(OH)CH COSACP2 CH CH=CHCO.S-ACP3 CH (CH )3 2 2 2COCH COSACP CH3COCH COSACP2 CH (CH )3 2 n 2COCH COSACPCH (CH )3 2 n 2CH(OH)CH COSACP CH (CH )3 2 2 2CH(OH)CH COSACP ACYL-CoA (Mitochondria) CH (CH ) CH CH COSCoA3 2 2 2n CH (CH ) CH=CHCOSCoA3 2 n CH (CH CH(OH)CH COSCoA3 2n CH (CH ) CH CH COSCoA3 2 2 2 2 CH (CH ) CH=CHCOSCoA3 2 2 CH (CH ) COCH COSCoA3 2 2n CH COCH COSCoA3 2 CH (CH ) CH(OH)CH COSCoA3 2 2 2 CH CH(OH)CH COSCoA3 2CH CH=CHCOSCoA3CH CH CH COSCoA3 2 2 CH CH CH CH COSCoA3 2 2 2 Pentenoyl-CoA CH CH CH=CHCOSCoA3 2 CH CH CH(OH)CH COSCoA3 2 2 CH (CH ) COCH COSCoA3 2 2 2 CH CH COCH COSCoA3 2 2 OH OH HO OH O O- CH O-PO2 CH CHOHCH OH2 2 O CH2 CH2 R'-CO-OCH O-CO-R O-PO O- HOCH CH2 2 NH3 +POCH CH2 2NH3 + CPP- OCH CH2 2NH3 + O - CH O-CO-R2 CH O P2 OCH CH2 2NH3 + CH COCH CH N(CH )3 2 2 3 3 HOCH CH N(CH )2 2 3 3 + CH CH2 COO(NH )3 + OH OH CH CH2 COO-(NH )3 + CO NH2 CH CH(NH )COO2 3 + NH OC CO NH OC N H C H H N2 HC CH N N C RP H N2 CH C CHOC N N DP NH2 RPPP CH C CHOC N N NH2 C C C CH RP(P) HC N N N N NH2 H NCOO2 P (CH ) NH2 3 2H N(CH ) NH2 2 3 (CH ) NH2 4 (CH ) NH2 3 2H N(CH ) NH2 2 4 CH -SCH CH CHNH3 2 2 2 Adenosyl + + CH3 CH3 CHCH(NH )COO3 ++ C NHN C HC H CH CH(NH )CH OH2 3 2 + C NHN C HC H CH CH(NH )CH OP2 3 2 C NHN C H HC CH COCH OP2 2 + HSCH CH CH(NH )COO2 2 3 + + SCH CH CH(NH )COO2 2 3 CH CH(NH )COO2 3 RP C O C-COOOC N HN CH 2.4.1.23 CH (CH ) CH=CHCH(OH)CHCH OH3 2 12 2 NH3 + CH (CH ) CH(OH)CHCH OH3 2 14 2 NH3 + CH (CH ) COCHCH OH3 2 14 2 NH3 + GalactoseCH (CH ) CH=CHCH(OH)CHCH O-3 2 12 2 NH3 + 4.1.1.70 H NCONH2 2 OHCCH N(CH )2 3 3 + C-CH3 C O CHOC N DP HN DP CPP-OCH CH N(CH )2 2 3 3 + OCH CH N(CH )2 2 3 3 + 1.2.1.41 UDP-N-Ac-Muramate O O CH CH3 COO- NHAC HO OPPU CH OH2 4.1.3.20 O OH CH3 HO HO OPPG 2.7.7.24 2.4.1.22 2.7.7.12 5.1.3.2 5.3.1.4 Sedoheptulose-PP 3.1.1.28 4.2.1.24 N CH2 CH2 N N N CH3 CH3 CH CH COO CH CH CH2 H C3 H C3H C3 HC C C H H Fe CH2 CH2 COO- - CH3 CH3 CH2 CH2 CH2 H C3 H C3 N H N H N H N H CH CH H C2 C C H2 H2 - CH2 CH2 COO CH2 CH2 COO - H C2 H C2 CH 2 CH 2 OOC COO H N2 N H - - CH2 H C2 H C2 H C2 H2 H2 CH2 CH2 CH2 CH2 CH2 CH2 N H N H N H N H COO COO COO COO C C - - CH2 CH2 COO CH2 CH2 COO- - - - OOC- OOC - CH3 CH3 H C3 H C3 H C2 H2 H2 N H N H N H N H CH2 CH2 CH2 CH2 CH2 C C COO- CH2 CH2 COO CH2 CH2 COO- - COO- COO- CH C(OH)CH CH O3 2 2 PP CH COO2 OHCCOO HOCH COO2 NH2 H NCNHCH COO2 2 + NH2 H NCN(CH )CH COO2 3 2 + NH2 HNCN(CH )CH COO3 2P- + HN C NH CO N CH2 CH3 OOCCHCH COO2 H NCNHCH CH CH CH2 2 2 2 N (NH )3 + COO CHCOOHC CH2HOCH N OOCCH(OH)CH CH(NH )COO2 3 + CHCOO CH2HOCH H C2 N H NH CHCOO CH2CH2 CH2 OOCCH(OH)CH COCOO2 N CHCOO CH2CH2 CH CH COCOO3 OHCCOO + H NCONHCH CH CH CH2 2 2 2 (NH )3 COO H NOCCH CH CH2 2 2 COO(NH )3 + R-CO-COO + COOR-CH(NH )3 + COOH NOCCH CH2 2 (NH3 + OOC-CH-COSCoA CH3 P OOCCH CH2 COO(NH )3 + OOCCH CH CHO2 2 OHCCH CH2 COO(NH )3 + (CH ) NCH CH(OH)CH COO3 3 2 2 + OHCCH CH CH2 2 + COO(NH )3 POOCCH CH CH2 2 + COO(NH )3 OHCCH CH CH CH2 2 2 COO(NH )3 + NH CHCH CH COO2 2 COO CH CH CH CH CH2 2 2 2 COO(NH )3 + H N(CH )2 42 CH(NH )COO3CH(NH3 ++ (CH ) N(CH )3 3 2 3CH CH(NH )COO2 3 + + CH2 C H OOCC N HC CH-COO CH2 C H2 CH-COOOOCC N H C2 OOCCOCH CH CH CH-COO2 2 2CH CH2 2 2 OOCCH CH CONH2 2 OOCCHCH CH CH CH-COO2 2 2 OOCCH CH CONH2 2CH2 2 NH3 + OOCCH-CH CH CH CHCOO2 2 2 NH3 + NH3 + (CH ) CHC(OH)CH3 2 2 COOH COO (CH ) CHCH COCOO3 2 2 + (CH ) CHCH3 2 2 CH(NH )COO3 HOCH CHCOO2 CH3 CHCOCOO CH3 CH3CH COC(OH)CH3 3 COO + POCH CH CH(NH )COO2 2 3 + HOCH CH CH(NH )COO2 2 3 + CH CH CH(NH )COO2 2 3OOCCH CH2COO2 + CH SH2 OOCCH(NH )CH CH CONHCHCONHCH COO3 2 2 2 HOCH C(CH ) COCOO2 3 2 HOCH C(CH ) CH(OH)COO2 3 2 NHCH CH COO2 2HOCH C(CH ) CH(OH)CO3 2)2 3 2 NHCH CH COO2 2OCH C(CH ) CH(OH)CO2 3 2P CH CH3 2 CH3 CH + CH(NH )COO3 CH COC(OH)CH CH3 2 3 COO CHCOCOO CH CH3 2 CH3 NHCHCH SH2 COO NHCH CH CO2 2OCH C(CH ) CH(OH)CO2 3 2P + CH SH2 OOCCH(NH )CH CH CONHCHCOO3 2 2 + Adenosyl SCH CH CH(NH )COO2 2 3 + SCH CH CH(NH )COO2 2 3 + HO SCH CH(NH )COO3 2 3 + + S-CH CH(NH )COO2 3 S-CH CH(NH )COO2 3 + HSCH CH(NH )COO2 3 1.1.1.23 H C NHN C HC CH CHCOO2 NHCOCH CH NH2 2 2 + H C NHN C HC CH CH(NH )COO2 3 CHCH CH COO2 2 NHN CH OC C CH CHCOO NHN CH CH CH COO3 N H OOC CH-COOOC NH2 CH2 H NCH CH COO2 2 2 H NCH2 2 CH3 CHCOO H NCONHCH CHCOO2 2 CH3 C C O CH RP HC N N N HN C CC O CH HCO N N N RP C CH N N H N2 H C C C O CH N N C C CH N N RP H N2 H N2 C O O O P~ ~P O O O O P O O CH2 N N N N O OHOH NH2 HC CH N N N N O O P O O O CH2 OH NH2 HC CH COO CO NH OC N H C H H N2 NH2 OOC-CH-CH COO2 HNCO C CH N N C RPRP H N2 OOC C CH N RP N C H N2 CH=CHCOO OH CH=CHCOO CH COCOO2 CH2 P COO OH O O O COO O CH COO2 O CH COO2-OOC OCH2 CH2 OHH C P HOCH HCOH OC COO COOHO OH OHO NH2 COO OCH NH CH COCOO2 NH CHO CO NH2 OH CH CH(NH )COO2 3 + N COO COO N + COO COO RP O OH OH HO OPPU COO O OH NHCOCH3 HO OPPU COO CH OH2 O O CCH2 NHAC HO OPPU COO CH OH2 O OHHO OH OH COO OOCCH N(CH )2 3 2 Dimethylglycine 1.1.99.1 1.2.1.8 COO HO HO COO O HO OH COO CH(O )PPOCH2 COO CH(OH)HOCH2 COOCOO CH(O )PHOCH2 COO CH =C(O )2 P COO CONH2 Ribose -O - P - O - P - O- Adenosine(P) + N O O O O + COO N Ribose - O - P - O - P - O -Adenosine O O O O II II OH O CH CH2 COO(NH )3 + Epinephrine (Adrenaline) Norepinephrine (Noradrenaline) Normetepinephrine (Normetadrenaline) HOCH CH N(CH )2 2 3 3 + Adenosyl + + SCH CH CH(NH )COO2 2 3 CH3 (CH ) N(CH )3 3 2 3CH CH(NH )COO2 3 + + OH OOCCH CH CH COSCoA2 2 2 OOCCH CH CH NH2 2 2 2 OOCCH CH CH COCOO2 2 2 OOCCH CH CH CH2 2 2 COOCOO(NH )3 ++ HO H HO H H HO H HO H Prostaglandin PGE 2 OH HOCH2 C C CO C COO OHH OHH H - COO OR'-CO-OCH CH O-CO-R2 CH O POCMP2 O CH CH N(CH )2 2 3 + OHOCH CH OPO2 CH OH2 O- CH OPO2 O CH OCH=CHR2 CH CH N(CH )2 2 3 3 + O- CH OPO2 OR'-CO-OCH CH O-CO-R2 3.1.1.32 CH CH N(CH )2 2 3 3 + O- OHOCH CH OPO2 CH O-CO-R2 CH CH N(CH )2 2 3 3 + O- CH CH(NH )COO2 3 + + C NHN C HC H CH CH(NH )CHO2 3 HS 11-cis-Retinal Pi ADP NADP+ GDP- Mannuronate Mannose-6-P Dehydro- shikimate Shikimate RNA d-GDP d-CTP GUANOSINE-P (GMP) ß-Alanine P-Ribosyl-AMP P-Ribulosylformimino 5-aminoimidazole- carboxamide-R P Imidazole acetol-P HS HSO- PANTOTHENATE 3-Isopropyl- malate Succinic semialdehyde 2.4.1.17 Diacyl glycerol 2.3.1.6 1.14.12.1 1.4.4.2 CH CHO3 3.5.4.19 4.2.1.19 3.3.1.1 4.1.1.12 4.1.2.5 COO-2OHCCH 2.1.4.1 2.4.99.7 5.1.3.12 1.1.1.132 4.2.1.46 2.7.1.7 2.4.1.29 2.4.1.21 2.4.1.13 2.4.1.1 etc. 5.4.2.2 2.7.1.6 2.7.7.10 3.1.1.18 4.1.1.34 2.7.1.47 2.7.1.16 3.1.3.9 ADP P-Glucono lactone 1.1.1.44 O O OHHO OH CH O2 P PHENYLALANINETYROSINE TRYPTOPHAN INOSINE-P (IMP) THYMIDINE-P HISTIDINE URIDINE- triphosphate (UTP) CYSTINE CYSTEINE ISOLEUCINE LEUCINE LYSINE ORNITHINE ARGININE HYDROXY PROLINE PHOSPHATIDYL SERINEPhosphatidyl inositol LECITHIN SPHINGOMYELIN STEROIDS Pregnenolone 2.7.6.1 2.4.2.14 6.3.4.7 5.3.1.9 3.1.3.11 1.2.1.13 2.7.2.3 H OH OH C C C H CO OH C H H OH POCH2 CH O2 P 5.4.2.1 ADP 4.2.1.11 Endoplasmic Reticulum 1.1.1.100 3.1.1.3 Phosphatidate 2.3.1.39 4.2.1.17 4.2.1.17 4.2.1.55 1.1.1.79 1.2.1.21 1.4.3.8 1.1.1.32 2.7.1.36 2.7.4.2 4.1.1.33 2.5.1.1 2.5.1.10 2.7.8.5 2.7.8.1 4.1.1.65 2.7.7.14 1.3.99.7 PO O CH (CH ) CH=CHCH(OH)CHCH O3 2 12 2 NHAcyl CH CH N(CH )2 2 3 3 + O- 3.5.1.23 1.13.11.21 2.5.1.32 1.1.1.105 2.4.2.19 1.2.1.32 METHIONINE 4.1.3.27 4.2.1.51 1.14.17.1 1.14.18.1 1.14.13.11 Glycinamide- ribosyl-P 4.2.1.22 3-Oxohexanoyl-CoA THREONINE 1.2.1.25 1.2.1.25 1.2.1.25 1.5.1.7 - 10 GLUTAMATE 2.3.1.38 ATP NADH SUCROSE ADENOSINE-P (AMP) Triacylglycerol FAT RNA CH3 CH2 OC-COOOH COO CH CH2 COO(NH )3 + GLYCOPROTEINS GANGLIOSIDES MUCINS 4.1.2.- 2.6.1.- GLUCOSE O-Acyl-carnitine O-Acyl-carnitine OH O- - R-CO-OCH R'-CO-OCH R'-CO-OCH O HCO-CO-R CH CH(OH)CH O-P-OCH2 2 2 CH O-CO-R’2 OR'-CO-OCH O- CH O-CO-R2 CH O-PO2 O- 2.7.8.11 H NCH CH CH CH2 2 2 2 COO(NH )3 + 2.3.1.20 3.1.3.4 2.7.1.107 NH2 + + H NCNHCH CH CH CH2 2 2 2 COO(NH )3 H OH HOH C C C CO OHH HOCH2 CH OH2 R-CH2COO CH O-CO-R2 CH O-CO-R"2 R’-CO-OCH OH O CH CHNH2 3 + OR'-CO-OCH O- CH O-CO-R2 CH O PO2 COO OOCCH CH CH2 2 COO(NH )3 + CH CH(OH)CH(NH )COO3 3 O OHHO OH OH CH OH2CH OH2 NH CH O-CO-R2 1.3.1.13 4.1.1.28 Malonic semi- aldehyde 2.7.2.4 2.1.3.3 3.5.1.2 6.3.1.2 6.3 .5 .5 Carbohydrates Biosynthesis Degradation Amino Acids Biosynthesis Degradation Lipids Biosynthesis Degradation Purines & Pyrimidines Biosynthesis Degradation Biosynthesis Degradation Vitamins Co-enzymes & Hormones Pentose Phosphate Pathway Photosynthesis Dark Reactions COMPARTMENTATION The "Backbone" of metabolism involves GLYCOLYSIS in the CYTOPLASM, the TCA CYCLE (mainly) in the Mitochondrial matrix and ATP FORMATION spanning the MITOCHONDRIAL INNER MEMBRANE An electron flow (an electric current) generated from NADH and UQH2 drives the translocation of protons from the matrix to the intermembrane space. 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