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Mapa metabólico, Resumos de Química

Mapa com todos caminhos metabólicos, ciclos bioquímicos resumidos e simplificados em TODAS ROTAS (catalíticas e metabólicas / síntese e degradação) . Fonte: Sigma --[em inglês]--

Tipologia: Resumos

Antes de 2010

Compartilhado em 12/12/2010

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bg1
2H
+
H+
OXALOACETATE
PYRUVATE
SUCCINYL-CoA
GLUTARATE
CITRATE
MALATE
2-OXO-
ASPARTATE
NO2-
NO3-
N2
NH4
CH
3
COSCoA
ACETYL-CoA
HOH
CO2
NAD
T
R
A
N
S
A
M
I
N
A
T
I
O
N
2H
+
2H+
+
CO2
5-Amino-
levulinate
Glycine
H+
H+
H+
H+
H+
H+
c
H+H+
a
F0
F1
F1
β
2
1
α
β
α
γ
1
0
c
-
s
u
b
-
u
n
i
t
s
A
D
P
+
P
i
a
H+
3
.
6
.
1
.
3
4
H
+
-
t
r
a
n
s
p
o
r
t
i
n
g
A
T
P
s
y
n
t
h
a
s
e
α
δ
F6
oscp
AT P
ADP +Pi
FUMARATE
UQH2
UQ
UQH2
NADH+H+
CH2COO-
C(OH)COO-
CH2COO-
CH(OH)COO-
CHCOO-
CH2COO-
-OOCCOCH2CH2COO-
-OOCCH2CH2CO.SCoA
-OOCCOCH2COO-
CH3CH(OH)CH
2
CO.SCoA
-OOCCH=CHCOO-
C
C
C
C
Glyoxylate
Cycle
-OOCCHO
GTP
GDP
ATP
+
HEME Protoporphyrinogen Coproporphyrinogen Uroporphyrinogen Porphobilinogen
5-Amino-
levulinate
COO-
CH2
CH2
H2NCH2C=O
FADH2
FAD
Cyt.b
Fe-S
SUCCINATE
II
CH
3
COCOO-
PYRUVATE
Pi
XY
Cyt.c
1
Fe-S
2e-
2e- 1e-
1e-
III
2UQ UQ
UQH2
2UQH2
2UQ.
_
UQ.
_
Cyt.bLCyt.bH
Cyt.c
IV
Cu
A
Cu
B
Cu
A
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
1.18.6.1
2.3.1.37
1.10.2.2
1.10.2.2
γ
ε
δ
β
H
+
3
3
β
A
T
P
ADP
E
N
D
E
R
G
O
N
I
C
R
E
A
C
T
I
O
N
1.6.5.3
I
FMNH2
FMN I
1.6. 5.3
2Fe -S
(5 Clusters)
H+H+
H+H+
AT P
4H
+
2H
+
2H
+
or
H+
PHOTO-
SYSTEM
l
O2
3.6.1.34
NADP+
Glyceraldehyde
Ribulose-1,5-bis-P
2
β
8
8
H+
c
3
2
ε
a
3
2
α1
α
ε
α
β
2
1
3
α
α
β
3
α
β
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-
C
y
c
l
i
c
P
h
o
t
o
p
h
o
s
p
h
o
r
y
l
a
t
i
o
n
PQ
PHOTO-
SYSTEM
II
Cyt bc
N
o
n
-
c
y
c
l
i
c
e
l
e
c
t
r
o
n
f
l
o
w
2e-
2e-
Mn
2e-
*
Protons from Water
H2O
H+
H+
2H+
2H+
γ
ATP synthase
CO2
Fixation
H+
ADP
P
i
H
+
NADPH+H+
e
e
e
ATP
THYLAKOID MEMBRANE
CHLOROPLAST OUTER MEMBRANE
THYLAKOID LUMEN
STROMA
(
e
l
e
c
t
r
i
c
c
u
r
r
e
n
t
)
P680
Chl.a
Q
A
Q
B
Pheophytin
P700
Chl.A
0
A
1
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
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S
P
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R
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N
E
S
C
A
T
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C
H
O
L
A
M
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N
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S
A
R
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M
A
T
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C
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M
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A
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hvVISION
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
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X
O
S
E
S
P
O
L
Y
S
A
C
C
H
A
R
I
D
E
S
COCH CH(NH )COO
23
+
FOLIC
ACID
C1
POOL
VALINE
AT P
AT P
4.1.1.4 1.1.1.30
CH COCH
33
CH COCH COO
32
CH CH(OH)CH COO
32
3-OH-ButyrateAcetone
Acetoacetate
KETONE BODIES
HYALURONIC ACID DERMATA NBLOOD 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
CH3O
OPPT
OOH
OH
O
OH
ACNH
HO OH
O
OHHO OPPU
NHAC
OH
OH OH
OH
HO
OH
NHCOCH
OHHO
O
OPPG
CH OH
2
HO
P
UDP-N-Ac-
Glucosamine
pyruvate
N-Ac-Mannosamine-6-PUDP-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
HHH
O
HOCH2CCCCCO
OH OHH OH
HH
O
HOCH2CCCCOCO
OHH
H
OH H
CC
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 OH
2
CH OH
2
HOCH
CH OH
2
CH O
2
HOCH P
Glycerol
UDP-Galactose
UDP-Sugars
CH CH OH
32
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-PN-(5-P-Ribosyl)
anthranilate Anthranilate
Catechol
NH
Indole-
acetaldehyde
NH
CH CHO
2
Indolepyruvate
NH
C-CH(OH)CH(OH)CH O
2P
CH
2-Aminomuconate-
6-semialdehyde
CH CH NH
222
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-PShikimate-5
enolpyruvate 3-PChorismate
PEP
2.7.1.71
1.4.1.19
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 )COOH
23
+
Histidinol-PHistidinolHistidinal 3.1.3.15 2.6.1.91.1.1.23
3.6.1.31
5.3.1.16
2.4.2.17
Asparagine
ALANINE
3-Sulphinyl
pyruvate
Oxobutyrate
2-Aceto-2-
hydroxy-
butyrate
O-Phospho-
homoserine
HO SCH CH NH
2222
Hypotaurine HO SCH CH NH
3222
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 COCOO
32
+
CH CH(NH )COO
33
CH CH(OH)COO
3
HO SCH COCOO
22
OCHCOCOO
2
P
OCHCH(NH )COO
23
P
HOCH COCOO
2
HOCH CH(NH )COO
23
+
+
OH
CH COCOO
2
COO
OH
OH
O
COO
OH
OH
HO P
COO
OH
OH
O
CH2
P
COO
O-C-COO
OH
OOH
OOC CH COCOO
2
NH
HOC-CH(OH)CH(OH)CH2OP
CH
COO
NH2
COO
OH NH2
COO
COO
OCH
OOCCH NHCH
23
CH (CH ) COS-ACP
3214 CH (CH ) COSCoA
3214
CH (CH ) CH=CHCO-S-ACP
322
CH CH=CHCO-S-ACP
3CH CH(OH)CH COS-ACP
32
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-ACP
2
Malonyl-ACP
HOOCCH CO-SCoA
2
Malonyl-Co-A
CH CO-S-ACP
3
Acetyl-ACP
CH O-CO-R
2
CH OH
2
R’-CO-OCH
FATTY ACID
ACYL-CoA
(Cytosol)
CH O-CO-R
2
CH O
2
R’-CO-OCH
P
Cardiolipin Phosphatidylglycerol
Acetylcholine
Glycerophosphocholine
Lysolecithin
Choline
plasmalogen
CDP-choline Choline-P
Mevaldate
CH (CH ) CH=CHCH(OH)CHCH OH
3212 2
Dehydrosphinganin Sphinganin 4-Sphingenin Psychosine
Acyl-CoA
Acyl-CoA
CerebrosideGalactose
CH (CH ) CH=CHCH(OH)CHCH O-
3212 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 O
32
PP
CH3
Ceramide
Gangliosides
NHCOR
CH O
2PP
OPP
CH2
CHOLESTEROL
CH C(OH)CH CH OH
322
CH COO
2
CH C(OH)CH CHO
32
CH COO
2
NADP+
Dehydroascorbate
OH
HO
HOCH2CCCCCO
OHH OH
OH
HO
HOCH2CCCO CO CO
H
NAD+
Pi
ADP
ADP
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 OH
2
CHO
CH OH
2
CH3
CH O
3
CH O
3n
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 NHCOCH
22 3
HO
NH
CH CH NHCOCH
22 3
CH O
3
+
NAD( P)
NICOTINATE
N-Acetyl-serotonin
2.4.2.19
Dopamine Dopa
Dopaquinone
THYROXINEMELANIN
OH OH
CHOHCH NHCH
23
OHOH
CHOHCH NH
22
4-OH-3-Methoxy-
phenylglycol
CHOHCH NH
22
OHOCH3
OCH3CHOHCH OH
2
OH
OCH3
4-OH-3-Methoxy-
D-mandelate
Cyclic AMP AT P
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
N
H
O
O
O
O
CH OH
2
OH OCH3
CH(OH)COO
H2
NH3
+CH-COO
C
O
O
COO
N
Ribose-P
N
+
COO
NH
CH COO
2
O
OH
CH O
2P
NHCOCH NH
22
OH Formyl
glycinamide-R P
Urea
Formyl
glycinamidine-R P
Allantoate Allantoin URATE
ADP
Xanthine Hypoxanthine
Inosine
Adenine
Adenylo-
succinate
5-Amino
imidazole-R P5-Amino-4-imidazole
carboxylate-R P5-Amino-4-imidazole
(N-succinylcarboxamide)-RP5-Aminoimidazole
carboxamide-R P
Formylamido-
imidazole-
carboxamide-R P
H NCONH
22
HN
HC
2CHO
NH RP
NH
C
C
C
O
CCO
OC NH
NH
H
N
HN
H
C
C
O
CCH
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-PUridine-P
(UMP) UDP
3-Amino-
isobutyrate
CH
C
NH
2
CH
OC NH
N
CH
C
O
CH
OC NH
HN
CH-CH3
C
O
OC NH
HN CH2
CH2
CH2
C
O
OC NH
HN
C
O
CH
OC NH
HN CCH3
Methylmalonyl
semialdehyde
OHCCHCOO
CH3
CH2
C
O
CH-COO
OC NH
HN CH
C
O
C-COO
OC NH
HN
H NCONHCH CH COO
222
C
C
CCH
RP
HC NH
NH
OOC-CH-CH COO
2
N
N
N
CHO
NH RP
NH
OC
HC
2
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
3.1.3.25
1.13.99.1
1.1.1.19
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 CHO
2
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
4.1.1.37
1.3.3.31.3.3.4
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
CH
OC 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 COSCoA
32
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 )COO
223
3.5.2.7
NH
HN CH
OOC CHCHCH COO
22
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 COO
2
OH
OH
OH
CH CH NH
222
OH OH
CH CH NH
222
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
AT P
CH CH NH
222
NH
HO
5.4.99.5
1.14.16.1
2.6.1.5
1.13.11.27
Indole
4.1.99.1
1.13.11.11
OH
OOH
NH CCCH
CH O
2
P
HH
COO
NH2
COO
6.3.5.3 6.3.2.6 4.3.2.2
Guanine
DNA
6.3.4.4
4.3.2.2
C
C
O
CCH
HC NH
N
N
HN C
C
O
CCH
HC NH
N
N
HN
3.5.3.4
2.4.2.1
2.7.7.6
2.7.7.6
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
3.5.2.2
3.5.1.6
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-CoA
3-OH-Butanoyl-CoA
Crotonoyl-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-Creatine
Creatine 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 NH
222222
Spermidine
Spermine
N -Trimethyllysine
6
6
N -Trimethyl-
3-OH-lysine
Carnitine
Glutaryl-CoA Saccharopine2-Aminoadipate
semialdehyde
2-Aminoadipate
2-Oxoadipate
Arginino-
succinate
Guanidoacetate
Methylmalonyl-CoA
4.1.2.12
Aspartyl
Semialdehyde 2, 3-Dihydro-
dipicolinate
1.2.1.11
4.2.1.52 1.3.1.26Piperideine-
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 COSCoA
32 2
(CH ) CHCH COSCoA
32 2
3-Methyl-
crotonyl-CoA Isovaleryl-CoA
Oxopantoate
HCHO
OOCCH C = CHCOSCoA
2
CH3
CH COCHCOSCoA
3
CH3CH CH=CHCOSCoA
3
CH3
CH CH(OH)CHCOSCoA
3
CH3
C(OH)CH(OH)COO
CH CH
32
CH3
CH = CCOSCoA
2
CH3
HOCH CHCOS-CoA-
2
CH3CH CHCO-SCoA
3
CH3
C (OH)CH(OH)COO
CH3
CH3
CH CH CHCOSCoA
32
CH3
CH C = CHCOSCoA
3
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)COO
32
S-Adenosylmethyl
thiopropylamine
(Decarboxylated SAM)
PROLINE
Coenzyme A
CH C= CHCH
32
CH3
O
CH
CH
3
3
HO CH3
CH3
CH3
CH C-CH HO
322
CPP
CH2
CH C= CHCH O
22
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
4.2.1.17
3.1.2.4
2.6.1.32
4.4.1.15
Acetylserine 2.7.7.4
2.7.1.25
1.8.99.1 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 SH
22
NHCH CH CO
22
OCH C(CH ) CH(OH)CO
232
P
ADP- NHCH CH SH
22
NHCH CH CO
22
OCH C(CH ) CH(OH)CO
232
P-ADP- NHCH CH SH
22
NHCH CH CO
22
OCH C(CH )CH(OH)CO
232
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 )COO
223
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
2.1.1.20
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
3.5.3.6
3.5.3.1
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
NH2
OOC
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
3
HSO-
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 OH
2
CH OH
2
HO OH
OH
HO
2.4.1.21
4.2.1.52
1.2.1.18
4.2.1.18
O
CH
C
CH
OC N
HN
DP
CH
C
O
CH
OC N
HN
RPPP
OCH2
H
CC
H
OHOH
CH
N
HN C
H
C
P
H
O
OCH2CC
H
OH
H
OH
C
H
CC
C
NH2
CCH
HC NRP(PP)
N
N
N
+
P
NH2
H
O
OCH2CC
H
OH
H
OH
C
H
CC
OC
CCH
HC NRP
N
N
NH
P
H
OCH2CC
H
OHOH
CO CH2C
CONH2
CCH
HC NRP
N
N
NH
P
+
OOCCH N(CH )
233
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 OH
2
HO
OP
HO
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
CCH
OC NRP
N
NH
HN
C
C
O
CCH
N
N
N
HN
RP
HN
2C
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 COSCoA
32
CH COO
2
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
4.1.1.15
2.6.1.19
4.2.1.16
Carnosine
CH CH NH
222
C
NH
NC
HC
H
4.1.1.22
4.3.1.3
Ubiquinone
Plastoquinone
D-Ribose-5-P
NH
CH CH(NH )COO
23
HO +
O
OH
OH
HO
OPPU
COO-
O
OH
OH
HO OPPU
COO-
OH
HOH
HOCH2CC CO
H
CO COO-
O
CHOH
CHOH
AcNH
HO
OPC
O
CO -
CH OH
2
O
CHOH
CHOH
AcNH
HO
OH
COO
CH OH
2
O
OH
OHHO
HO
CH O
2P
O
OH
ACNH
HO OH
CH O
2P
O
O
OHHO
HO P
CH OH
2
O
OH
OHHO
HO
CH OH
2
O
OHHO OH
3
CH O
2P
O
OH
HO O
NHCOCH3
P
CH OH
2
CH OH
2
CH OH
2
O
OH
HO OH
NH2
CH O
2P
O
OH
HO
OH
OPPU
CH OH
2
O
O
HO
OH
OH
HO
P
CH OH
2
CH OH
2O
O
HO
OH
OH
O
OH
OH
OH
CH OH
2
O
OH
HO
OH
OH
CH2
CH OP
2
OH
HHHOH
CCCC
OH OHH
COO-
HOCH2
H
OH OHOH
CCCCHO
H
H
HOCH2
H
OH OHH
CCC CHO
HOH
HOCH2
OH
HOHH
CCCCHO
HOH
HOCH2
H
OH HOH
CCCCHO
OHH
HOCH2
OH
HH
OH
CCCCHO
OHH
HOCH2
OH
HOHOH
CCCCHO
HH
HOCH2
H
OH HOH
CCCC
OHH H
OH
COO-
POCH2
OH
HOH
CCCO
H
POCH2CH OH
2
H
OH H
CCCO
OH
HOCH2CH OH
2
CH OH
2
POCH2
H
OH OH
CCCO
H
CH OH
2
POCH2
OH
HH
CCCO
OH
CH OH
2
POCH2
H
OH OH
CCCO
H
HOCH2CH OH
2
OH
HOH
CCCO
H
HOCH2CH OH
2
OH
HH
CCCO
OH
HOCH2CH OH
2
H
OH OHH
CCC
H
OH
HOCH2CH OH
2
OH
HOHOH
CCC
HH
HOCH2CH OH
2
H
OH HOH
CC
CC
OHH H
OH
CH OH
2
HOCH2
H
OHOH
CC
CHO
H
POCH2
H
OH H
OH
CCCCO
OHH
HOCH2CH O
2P
H
OH OHOH
CCC
HH
HOCH2CH OH
2
H
OH OH
CCC
H
CO
H
HO
POCH2CH OH
2
P
H
OH OH
CCC
H
CO
H
HO
CH O
2P
OCH2
H
OH OH
CC
H
C CHO
OH
H
POCH2
POCH2
O
OH
NH2
OH
CH O
2P
CHOHCHO
POCH2
HOCH2COCH2OP
O
OH
OOPP
OH
CH O
2P
CHOHCOOP
POCH2
CHOH
POCH2COO
COO
OH
O
HO OH
COO
CH (CH ) CH(OH)CH COS-CoA
3214 2
CH (CH ) CH(OH)CH COS
3214 2
CH (CH ) COCH COS-CoA
3214 2
CH (CH ) COCH COS-CoA
3214 2
CH (CH ) COS-CoA
32
n+2
CH (CH ) CH=CHCOS-CoA
3214
CH (CH )
32nCH=CHCOS-CoA
CH (CH )
3252
CH=CHCH COSACP
CH (CH )
326CH=CHCOSACP
CH (CH )
326COCH COSACP
2
CH (CH )
32622
CH CH COSACP
CH (CH )
32222
CH CH COSACP
CH CH CH COSACP
322
CH (CH )
326CH(OH)CH COSACP
2
CH CH=CHCO.S-ACP
3
CH (CH )
3222
COCH COSACP
CH3COCH COSACP
2
CH (CH )
32n2
COCH COSACPCH (CH )
32n2
CH(OH)CH COSACP
CH (CH )
3222
CH(OH)CH COSACP
ACYL-CoA
(Mitochondria)
CH (CH )CHCH COSCoA
3222n
CH (CH ) CH=CHCOSCoA
32nCH (CH CH(OH)CH COSCoA
3 2n
CH (CH )CHCH COSCoA
32222CH (CH ) CH=CHCOSCoA
322
CH (CH ) COCH COSCoA
32 2n
CH COCH COSCoA
32
CH (CH ) CH(OH)CH COSCoA
3222
CH CH(OH)CH COSCoA
32
CH CH=CHCOSCoA
3
CH CH CH COSCoA
322
CH CH CH CH COSCoA
3222 Pentenoyl-CoA
CH CH CH=CHCOSCoA
32 CH CH CH(OH)CH COSCoA
32 2
CH (CH ) COCH COSCoA
3222
CH CH COCH COSCoA
32 2
OH OH
HO OH
O
O-
CH O-PO
2
CH CHOHCH OH
22
O
CH2
CH2
R
'
-CO-OCH
O-CO-R
O-PO
O-
HOCH CH
22
NH3
+
POCH CH
22
NH3
+
CPP-OCH CH
22
NH3
+
O
-
CH O-CO-R
2
CH O P
2OCH CH
22
NH3
+
CH COCH CH N(CH )
32233
HOCH CH N(CH )
22 33
+
CH CH
2COO
(NH )
3
+
OH
OH
CH CH
2COO-
(NH )
3
+
CO
NH2
CH CH(NH )COO
23
+
NH
OC CO
NH
OC N
H
C
H
HN
2
HC CH
N
N
C
RP
HN
2
CH
C
CH
OC N
N
DP
NH2
RPPP
CH
C
CH
OC N
N
NH2
C
C
CCH
RP(P)
HC N
N
N
N
NH2
H NCOO
2P
(CH )NH
23 2
H N(CH )NH
223(CH)NH
24
(CH )NH
23 2
H N(CH )NH
224
CH -SCH CH CHNH
3222
Adenosyl
+
+
CH3
CH3
CHCH(NH )COO
3
++
C
NH
NC
HC
H
CH CH(NH )CH OH
232
+
C
NHN C
HC
H
CH CH(NH )CH OP
232C
NHN C
H
HC CH COCH OP
22
+
HSCH CH CH(NH )COO
22 3
+
+
SCH CH CH(NH )COO
22 3
CH CH(NH )COO
23
RP
C
O
C-COO
OC N
HN CH
2.4.1.23
CH (CH ) CH=CHCH(OH)CHCH OH
3212 2
NH3
+
CH (CH ) CH(OH)CHCH OH
3214 2
NH3
+
CH (CH ) COCHCH OH
3214 2
NH3
+
Galactose
CH (CH ) CH=CHCH(OH)CHCH O-
3212 2
NH3
+
4.1.1.70
H NCONH
22
OHCCH N(CH )
233
+
C-CH3
C
O
CH
OC NDP
HN
DP
CPP-OCH CH N(CH )
22 33
+
OCH CH N(CH )
22 33
+
1.2.1.41
UDP-N-Ac-Muramate
O
O
CH CH
3
COO-
NHAC
HO
OPPU
CH OH
2
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
HC
3
HC
3
HC
3
HC
C
C
H
H
Fe
CH2
CH2
COO--
CH3
CH3
CH2
CH2
CH2
HC
3
HC
3NH
NH
N
H
N
H
CH
CH
HC
2
C
C
H2
H2
-
CH2
CH2
COO
CH2
CH2
COO -
HC
2
HC
2
CH2
CH2
OOC
COO
HN
2
N
H
-
-
CH2
HC
2
HC
2
HC
2
H2
H2
CH2CH2CH2
CH2
CH2
CH2
NH
NH
N
H
N
H
COO
COO
COOCOO
C
C
-
-
CH2
CH2
COO
CH2
CH2
COO--
-
-
OOC
-
OOC
-
CH3
CH3
HC
3
HC
3
HC
2
H2
H2
NH
NH
N
H
N
HCH2
CH2
CH2
CH2
CH2
C
C
COO-
CH2
CH2
COO
CH2
CH2
COO
--
COO-
COO-
CH C(OH)CH CH O
322PP
CH COO
2
OHCCOO
HOCH COO
2
NH2
H NCNHCH COO
22
+NH2
H NCN(CH )CH COO
232
+NH2
HNCN(CH )CH COO
32
P-
+
HN CNH CO
NCH
2
CH
3
OOCCHCH COO
2
H NCNHCH CH CH CH
2222
N(NH )
3
+COO
CHCOO
HC
CH2
HOCH
N
OOCCH(OH)CH CH(NH )COO
23
+
CHCOO
CH2
HOCH
HC
2N
H
NH
CHCOO
CH2
CH2
CH2
OOCCH(OH)CH COCOO
2
N
CHCOO
CH2
CH2
CH
CH COCOO
3OHCCOO
+
H NCONHCH CH CH CH
2222
(NH )
3COO
H NOCCH CH CH
222COO
(NH )
3
+
R-CO-COO
+
COO
R-CH(NH )
3
+
COOH NOCCH CH
22
(NH3
+
OOC-CH-COSCoA
CH3
POOCCH CH
2COO
(NH )
3
+
OOCCH CH CHO
22
OHCCH CH
2COO
(NH )
3
+
(CH ) NCH CH(OH)CH COO
33 22
+
OHCCH CH CH
22+COO
(NH )
3
POOCCHCH CH
22+COO
(NH )
3
OHCCH CH CH CH
222COO
(NH )
3
+NH CHCH CH COO
22
COO
CH CH CH CH CH
2222 COO
(NH )
3
+
HN(CH)
242CH(NH)COO
3
CH(NH3
++
(CH ) N(CH )
33 23
CH CH(NH )COO
23
++
CH2
C
H
OOCC N
HC CH-COO CH2
C
H2
CH-COO
OOCC N
HC
2
OOCCOCH CH CH CH-COO
222
CH CH
222
OOCCH CH CONH
22 OOCCHCH CH CH CH-COO
222
OOCCH CH CONH
22
CH
22
NH3
+OOCCH-CH CH CH CHCOO
222
NH3
+
NH3
+
(CH ) CHC(OH)CH
32 2
COOH
COO (CH ) CHCH COCOO
32 2
+
(CH ) CHCH
32 2CH(NH)COO
3
HOCH CHCOO
2
CH3
CHCOCOO
CH3
CH3
CH COC(OH)CH
33
COO
+
POCH CH CH(NH )COO
22 3+
HOCH CH CH(NH )COO
22 3
+
CH CH CH(NH )COO
22 3
OOCCH CH2COO
2
+CH SH
2
OOCCH(NH )CH CH CONHCHCONHCH COO
3222
HOCH C(CH ) COCOO
232
HOCH C(CH )CH(OH)COO
232
NHCH CH COO
22
HOCH C(CH ) CH(OH)CO
32
)
232
NHCH CH COO
22
OCH C(CH )CH(OH)CO
232
P
CH CH
32
CH3
CH +
CH(NH )COO
3
CH COC(OH)CH CH
323
COO CHCOCOO
CH CH
32
CH3
NHCHCH SH
2
COO
NHCH CH CO
22
OCH C(CH ) CH(OH)CO
232
P
+CH SH
2
OOCCH(NH )CH CHCONHCHCOO
322
+
Adenosyl
SCH CH CH(NH )COO
22 3
+
SCH CH CH(NH )COO
22 3
+
HO SCH CH(NH )COO
323
+
+
S-CH CH(NH )COO
23
S-CH CH(NH )COO
23 +
HSCH CH(NH )COO
23
1.1.1.23
H
C
NH
NC
HC CH CHCOO
2NHCOCH CH NH
222+
H
C
NHN C
HC CH CH(NH )COO
23
CHCH CH COO
22
NH
NCH
OC CCH CHCOO
NH
NCH
CH
CH COO
3
N
H
OOC
CH-COO
OC
NH
2
CH2
H NCH CH COO
222
H NCH
22
CH3
CHCOO H NCONHCH CHCOO
22
CH3
C
C
O
CH
RP
HC N
N
N
HN
C
C
C
O
CH
HCO N
N
NRP
CCH
N
N
HN
2
HC
C
C
O
CH
N
N
C
CCH
N
N
RP
HN
2
HN
2C
O
O
OP
~~
PO
O
O O
PO
O
CH2
N
N
N
N
O
OHOH
NH2
HC CH
N
N
N
N
O
O
PO O
O
CH
2
OH
NH2
HC CH
COO CO
NH
OC N
H
C
H
HN
2NH2
OOC-CH-CH COO
2
HNCO CCH
N
N
C
RPRP
HN
2
OOC CCH
NRP
N
C
HN
2
CH=CHCOO
OH
CH=CHCOO
CH COCOO
2
CH2
P
COO
OH
O
O
O
COO
O
CH COO
2
O
CH COO
2
-OOC
OCH2CH2
OH
HC
P
HOCH HCOH
OC COO
COO
HO
OH
OH
O
NH2
COO
OCH
NH
CH COCOO
2NH CHO
CO
NH2
OH
CH CH(NH )COO
23
+
N
COO
COO
N
+
COO
COO
RP
O
OH
OH
HO OPPU
COO
O
OH
NHCOCH3
HO
OPPU
COO
CH OH
2
O
O
CCH2NHAC
HO OPPU
COO
CH OH
2
O
OH
HO OH
OH
COO
OOCCH N(CH )
232
Dimethylglycine
1.1.99.1
1.2.1.8
COO HO HO COO
O
HO OH
COO
CH(O )
PPOCH2COO CH(OH)
HOCH2COOCOO
CH(O )P
HOCH2COO
CH =C(O )
2PCOO
CONH2
Ribose -O - P - O - P - O- Adenosine(P)
+
NO
O
O
O
+
COO
NRibose - O - P - O - P - O -Adenosine
O
O
O
O
II
II OH
O
CH CH
2COO
(NH )
3
+
Epinephrine
(Adrenaline) Norepinephrine
(Noradrenaline)
Normetepinephrine
(Normetadrenaline)
HOCHCH N (CH )
2233
+
Adenosyl +
+
SCH CH CH(NH )COO
22 3
CH3
(CH ) N(CH )
33 23
CH CH(NH )COO
23
++
OH
OOCCH CH CH COSCoA
222
OOCCH CH CH NH
2222
OOCCH CH CH COCOO
222 OOCCH CH CH CH
222COOCOO
(NH )
3
++
HO H
HO H
H
HO H
HO H
Prostaglandin PGE2
OH
HOCH2CCCO C COO
OHH
OH
HH
-
COO
O
R
'
-CO-OCH
CH O-CO-R
2
CH O POCMP
2O
CH CH N(CH )
22 3
+
O
HOCH
CH OPO
2
CH OH
2
O-
CH OPO
2
O
CH OCH=CHR
2
CH CH N(CH )
22 33
+
O-CH OPO
2
O
R'-CO-OCH
CH O-CO-R
23.1.1.32
CH CH N(CH )
22 33
+
O-
O
HOCH
CH OPO
2
CH O-CO-R
2
CH CH N(CH )
22 33
+
O-
CH CH(NH )COO
23
+
+
C
NH
NC
HC
H
CH CH(NH )CHO
23
HS
11-cis-Retinal
Pi
ADP
NADP+
GDP-
Mannuronate
Mannose-6-PDehydro-
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 CHO
3
3.5.4.19
4.2.1.19
3.3.1.1
4.1.1.12
4.1.2.5
COO-
2
OHCCH
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
OH
HO
OH
CH O
2P
PHENYLALANINETYROSINE
TRYPTOPHAN
INOSINE-P
(IMP)
THYMIDINE-P
HISTIDINE
URIDINE-
triphosphate
(UTP)
CYSTINE CYSTEINE
ISOLEUCINE
LEUCINE
LYSINE
ORNITHINE
ARGININE HYDROXY
PROLINE
PHOSPHATIDYL
SERINE
Phosphatidyl
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
CCC
H
CO
OH
C
H
H
OH
POCH2CH O
2P
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 O
3212 2
NHAcyl
CH CH N(CH )
22 33
+
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
AT P
NADH
SUCROSE
ADENOSINE-P
(AMP)
Triacylglycerol
FAT
RNA
CH3
CH2
OC-COO
OH
COO
CH CH
2COO
(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-OCH
222
CH O-CO-R’
2
O
R
'
-CO-OCH
O-
CH O-CO-R
2
CH O-PO
2O-
2.7.8.11
H NCH CH CH CH
2222 COO
(NH )
3
+
2.3.1.20
3.1.3.4
2.7.1.107
NH2
+
+
H NCNHCH CH CH CH
2222 COO
(NH )
3
H
OH H
OH
CCCCO
OHH
HOCH2CH OH
2
R-CH2COO
CH O-CO-R
2
CH O-CO-R"
2
R’-CO-OCH
OH
O
CH CHNH
23
+
O
R
'
-CO-OCH
O-
CH O-CO-R
2
CH O PO
2
COO
OOCCH CH CH
22 COO
(NH )
3
+
CH CH(OH)CH(NH )COO
33
O
OH
HO
OH
OH
CH OH
2
CH OH
2
NH
CH O-CO-R
2
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,
theTCA CYCLE (mainly) in the Mitochondrial matrix
and ATP FORMATION spanning the
MITOCHONDRIAL INNER MEMBRANE
An electron flow (an electric current) generated from
NADH and UQH
2drives the translocation of protons
from the matrix to the intermembrane space.
Theretrolocation of these protons through the F0 subunits
ofAT P synthase to the matrix then supplies the energy
needed to form ATP from ADP and phosphate
Electron FlowProton 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
AT P
TR
A
N
S
L
O
C
A
T
E
D
PROTONS
2.7.1.1
AT P
2.7.1.2
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Metabolic Pathways

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2H+

H+

OXALOACETATE

PYRUVATE

SUCCINYL-CoA

GLUTARATE

CITRATE

MALATE

2-OXO- (^) ASPARTATE

NO 2 -

NO 3 -

N 2

NH 4

CH3COSCoA ACETYL-CoA

HOH

CO 2

NAD

T

RA

N

S A

MI

NAT

ION

2H+

2H

CO 2

5-Amino-

levulinate

Glycine

H+

H+

H+H+

H+

H+

c

a H+ H+

F 0

F 1

F 1

2 β

1 α

β α

(^10) c-sub-unit

s

A

D

P+Pi

a H+

H+

  • tra

nsport

i ngATPs ynth as e

α

δ F 6

oscp

ATP

ADP + Pi

FUMARATE

UQ H 2

UQ

UQ H 2

NADH+H+ CH2COO- C(OH)COO- CH2COO-

CH(OH)COO-

CHCOO-

CH2COO-

  • OOCCOCH2CH2COO-

-OOCCH2CH2CO.SCoA

- OOCCOCH2COO-

CH3CH(OH)CH 2 CO.SCoA

- OOCCH=CHCOO-

CCCC

Glyoxylate Cycle

- OOCCHO

GTP

ATP GDP

HEME Protoporphyrinogen Coproporphyrinogen Uroporphyrinogen Porphobilinogen

5-Amino-

levulinate

COO-

CH

CH

H2NCH2C=O

FAD H 2

Cyt.b FAD

Fe-S

SUCCINATE

II

CH3COCOO-

PYRUVATE

Pi

X Y

Cyt.c 1

Fe-S

2e-

2e-

1e-

1e-

III

2UQ UQ

2 UQ H 2 UQ H 2

2UQ.

_

UQ.

_

Cyt.b L Cyt.bH

Cyt.c

IV

Cu A

Cu B

Cu A

2e-

Heme a

Heme a 3

2H +

2H +

4H +

4H +

2H +

NAD+

NADH+H +

NAD+

-OOCCH2CH2COO-

ISOCITRATE

1.18.6.

δ^ ε

H++

(^33) β

AT

P

ADP

ENDER

GONICREACTION

I

FMNH

FMN I

2Fe -S

(5 Clusters)

H+ H+

H+ H+

ATP

4H + 2H +

2H +

or

H+

PHOTO-

SYSTEM

l

O 2

NADP+

Glyceraldehyde Ribulose-1,5-bis-P

β 2

(^88)

c^ H+

3

a

3 2

1 α α

ε

α

1 2 β

3

α α

β

3

α

β

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

PQH 2

2PQH 2

PQ_.

2PQ_.

Fe-S (^) Cyt.f

PQ

2PQ

Cyt bf

2e-

1e- (^) 1e-

2e-

2e-

2e-

2e-

Cycl

icPhotop

hosphoryl ation

PQ

PHOTO- SYSTEMII

Cyt bc

Non

  • cyclicelectro

nflo

w

2e-^ 2e-

Mn^ 2e-


Protons from Water

H 2 O

H+

H+

2H +

2H +

ATP synthase

CO (^2) Fixation

H+

Pi ADP

H+

NADPH+H +

eee

THYLAKOID MEMBRANE ATP

CHLOROPLAST OUTER MEMBRANE

THYLAKOID LUMEN

STROMA

(electriccurren t)

P680Chl.a

QA

QB

Pheophytin

P

Chl.A (^0)

A 1

Fe-S

ATP

ADP

ATP

(^1) / 2 O 2

H 2 O

PQH 2

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

CO CH CH(NH )COO 2 + 3

FOLIC

ACID

C

POOL

VALINE

ATP

ATP

CH COCH 3 3

CH COCH COO 3 2

CH CH(OH)CH COO 3 2

Acetone 3-OH-Butyrate

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

CH 3 O

OOHOPPT

OH

O

OH

ACNH

HO OH

O

HO OH OPPU

NHAC

OH

OH OH

OH

HO

OH

NHCOCH

OH HO

O

OPPG

CH OH 2

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

Gulonate Glucuronate Inositol Inositol- P

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

HOCH 2 C C C C CO

H OH OH OH

H H

O

HOCH 2 C C C CO CO

HOH

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 OH 2

CH OH 2

HOCH

CH OH 2

CH O 2

HOCH

P

Glycerol

UDP-Galactose

UDP-Sugars

CH CH OH 3 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 CHO 2

Indolepyruvate

N H

C-CH(OH)CH(OH)CH 2 O P

CH

2-Aminomuconate-

6-semialdehyde

CH CH NH 2 2 2

NH

Dehydro-

quinate

Shikimate-3- P Shikimate-

enolpyruvate 3- P

Chorismate

PEP

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 )COOH 2 + 3

1.1.1.23 Histidinal^ Histidinol 3.1.3.15^ Histidinol- P 2.6.1.

Asparagine

ALANINE

3-Sulphinyl

pyruvate

Oxobutyrate

2-Aceto-2-

hydroxy-

butyrate

O-Phospho-

homoserine

HO SCH CH NH 2 2 2 2

Hypotaurine

HO SCH CH NH 3 2 2 2

Taurine

Glutamate

γ -Glutamylcysteine

Glutathione

Glycine

Cysteine

ß-Alanine

Cysteate homocysteineS-Adenosyl

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

2-Isopropyl-

malate

CH CH COCOO 3 2

CH CH(NH )COO+

3 3

CH CH(OH)COO 3

HO SCH COCOO 2 2

P OCH COCOO 2

P OCH CH(NH )COO 2 3

HOCH COCOO 2

HOCH CH(NH )COO 2 3

OH

CH COCOO 2

COO

OH

OOH

COO

OH

OH

HO P

COO

OH

O OH

CH 2

P

COO

O-C-COO

O OH OH

OOC CH COCOO 2

N H

HOC-CH(OH)CH(OH)CH 2 O P

CH

COO

NH 2

COO

OH COONH^2

COO

OCH

OOCCH NHCH 2 3

CH (CH ) 3 2 14 COS-ACP CH (CH ) 3 2 14 COSCoA

CH (CH ) CH=CHCO-S-ACP 3 2 2

CH CH=CHCO-S-ACP 3 CH CH(OH)CH COS-ACP 3 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

2, 3-Hexenoyl-ACP 3-OH-Hexanoyl-ACP 3-Oxo-Hexanoyl-ACP

Butanoyl-ACP Crotonoyl-ACP 3-OH-Butanoyl-ACP Acetoacetyl-ACP

Hexanoyl-ACP

Decanoyl-ACP 3-OH-Decanoyl-ACP

Palmitoleoyl-ACP

γ -Linolenate Arachidonate Leukotriene B

COSCoA

CO-S-ACP

Thromboxane B

HOOCCH CO-S-ACP 2

Malonyl-ACP

HOOCCH CO-SCoA 2

Malonyl-Co-A

CH CO-S-ACP 3

Acetyl-ACP

CH O-CO-R 2

CH OH 2

R’-CO-OCH

FATTY ACID ACYL-CoA

(Cytosol)

CH O-CO-R 2

CH O 2

R’-CO-OCH

P

Cardiolipin Phosphatidylglycerol

Acetylcholine

Glycerophosphocholine

Lysolecithin

Choline

plasmalogen

CDP-choline Choline- P

Mevaldate

CH (CH ) 3 2 12 CH=CHCH(OH)CHCH 2 OH

Dehydrosphinganin Sphinganin 4-Sphingenin Psychosine

Acyl-CoA

Acyl-CoA

Cerebroside

CH (CH ) 3 2 12 CH=CHCH(OH)CHCH 2 O- Galactose

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 O 3 2 PP

CH 3

Ceramide

Gangliosides

NHCOR

CH O 2 PP

O PP

CH 2

CHOLESTEROL

CH C(OH)CH CH OH 3 2 2

CH COO 2

CH C(OH)CH CHO 3 2

CH COO 2

NADP +

Dehydroascorbate

OH

H O

HOCH 2 C C C C CO

H OHOH

OH

H O

HOCH 2 C C CO CO CO

H

NAD+

Pi

ADP ADP

Phytoene

(C40)

Lycopene (C40)

ß-CAROTENE (C40)

Metarhodopsin Rhodopsin

Retinoate

trans -Retinal

trans -Retinol 11- cis -Retinol

(Vitamin A)

Retinol esters

Dark

Light

Ubiquinone

(Coenzyme Q)

Menaquinone

Plastoquinone

Phylloquinone

(Vitamin K)

Opsin

CHO

CH OH 2

CHO

CH OH 2

CH O 3 CH^3

CH O 3 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

HO CH CH NHCOCH 2 2 3

NH

CH O 3 CH CH NHCOCH 2 2 3

NAD( P )

NICOTINATE

N-Acetyl-serotonin

Dopamine Dopa

Dopaquinone

MELANIN THYROXINE

OH

OH

CHOHCH NHCH 2 3

OH

OH

CHOHCH NH 2 2

4-OH-3-Methoxy-

phenylglycol

CHOHCH NH 2 2

OHOCHOCH^3 3 CHOHCH OH 2

OH

OCH 3

4-OH-3-Methoxy-

D-mandelate

Cyclic AMP

ATP

Dephospho-Coenzyme A

4- P -Pantetheine

4- P -Pantothenylcysteine

4- P -Pantothenate

Pantoate

NH

HN

O

O

O

O

CH OH 2

OH

OCH 3

CH(OH)COO

H 2

NH 3

+ CH-COO

O C

O

COO

Ribose- P N

N+

COO

NH

CH COO 2

O

OH

CH O 2 P

NHCOCH NH 2 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 NCONH 2 2

HN

H C 2 CHO

NH R P

NH

C

CC

O

C

CO

OC NH

NH

HN

HN

H

CC

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

C CH

NH 2

OC CH

NH

CCH N

O

OC N CH

H

HN

CCH-CH 3

O

OC

NH

HN

CH 2

CH 2

CH 2

CO

OC

NH

HN

CO

OCCH

NH

HN C CH^3

Methylmalonyl

semialdehyde

OHCCHCOO

CH 3

CCH 2

O

OC CH-COO

N H

HN CH

OC

OC C-COO

N H

HN

H NCONHCH CH COO 2 2 2

CC

C CH

HC NHRP

NH

OOC-CH-CH COO 2

N

N

N

CHO

NH R P

NH

OC

H C 2

2.7.1.

5.1.3.

HOOC-COOH

Oxalate

Glycolate

HOCH CHO 2

Glycol

aldehyde

Ethanolamine- P

4.1.3.

3.1.1.5 3.1.4.

2.7.8.

2.4.1.

1.4.1.

ACETATE

2.4.2.

R P

C CH

O

OC CH

N

HN

2.7.7.

LACTATE

Acetaldehyde

Bile Acids

CH CH COSCoA 3 2

Propanoyl-CoA

CDP-Ethanolamine

HO SCH CH(NH )COO 2 2 3

HN NH

CH

OOC CHCH CH COO 2 2

CMP-N-Acetyl

neuraminate

CDP-diacyl

glycerol

CHOLINE

Ethanolamine

Glyoxylate

HISTAMINE

Homoserine 2.3.1.

Tyramine

TanninsPlant Pigments

Maleyl

acetoacetate

Fumaryl

acetoacetate

CH COO 2

OH

OH

OH

CH CH NH 2 2 2

OH

OH

CH CH NH 2 2 2

Hydroxyphenyl

pyruvate

α -Tocopherol

(Vitamin E)

LIGNIN

d-GTP

OH

OH OH

O

HO

OH

P

OPPT

HOCH 3

OHOH

O

NADPH

ATP

CH CH NH 2 2 2

NH

HO

Indole

OHO OH

NH C C CH CH O 2 P

COO H H

NH 2

COO

Guanine

DNA

CC

O

HC C^ NHCH

N

N

HN CC

O

HC C^ NHCH

N

N

HN

2.4.2.

2.7.7.6 2.7.7. 2.7.7.

Diphospho-

mevalonate

Mevalonate

3-Oxopentanoyl-CoA

2, 3-Enoyl-CoA 3-OH-Acyl-CoA 3-Oxoacyl-CoA

2, 3-Hexenoyl-CoA 3-OH-Hexanoyl-CoA

Crotonoyl-CoA 3-OH-Butanoyl-CoA Acetoacetyl-CoA

Pentanoyl-CoA 3-OH-Pentanoyl-CoA

Odd C Fatty acids

Succinylhomoserine

CO 2

2-OXO ACID

Glutamyl- P

Glutamine

UREA

Creatine P -Creatine Creatinine

Glycine

CITRULLINE

Glutamic

semialdehyde

2-AMINO ACID

Pyrroline-5-

carboxylate

PyruvateGlyoxylate

4-Hydroxy-

2-oxoglutarate

4-Hydroxy-

glutamate

3-Hydroxy-

pyrroline-

5-carboxylate

Putrescine

H NCH CH CH CH NH 2 2 2 2 2 2

Spermidine

Spermine

N -Trimethyl-^6 N -Trimethyllysine^6

3-OH-lysine

Carnitine

Glutaryl-CoA 2-Aminoadipate Saccharopine

semialdehyde

2-Oxoadipate 2-Aminoadipate

Arginino-

succinate

Guanidoacetate

Methylmalonyl-CoA

Aspartyl

Semialdehyde

2, 3-Dihydro-

dipicolinate

1.2.1.

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-Methyl-

glutaconyl-CoA

(CH ) CHCH COSCoA(CH ) CHCH COSCoA3 23 2 22

3-Methyl-

crotonyl-CoA

Isovaleryl-CoA

HCHO Oxopantoate

OOCCH C = CHCOSCoA 2

CH 3

CH COCHCOSCoA 3

CH 3

CH CH=CHCOSCoA 3

CH 3

CH CH(OH)CHCOSCoA 3

CH 3

C(OH)CH(OH)COO

CH CH 3 2

CH 3

CH 2 = CCOSCoA

CH 3

HOCH CHCOS-CoA- 2

CH 3

CH CHCO-SCoA 3

CH 3

C (OH)CH(OH)COO

CH 3

CH 3

CH CH CHCOSCoA 3 2

CH 3

CH C = CHCOSCoA 3

CH 3

ATP

4-Aminobutyrate

(GABA)

1.1.1.85 Oxoleucine

COOH

(CH ) CHCHCH(OH)COO3 2

S-Adenosylmethyl

thiopropylamine

(Decarboxylated SAM)

PROLINE

Coenzyme A

CH C= CHCH 3 2

CH 3

O

CH

CH

3

HO 3

CHCH 3 3

CH 3

CH C-CH 3 2 CH O 2 PP

CH 2

CH C= CHCH O 2 2 PP

CH 3

3- P -Glycerol

Phosphatidyl

ethanolamine

CEPHALIN

Progesterone

4.4.1.

Acetylserine 1.8.99.1 2.7.1.25 Adenylylsulphate(APS) 2.7.7.

4.2.99.

P-Ribosyl- PP

Aspartyl- P

4.1.3.

CHOLINE

P OCH C(CH ) CH(OH)CO 2 3 2 NHCH CH CO 2 2 NHCH CH SH 2 2

ADP- OCH C(CH ) CH(OH)CO 2 3 2 NHCH CH CO 2 2 NHCH CH SH 2 2

P -ADP- OCH C(CH ) CH(OH)CO 2 3 2 NHCH CH CO 2 2 NHCH CH SH 2 2

CH CO-OCH CH(NH )COO+

2 2 3

Glyoxylate

Hexanoyl-CoA

Butanoyl-CoA

NO

SO

OOC NH 2

OOC

1.3.1.

CYTIDINE-

triphosphate

(CTP)

Cytosine

HSO 3

NADPH

2.3.1.

O

OPPU

CH OH 2

CH OH 2

HO OH

OH

HO

4.2.1.

O

CCH

OC CH

N

HN

D P

C CH

O

OC NCH

HN

R PPP

OCH 2

H

C C

H

OHOH

CH

HN N

CH

P C

H

O

OCH 2 C C

H

OH

H

OH

C

H

C CC

NH 2

C

CH

HC N

R P(PP)

N

N

P N+

H^ NH^2

O

OCH 2 C C

H

OH

H

OH

C

H

C C

OC

C

CH

HC N

R P

N

N

P NH

H

OCH 2 C C

H

OHOH

CO CH 2 C

CONH 2

C

CH

HC N

RP

N

N

P NH

OOCCH N(CH )^ +

2 3 3

Betaine

Betaine

aldehyde

O

OH

CH OH 2

HO

HO O P

ß-OH-ß-Methyl-

glutaryl-CoA

C

C

O

OC C^ N RCH

P

N

N H

HN

CC

O

C

CH

N

N

N

HN

H N 2 C R P

Carbamoyl- P

Carnitine

2.6.1.4^ 2.6.1.

CH C(OH)CH COSCoA 3 2

CH COO 2

Menaquinone

Carnosine

C CH CH NH 2 2 2

N CNH

HC

H

Ubiquinone

Plastoquinone

D-Ribose-5- P

NH

HO CH CH(NH )COO 2 3

O

OH

OH

HO

OPPU

COO -

O

OH

OH

HO OPPU

COO -

OH

H OH

HOCH 2 C C CO

H

CO COO -

CHOHO

AcNHCHOH

HO

OPC

COO -

CH OH 2

CHOHO

AcNHCHOH

HO

OH

COO

CH OH 2

O

HOOH HOOH

CH O 2 P

O

OH

HO ACNH

OH

CH O 2 P

O

HO OH HOO P

CH OH 2

O

HOOH HOOH

CH OH 2

O

HO OHOH

3

CH O 2 P

O

HO OHO

NHCOCH 3

P

CH OH 2 CH OH 2 CH OH 2

O

HO OH OH

NH 2

CH O 2 P

O

OH

HO

OH

OPPU

CH OH 2

O

O

HO

OH

OH

HO

P

CH OH 2

CH OH 2

O

O

HO

OH

OH

O

OH OH

OH

CH OH 2

O

HOOH

OH

OH

CHCH O 22 P

OH

H OHH H

C C C C

HOH OH

HOCH 2 COO -

H

OH OHOH

C C C CHO

HH

HOCH 2

H

OH HOH

C C C CHO

OHH

HOCH 2

OH

H HOH

C C C CHO

OHH

HOCH 2

H

OH OHH

C C C CHO

HOH

HOCH 2

OH

H OHH

C C C CHO

HOH

HOCH 2

OH

H OHOH

C C C CHO

HH

HOCH 2

H

OH OHH

C C C C

H OHH

OH

P OCH 2 COO -

OH

H OH

C C CO

H

P OCH 2 CH OH 2

H

OH H

C C CO

OH

HOCH 2 CH OH 2

P OCH 2 CH OH 2

H

OH OH

C C CO

H

P OCH 2 CH OH 2

OH

H H

C C CO

OH

P OCH 2 CH OH 2

H

OH OH

C C CO

H

HOCH 2 CH OH 2

OH

H OH

C C CO

H

HOCH 2 CH OH 2

OH

H H

C C CO

OH

HOCH 2 CH OH 2

H

OH HOH

C C C

OHH

HOCH 2 CH OH 2

OH

H OHOH

C C C

HH

HOCH 2 CH OH 2

H

OH OHH

C C C C

H OHH

OH

HOCH 2 CH OH 2

H

OH OH

C C CHO

H

P OCH 2

H

OH OHH

C C C CO

HOH

HOCH 2 CH O 2 P

H

OH OHOH

C C C

HH HOCH 2 CH OH 2

H

OH OH

C C C

H

CO

H

HO

P OCH 2 CH OH 2

P

H

OH OH

C C C

H

CO

H

HO

OCH 2 CH O 2 P

H

OH OH

C C

H

C CHO

OH

H

PP OCHOCH 2

O

OH

NH 2

OH

CH O 2 P

P OCH^ CHOHCHO 2

HOCH 2 COCH 2 O P

O

OH

O P O P

OH

CH O 2 P

P OCH 2 CHOHCOO P

P OCH 2 CHOH COO

COO

OH

HO O

OH

COO

CH (CH )CH (CH ) 33 2 142 14 CH(OH)CH COS-CoA CH(OH)CH COS 22

CH (CH ) 3 2 14 COCH COS-CoA 2

CH (CH ) 3 2 14 COCH COS-CoA 2

CH (CH ) 3 2 n+ 2 COS-CoA

CH (CH ) 3 2 14 CH=CHCOS-CoA

CH (CH ) 3 2 n CH=CHCOS-CoA

CH (CH ) 3 2 5 CH=CHCH COSACP 2

CH (CH ) 3 2 6 CH=CHCOSACP

CH (CH ) 3 2 6 CH CH COSACP 2 2 CH (CH ) 3 2 6 COCH COSACP 2

CH (CH ) 3 2 2 CH CH COSACP 2 2

CH CH CH COSACP 3 2 2

CH (CH ) 3 2 6 CH(OH)CH COSACP 2

CH CH=CHCO.S-ACP 3

CH (CH ) 3 2 2 COCH COSACP 2

CH 3 COCH COSACP 2

CH (CH ) 3 2 n CH(OH)CH COSACP 2 CH (CH ) 3 2 n COCH COSACP 2

CH (CH ) 3 2 2 CH(OH)CH COSACP 2

ACYL-CoA

(Mitochondria)

CH (CH ) CH CH COSCoA 3 2 n 2 2 CH (CH ) CH=CHCOSCoA 3 2 n CH (CH 3 n CH(OH)CH COSCoA 2

CH (CH ) CH CH COSCoA 3 2 2 2 2 CH (CH ) CH=CHCOSCoA 3 2 2

CH (CH ) COCH COSCoA 3 2 n 2

CH COCH COSCoA 3 2

CH (CH ) CH(OH)CH COSCoA 3 2 2 2

CH CH CH COSCoA 3 2 2 CH CH=CHCOSCoA 3 CH CH(OH)CH COSCoA 3 2

CH CH CH CH COSCoA 3 2 2 2

Pentenoyl-CoA

CH CH CH=CHCOSCoA 3 2 CH CH CH(OH)CH COSCoA 3 2 2

CH (CH ) COCH COSCoA 3 2 2 2

CH CH COCH COSCoA 3 2 2

OH OH

HO OH

O

O -

CH O-PO 2

CH CHOHCH OH 2 2

O

CH 2

CH 2

R'-CO-OCH

O-CO-R

O-PO

O -

HOCH CH 2 2 NH+ 3

CPP- OCH CH 2 2 NH+ 3 P OCH CH 2 2 NH+ 3

O

CH O-CO-R 2

CH O P 2 OCH CH 2 2 NH+ 3

CH COCH CH N(CH ) 3 2 2 3 3

HOCH CH N(CH ) 2 2 3 3

CH CH 2 (NH )+ 3 COO

OH

OH

CH CH 2 (NH )+ 3 COO-

CO

NH 2

CH CH(NH )COO 2 + 3

OC NH

CO

OC N NH

H

CH

H N 2

HC CH

N

N

C

R P

H N 2

CCH

OC NCH

N

D P

NH 2

R PPP

C CH

OC NCH

N

NH 2

CC

HC C NCHR P(P)

N

N

N

NH 2

H NCOO 2 P

H N(CH ) NH 2 2 3 (CH ) NH2 4 (CH ) NH2 3 2

H N(CH ) NH 2 2 4(CH ) NH2 3 2

CH -SCH CH CHNH 3 2 2 2

Adenosyl

CH 3 +

CH 3

CHCH(NH )COO 3

C ++

NNH

C

HC

H

CH CH(NH )CH OH 2 3 2 C +

NNH

C

HC

H

CH CH(NH )CH O 2 3 2 P C

NCNH

H

HC CH COCH O 2 2 P

HSCH CH CH(NH )COO+

2 2 3

SCH CH CH(NH )COO+

2 2 3

CH CH(NH )COO 2 3

R P

C

O

OC C-COO

N

HN CH

CH (CH ) 3 2 12 CH=CHCH(OH)CHCH 2 OH

NH+ 3

CH (CH ) 3 2 14 CH(OH)CHCH OH 2

NH 3

CH (CH ) 3 2 14 COCHCH OH 2

NH 3

CH (CH ) 3 2 12 CH=CHCH(OH)CHCH 2 O- Galactose

NH+ 3

H NCONH 2 2

OHCCH N(CH ) 2 3 3

CC-CH 3

O

OC CH

N D P

HN

D P

C PP -OCH CH N(CH ) 2 2 +^ 3 3 OCH CH N(CH ) 2 2 +3 3

UDP-N-Ac-Muramate

O

O

CH CH 3

COO-

NHAC

HO OPPU

CH OH 2

O

OH

CH 3

HO HO OPPG

5.3.1.

Sedoheptulose- PP

N

CH 2

CH 2

N

N

N

CH 3

CH 3

CH

CH

COO

CH CH

CH 2

H C 3

H CH C 33

HC

C

C

H

H

Fe

CH 2

CH 2

COO-^ -

CH 3

CH 3

CH 2

CH 2

CH 2

H C 3

H C 3

NH

NH

HN

HN

CH

CH

H C 2

C

CH^2

H 2

CH 2

CH 2

COO

CH 2

CH 2

COO -

H C 2 H C 2

CH 2

CH 2

OOC

COO

H N 2

NH

CH 2

H C 2

H C 2

H C 2

H 2

H 2

CH 2

CH 2 CH 2

CH 2

CH 2

CH 2

NH

NH

HN

HN

COO

COO

COO

COO

C

C

CH 2

CH 2

COO

CH 2

CH 2

COO-^ -

- OOC

- OOC

CH 3

CH 3

H C 3

H C 3

H C 2

H 2

H 2

NH

NH

HN

HN

CH 2

CH 2

CH 2

CH 2

CH 2

C

C

COO-

CH 2

CH 2

COO

CH 2

CH 2

- COO-

COO-

COO-

CH C(OH)CH CH O 3 2 2 PP

CH COO 2

OHCCOO

HOCH COO 2

NH 2

H NCNHCH COO 2 2

+ NH 2

H NCN(CH )CH COO 2 3 2

+ NH 2

P- HNCN(CH )CH COO 3 2

+ HN C NH^ CO

N CH 2

CH 3

OOCCHCH 2 COO

H NCNHCH CH CH CH 2 2 2 2

N

(NH )+ 3 COO

HCCHCOO

HOCHCH 2

N

OOCCH(OH)CH 2 CH(NH )COO + 3

CHCOO

HOCHCH 2

H C 2

NH

NH

CHCOO

CH 2 CH 2

CH 2

OOCCH(OH)CH 2 COCOO

N

CHCOO

CH 2 CH 2

CH

CH COCOO 3 OHCCOO

H NCONHCH CH CH CH+

2 2 2 2 (NH ) 3 COO

H NOCCH CH CH 2 2 2 (NH )+ 3 COO

R-CO-COO

R-CH(NH )+ 3 COO

H NOCCH CH 2 2 (NH+ 3 COO

OOC-CH-COSCoA

CH 3

P OOCCH CH 2 (NH )+ 3 COO

OOCCH CH CHO 2 2

OHCCH CH 2 (NH )+ 3 COO

(CH ) NCH CH(OH)CH COO3 3 2 2

OHCCH CH CH 2 2

(NH ) 3 COO

P OOCCH CH CH 2 2 (NH )+^3 COO

OHCCH CH CH CH 2 2 2 (NH )+^3 COO

NH CHCH CH COO 2 2

COO

CH CH CH CH CH 2 2 2 2 (NH ) 3 COO

(CH ) N(CH )3 3 +^ 2 3 CH CH(NH )COO 2 + 3 H N(CH ) 2 2 4 CH(NH )COOCH(NH++ 3 3

CCH 2

H

OOCC N

HC

CH-COO

CCH 2

H 2

OOCC NCH-COO

H C 2

OOCCOCH CH CH CH-COO 22 CH CH 22 22

OOCCH CH CONH 2 2 OOCCHCH CH CH CH-COO 2 2 2

OOCCH CH CONH 22 CH 22

NH 3

+ OOCCH-CH CH CH CHCOO^2 2

NH 3

NH+ 3

(CH ) CHC(OH)CH3 2 2

COOH

COO (CH ) CHCH COCOO3 2 2

(CH ) CHCH +

3 2 2 CH(NH )COO 3

HOCH CHCOO 2

CH 3

CHCOCOO

CH 3

CH COC(OH)CH 3 3 CH^3

COO

P OCH CH CH(NH )COO 2 2 3 HOCH CH CH(NH )COO 2 2 + 3

CH CH CH(NH )COO+

OOCCH CH 2 2 COO 2 2 3

+ CH SH^2

OOCCH(NH 3 )CH CH CONHCHCONHCH 2 2 2 COO

HOCH 2 C(CH ) COCOO 3 2

HOCH 2 C(CH ) CH(OH)COO 3 2

HOCH C(CH ) CH(OH)CO 2 3 23 2) NHCH 2 CH COO 2

P OCH C(CH ) CH(OH)CO 2 3 2 NHCH CH COO 2 2

CH CH 3 2

CH 3

CH CH(NH )COO+ 3

CH COC(OH)CH CH 3 2 3

COO CHCOCOO

CH CH 3 2

CH 3

NHCHCH SH 2

COO

P OCH C(CH ) CH(OH)CO 2 3 2 NHCH 2 CH CO 2

OOCCH(NH^ +^ )CH CH CONHCHCOOCH SH^2

3 2 2

AdenosylSCH CH CH(NH )COO+ 2 2 3

SCH CH CH(NH )COO+

2 2 3

HO SCH CH(NH )COO+

3 2 3

S-CH CH(NH )COO 2 + 3

S-CH CH(NH )COO 2 3

HSCH CH(NH )COO+

2 3

H

C

NCNH

HC CH CHCOO 2

NHCOCH CH NH 2 2 2

H

C

NNH

C

HC CH CH(NH )COO 2 3

CHCH CH COO 2 2

N NH

CH

OC C CH CHCOO

N NH

CH

CH

CH COO 3

NH

OOC

OCCH-COO

NH 2 CH 2

H NCH CH COO 2 2 2

H NCH 2 2

CH 3

CHCOO H NCONHCH CHCOO 2 2

CH 3

CC

O

CH

HC NR P

N

N

HN

C

CC

O

HCO CH

N

N

N R P

C

CH

N

H N N

2 H C

CC

O

CH

N

CCN

CH

N

N

R P

H N 2

H N 2 C

O

O

O P~^ P~ O

O

O O

P O

O

CH 2

N

N

N

N

O

OHOH

NH 2

HC

N CH

N

N

N

O

O

P O O

O

CH 2

OH

NH 2

HC

CH

COOCO

OC NHCHNH

H N 2 NH^2

OOC-CH-CH COO 2

HNCO C CH

N

N

C

RR PP

H N 2

OOC

C CH

N R P

N

C

H N 2

CH=CHCOO

OH

CH=CHCOO

CH COCOO 2

CH 2

P

COO

OOH

O

O

COO

O

-OOC OCH COO 2 CH COO 2

OCH 2 CH 2

HCOH

P

HOCH HCOH

OC

COO

HOCOO

OH

OOH

OCHCOONH 2

NH

CH COCOO 2

NH

CHO

CO

NH 2

OH

CH CH(NH )COO 2 + 3

N

COO

COO

N+

COO

COO

R P

O

OH

OH

HO OPPU

COO

O

OH

NHCOCH 3

HO

OPPU

COO

CH OH 2

O

O

CH 2 C NHAC

HO OPPU

COO

CH OH 2

O

HO OHOH

OH

COO

OOCCH N(CH ) 2 3 2

Dimethylglycine

COO

HO HO COO

O

HO OH

COO

P OCH 2 CH(O P )COO HOCHCH(OH)

2 COOCOO

HOCH 2 CH(O P )COO

CH =C(O 2 P )COO

CONH 2

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

I I

I I

OH

O

Epinephrine CH CH 2 (NH )+ 3 COO

(Adrenaline)

Norepinephrine

(Noradrenaline)

Normetepinephrine

(Normetadrenaline)

HOCH CH N (CH ) 2 2 +3 3

Adenosyl

+SCH CH CH(NH )COO^2 2

CH 3

(CH ) N(CH )3 3 +^ 2 3 CH CH(NH )COO 2 + 3

OH

OOCCH 2 CH CH COSCoA 2 2

OOCCH CH CH NH 2 2 2 2

OOCCH 2 CH CH COCOO 2 2 OOCCH 2 CH CH CH 2 2 (NH ) 3 COOCOO

HO

H

HO

H

HO H H

HO

H

Prostaglandin PGE 2

OH

HOCH 2 C C CO C COO

H OH

H OH H

COO

R'-CO-OCHO

CH O-CO-R 2

CH O POCMP 2

O

CH CH N(CH ) 2 2 + 3

HOCHO

CH OPO 2

CH OH 2

O -

CH OPO 2

O

CH OCH=CHR 2

CH CH N(CH ) 2 2 +3 3

O-

CH OPO 2

R'-CO-OCHO

CH 2 O-CO-R

CH CH N(CH ) 2 2 +3 3

O-

HOCHO

CH OPO 2

CH O-CO-R 2

CH CH N(CH ) 2 2 +3 3

O-

CH CH(NH )COO 2 + 3

C +

NNH

C

HC

H

CH CH(NH )CHO 2 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

Diacyl

glycerol

CH CHO 3

OHCCH 2 COO-

etc.

ADP

P -Glucono

lactone

O

O

HOOH

OH

CH O 2 P

TYROSINE PHENYLALANINE

TRYPTOPHAN

INOSINE- P

(IMP)

THYMIDINE- P

HISTIDINE

URIDINE-

triphosphate

(UTP)

CYSTINE CYSTEINE

ISOLEUCINE

LEUCINE

LYSINE

ORNITHINE

ARGININE

HYDROXY PROLINE

PHOSPHATIDYL

Phosphatidyl SERINE

inositol

LECITHIN

SPHINGOMYELIN

STEROIDS

Pregnenolone

H

OH OH

C C C

H

CO

OH

C

H

H

OH

P OCH 2 CH O 2 P

ADP

Endoplasmic Reticulum

Phosphatidate

PO

O

CH (CH ) 3 2 12 CH=CHCH(OH)CHCH 2 O

NHAcyl CH CH N(CH ) 2 2 +3 3

O-

METHIONINE

Glycinamide-

ribosyl- P

3-Oxohexanoyl-CoA

THREONINE

GLUTAMATE

ATP

NADH

SUCROSE

ADENOSINE- P

(AMP)

Triacylglycerol

FAT

RNA

CH 3

CH 2

OHOC-COO

COO

CH CH 2 (NH )+ 3 COO

GLYCOPROTEINS

GANGLIOSIDES

MUCINS

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 2 2 O-P-OCH 2

CH O-CO-R’ 2

R '-CO-OCHO

O -

CH O-CO-R 2

CH O-PO 2

O -

H NCH CH CH CH 2 2 2 2 (NH ) 3 COO

NH 2

H NCNHCH CH CH CH 2 2 2 2 (NH ) 3 COO

H

OH OHH

C C C CO

HOH

HOCH 2 CH OH 2

R-CH 2 COO

CH O-CO-R 2

CH O-CO-R" 2

R’-CO-OCH

OH

O

CH CHNH 2 + 3

R' -CO-OCHO

O -

CH O-CO-R 2

CH O PO 2

COO

OOCCH CH CH 2 2 (NH ) 3 COO

CH CH(OH)CH(NH )COO+

3 3

O

HOOH

OH

OH

CH OHCH OH 22

NH

CH O-CO-R 2

Malonic

semi-

aldehyde

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

TR

A

N

SL

O

CA

TED

PROTONS

ATP 2.7.1.

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Molecular Biology www.iubmb.org

22

nd Edition Designed by Donald E. Nicholson, D.Sc.,

The University of Leeds, England – and Sigma-Aldrich Cat. No. M

XXX

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Metabolic Pathways