Metabolic Pathways

BLOOD GROUP ALGINATES O-ANTIGENS

HYALURONIC ACID
DERMATAN
STARCH
SUBSTANCES
PEPTIDOCHONDROITIN
PECTIN
INULIN
CELLULOSE
GLYCAN CH OHCHITIN

COO -

O
COO -

6.3.2.7-10
6.3.2.13 HO O

2.4.99.7

CH2OH

OPC

OPPU

CH3CH

NHAC

O
CHOH
CHOH
CH2OH
HO

HO

1.1.1.158

3.1.3.29

N-Ac-Neuraminate

CH2OH
O

HO O
CH2 C

(Sialate)

COO

CH2OH
O

HO

HO OH

2.7.1.7

Mannose-1-P

HO OH

OPPU

UDP-N-Ac-Glucosamine
COO

HOCH 2

OH H

OH OH

OH H

COO -

C
H

HOCH 2

OH

OH

CO

OH H

HOCH 2 C

OH

HOCH 2

OH

OH H

OH

CHO

OH H

L-Xylose
OH H

HOCH 2 C

HOCH 2 C
H

CH2OH

CHO

OH

1.1.1.10

L-Arabinose

OH H

H
C

OH

2.7.1.47

HOCH 2

OH

OH H

CO

HOCH 2

C
H

HOCH 2
CO CH OH
2

PQ

1e-

P700

PC

OH

POCH 2

4.1.2.-

POCH 2 C
POCH

CHO

POCH2

HO

H OH

P-Ribosyl
amine

C CO CH2OP

Pi

Dihydroxyacetone-P

POCH 2CHOHCOOP

ADP
HO

COO

L
I
P
I
D

COSCoA

Oleoyl-CoA

1.14.99.5

CH3(CH2)14COS-ACP

CH 3(CH2)2CH 2CH2COSACP

3-Enoyl-ACP

Hexanoyl-ACP

4.2.1.

.60

4.2.1

CH3(CH2)2CH=CHCO-S-ACP

2, 3-Hexenoyl-ACP
CH3CH=CHCO-S-ACP

1.3.1.9

Butanoyl-ACP

Crotonoyl-ACP

CH3(CH2)n+2COS-CoA

6.2.1.3

FATTY ACID

3.1.2.20

2.3.1.15

Carnitine
O-Acyl-carnitine

L
I
P
I
D

CH2O-CO-R"

Triacylglycerol

2.3.1.20 glycerol 3.1.3.4 2.7.1.107

ACYL-CoA

1.3.99.3

(Mitochondria)

CH3(CH2)2CH2CH2COSCoA

Hexanoyl-CoA
CH3CH2CH2COSCoA

CH3(CH2)2CH=CHCOSCoA

4.2.1.17

CH3CH=CHCOSCoA

4.2.1.55

2, 3-Hexenoyl-CoA

1.3.99.2

Butanoyl-CoA

4.2.1.17

2, 3-Enoyl-CoA

1.3.99.3

Crotonoyl-CoA

3-OH-Hexanoyl-CoA
CH3CH(OH)CH 2COSCoA

CH 3CH2CH 2CH2COSCoA

CH3CH2CH=CHCOSCoA

CH3CH2CH(OH)CH 2COSCoA

Pentenoyl-CoA

Pentanoyl-CoA

OH

R'-CO-OCH

COO
O
+
CH 2O PO CH 2CHNH 3

PHOSPHATIDYL
SERINE
O

2.7.8.8

Phosphatidyl
ethanolamine
CEPHALIN
O

+
POCH2CH2 NH3

2.7.7.14

CDP-Ethanolamine

LECITHIN

.3
2.7.8

+
NH 3
CH3(CH2)12CH=CHCH(OH)CHCH 2OH

UDP-Sugars Acyl-CoA

Ceramide

3.1.4.12

Geranyl-PP

CH3

trans-Retinal

(C20)

Ubiquinone

2.5.1.10

(Coenzyme Q)
5.2.1.3

Light

1.1.1.105

11-cis-Retinal

Phytol (C20)

Plastoquinone

CH2OH

11-cis-Retinol

Dark

(Vitamin A)

CH 3

CH2OH

5.2.1.7

trans-Retinol

HO

O
CH3

(Vitamin K)

(C15)

CH

CH2

CH

H2 C

C
H

CH2
COO-

HEME

CH3

CH

N
H

N
H

H
N

H
N

H3 C

C
H2

CH2
H3 C

CH2

N
H

N
H

H
N

H
N

H3 C

C
H2

CH2

CH2

CH2

CH2

CH2

CH2

COO-

COO-

CH2

CH2

COO-

COO-

4.99.1.1

Protoporphyrinogen

1.3.3.3

CH2

Coproporphyrinogen

N
H

N
H

H
N

H
N

H 2C

OOC

CH2

C
H2

Brazil
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Tel: (+420) 246 003 200
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CH2

COO-

COO-

4.1.1.37

Uroporphyrinogen

Denmark
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Tel: (+45) 43 56 59 00
Fax: (+45) 43 56 59 05
Finland
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Tel: (+33) 474 82 28 00
Fax: (+33) 474 95 68 08

4.3.1.8
4.2.1.75

CH 2
CH 2

H2 C
H2 C

CH2

2003 International Union of Biochemistry and

Molecular Biology www.iubmb.org
Belgium
SIGMA-ALDRICH NV/S.A.
Free Tel: 0800 14747
Free Fax: 0800 14745
Tel: (+32) 3 899 13 01
Fax: (+32) 3 899 13 11

5-Amino-

-OOC

CH2

COO-

H2 O

COOlevulinate

CH2

CH2

(C30)

CH2
H2NCH2C=O

CH2
CH2

H 2C

CH3

CH2

CH2 H
2
C

H 2C

CH2

CH2

1.3.3.4

-OOC

Squalene

ADP +

IV

1/ O
2 2

COOCH2

COOCOO-

CH2

CH2

CH2
COO-

Lanosterol

5.4.99.7
1.14.99.7

COOCOOCH3

H2
C

H2 C

CH3

Zymosterol

CH2
CH3 CH
2

H2
C

H3 C

Pi

AT
E

H+
H+
H+

H+
H+

Porphobilinogen

CH3

OOCCH 2C = CHCOSCoA

HC
OOCC

H
C

H+

H+

N2

ADP Pi

ATP

2.7.1.33
P OCH 2C(CH 3)2CH(OH)CONHCH 2CH2COO

4-P-Pantothenate
Cysteine
6.3.2.5

COO
P OCH 2C(CH 3)2CH(OH)CONHCH 2CH 2CO NHCHCH 2SH

4-P-Pantothenylcysteine

1.2.1.25

CH3CH 2CHCOSCoA

4.1.1.36
P OCH 2C(CH 3)2CH(OH)CONHCH 2CH 2CO NHCH 2CH 2SH

4-P-Pantetheine

RGONIC REACTIO N

1.4.1.9

OOCCH 2CH2CH2COCOO

2-Oxoadipate

2.7.2.

NH2

CH

2.6.1.13

Guanidoacetate

Creatine

CH3COCOO

+ NH2

OHCCOO

4.1.3.16
OOCCH(OH)CH 2COCOO

CH2
CHCOO

1.14.11.2
HOCH

4-Hydroxy2-oxoglutarate

Biosynthesis
Degradation

4-Hydroxyglutamate

N
H

NH

N
CH3

CO
CH 2

Degradation

Biosynthesis

Photosynthesis Dark Reactions

Human Metabolism is identified as far possible by black arrows

1.5.1.12

Degradation

Biosynthesis

COMPARTMENTATION

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

CHCOO

HYDROXY
PROLINE
HN C

Biosynthesis
Degradation

Vitamins Co-enzymes & Hormones

2.6.1.23

CH2

H2C

P- HNCN(CH 3)CH2COO

3.5.2.10

Purines &
Pyrimidines

Pentose Phosphate Pathway

PROLINE

Argininosuccinate

P-Creatine

Lipids

Pyruvate Glyoxylate

CH2

OOCCHCH 2COO
N
+
H2NCNHCH 2CH 2CH2CH(NH3) COO

2.7.3.2

Amino Acids

Biosynthesis
Degradation

NH

H2NCN(CH 3)CH2COO

LEGEND

CHCOO

1.5.99.8
CH2
1.5.1.2

4.3.2.1

2.1.1.2

Saccharopine

Carbohydrates
Biosynthesis
Degradation

Pyrroline-5carboxylate

6.3.4.5

+ NH2

+
CH 2CH2CH2CH2CH (NH3) COO

S-Adenosylmethyl
thiopropylamine

ARGININE
H2NCNHCH 2COO

A
C
I
D
S

CH3-SCH 2CH2CHNH 2

2.5.1.16

2.1.3.3

NO

A
M
I
N
O

COO
NH CHCH 2CH2COO

1.5.1.9

Putrescine

Glutamic
semialdehyde

1.14.13.39

LYSINE

+
OHCCH 2CH2CH2CH (NH3) COO

2-Aminoadipate 1.2.1.31 2-Aminoadipate

2.6.1.39
semialdehyde

H2NCH2CH2CH2CH2NH2

+
OHCCH 2CH 2CH(NH3) COO

4.1.1.17

3.5.3.6

N6-Trimethyllysine

+
OOCCH 2CH2CH2CH (NH3) COO

.7
5.1.1
20
4.1.1.
1.5.1.7 - 10

+
H2N(CH 2)4 CH(NH 3)COO

+
+
(CH3)3N(CH 2)3 CH2CH(NH 3)COO

1.14.11.8

Spermidine

1.2.1.41

+
H 2NCONHCH 2CH2CH2CH(NH3) COO

3.5.3.1

+
NH3
OOCCH-CH 2CH2CH2CHCOO
+
NH 3

OOCCHCH 2CH2CH 2CH-COO

+
NH3

N-Succinyl- 2.6.1.17 N-Succinyl-2, 6 3.5.1.18 Diamino2-amino-6-oxodiaminopimelate

pimelate
pimelate

H2N(CH 2)4NH (CH2)3NH2

CH2 CH2

+
H2NCNHCH 2CH2CH2CH (NH3) COO

Coenzyme A

OOCCH 2CH2CONH
OOCCH 2CH2CONH
OOCCOCH 2CH2CH2CH-COO

2.5.1.22

6.3.5.5

UREA

2.7.1.24
P-ADP- OCH 2 C(CH 3)2CH(OH)CONHCH 2CH 2CO NHCH 2CH2SH

(CH3)2CHCH 2COSCoA

Isovaleryl-CoA

Adenosyl

11 POOCCH CH CH(NH ) COO

3
2
2

H2NCONH 2

2.1.4.1

Dephospho-Coenzyme A

(Decarboxylated SAM)

Glutamine

H2NCOOP

ADP- OCH2 C(CH 3)2CH(OH)CONHCH 2CH2CO NHCH 2CH2SH

LEUCINE
1.2.1.25

CH2
CH-COO

N6-Trimethyl3-OH-lysine

Spermine

+
H2NOCCH 2CH2CH (NH3) COO

ATP
CO2

Glycine +

+ NH

H2
C

2.7.7.3

+
(CH3)2CHCH 2 CH(NH 3)COO

2.6.1.6

+
+
(CH3)3N(CH 2)3 CH2CH(NH 3)COO

15

ORNITHINE

H 2C
OOCC

H2N(CH 2)3NH(CH2)4NH (CH2)3NH2

2.1.3.3

F0
nit

CH 3

1.3.99.10

1.14.11.1

Glutaryl-CoA

3.5.1.2
6.3.1.2

NH4+

.7.1
1.7 .6.4
1.6 .1
.6
18
6.3.4.16
1.

F1

10 c-sucb-u

6.3.2.1

PANTOTHENATE

CH3CH2

ISOLEUCINE

3-Methylcrotonyl-CoA

CH 2
CH-COO

1.

1.

4.

1.4.1.14

H+

CH3
CH3C = CHCOSCoA

OOCCH 2CH 2CH2COSCoA

(GABA)

+
H2NCH2CH2CH2CH (NH3) COO

6.4.1.4

3-Methylglutaconyl-CoA

4-Aminobutyrate

GLUTAMATE

AT I
ON

NO2-

(CH3)2CHCH 2COCOO

OOCCH 2CH2CH2NH2

+
OOCCH 2CH 2CH (NH3) COO

H+ H+
H+ H+

D PROTONS

E NDE

AT

H+

+
H+

1.1.1.169

HOCH2 C(CH3)2CH(OH)CO NHCH 2CH2COO

+
CHCH(NH 3)COO

COOH
(CH3)2CHCHCH(OH)COO

CITRULLINE

ATP

P +1 P i

4.2.1.24

N
H

H2 N

CH3CH(OH)CHCOSCoA

Oxopantoate

Pantoate
-Alanine
3.5.1.22

1.2.1.25

CH3

CH3
CH3CH=CHCOSCoA

HOCH 2 C(CH 3)2COCOO

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

CH3CHCO-SCoA

2.6.1.32

(SAM)

3)COO

CH 3

CH3CH2

2.5.1.6

S-Adenosyl
methionine

Glutathione

2-3-Dihydroxy 4.2.1.9 2-Oxo- 1.4.1.8 VALINE

isovalerate
isovalerate

CHCOCOO

1.2.1.32

CH3

2.6.1.32

CH3

2SO 4

+
CH 3 SCH CH CH(NH )COO
3
+ 2 2

2.1.1.10
2.1.1.20

4.1.2.12
CH3
+
CHCH(NH

CH3

4.3.1.3

CH2SH
+
OOCCH(NH 3)CH2CH2CONHCHCONHCH 2COO

Bile Acids

CH2 = CCOSCoA

4.2.1.19

Glycine

.3

CHCOCOO

CHCOO

Adenosyl

6.3.2

CH3

CH

METHIONINE

Adenosyl

CH3

CH2COCH2OP

NH

+
CH 3 SCH CH CH(NH )COO
2
2
3

2.1.1.13
2.1.1.14

-Glutamylcysteine

C
H

Imidazole
acetol-P

2.7.7.4

(APS)

HCHO

C (OH)CH(OH)COO
CH3

CH 3

Carnitine

Carbamoyl-P

H3 C

CH

CH

N
Fe

ATP

NH
CH

Adenylylsulphate

CH2SH
+
OOCCH(NH 3)CH2CH2CONHCHCOO

CH

Urocanate

S-Adenosyl
homocysteine

Taurine

CH3

2.6.1.19

2-OXO ACID

1.6.6.1
1.7.99.4

F1

TRA N S L O

CH3

HO

COO-

CH2

N
HC

Desmosterol

CHLOROPHYLL

CH2
H
C

2H

1.9.3.1

HO

+
SCH 2CH2CH(NH 3)COO

2.3.1.46

CH3CH2

+
OHCCH 2CH (NH3)COO

4.1.1.70

2.6.1.-

IN

NO3-

or ting ATP
nsp 3.6.1.34 synt
h
tra
oscp

AD

HEMOGLOBIN

H3 C

HO

CHOLESTEROL

Pregnenolone

CH

.2

HO3SCH 2CH2NH2

HC

CH

3-Hydroxy- 4.2.1.17 Methyl 1.3.99.3 Isobutyryl-CoA

Isobutyryl-CoA
acrylyl-CoA

Glutamyl-P

F6

2eH
HO

2-AMINO ACID

2H+ CuB Heme a3

Progesterone

.1.1

1.3.99.7

2H+

Heme a

STEROIDS

1.2

R-CO-COO

+-

6.3.2

1.8.1.3

OOCCH 2CH2CHO
Aspartyl 4.2.1.52 2, 3-Dihydro-1.3.1.26 PiperideineSemialdehyde
dipicolinate 2, 6-dicarboxylate
Succinic
semialdehyde
OH

1.4.1.2

2.5.1.21

(Vitamin E)

Aspartyl-P

UQ

1.10.2.2

Farnesyl-PP

CH 3

-Tocopherol

Phylloquinone

_
UQ.

CuA CuA

CH3

2H+

e
as

2.3.1.76
3.1.1.21

Cyt.c

OPP
CH2

CH2OH

Menaquinone

CHO

1.1.1.105

1e-

Glutamate

3.3.1.1

H
C

OH OH HN

2.6.1.9

4.2.1.49

Homocysteine

H
P OCH 2 C

C
H

CHCH 2CH2COO

+
HSCH 2CH2CH(NH 3)COO

4.4.1.8

3-Isopropyl- 1.1.1.85 Oxoleucine

4.2.1.33
malate

4.2.1.18

+
R-CH(NH3) COO

1eCyt.bH

Cyt.c1
2UQ

(C10)

Geranyl-geranyl-PP

CHO

1.2.1.36

CH3C= CHCH 2 CH2C= CHCH 2OPP

CH2OPP

5-Aminolevulinate

RPPP

CYTIDINEtriphosphate

Imidazole
glycerol-P

CH2CH(NH 3)CH2OP

NH
CH

2.7.1.25

4.2.1.22

Cystathionine

HOCH 2CHCOS-CoA-

+
(CH3)3NCH2CH(OH)CH 2COO

Retinoate

CH3O

2.5.1.1
CH3

CH 3

2.5.1.29

6.3.4.2

CH 2.7.4.6
CH

P
Y
R
I
M
I
D
I
N
E
S

(CTP)

NH
CH

Imidazolone
propionate

Phosphoadenylylsulphate

CH3

3.1.2.4

COOH

Asparagine

NS

CH3O

Opsin

(C5)

2.5.1.32

Rhodopsin

2e- 2UQ_
.
III
2eFe-S
Cyt.bL

C(OH)CH(OH)COO

2-Isopropylmalate

+
H2NOCCH 2CH (NH3 COO

TRA

hv

1.13.11.21
COO-

Retinol esters

CH3C = CHCH 2OPP

4H+

Dimethylallyl-PP

(C40)

To Brain - VISION

(C5)

1.1.1.86

+
P OOCCH 2CH(NH3)COO

5.4.99.2

Glycine

UQH2

1.10.2.2

3.1.3.15

3.5.2.7

+
CH2CH(NH 3)COO
+
SCH 2CH2CH(NH 3)COO

1.1.1.3

(CH3)2CHC(OH)CH 2COO

1.1.1.3

5.1.99.1

2.3.1.37

2UQH2

6.4.1.3

4.2.1.18

1.2.1.16

SUCCINATE

2H+

CDP

NH 2

N
RPPP

Histidinol-P

2-Methylaceto-1.1.1.35 2-Methyl-3-4.2.1.17Tiglyl-CoA
2 Methylbutyryl1.3.99.3
acetyl-CoA
hydroxyCoA
butyryl-CoA

.4

6.3.5.4

SUCCINYL-CoA

d-CDP

N
OC

CH
CH

CONH 2
N
NH C
CH
C
HC
N
N
RP

CH2

HC

CH 2CH(NH 3)CH2OH

OC

CH3

2.7.2

4.3.1.1
-OOCCH2CH2CO.SCoA

CH2

Isopentenyl-PP

ASPARTATE

6.2.1.4

II

NH
CH

+
HOCH 2CH2CH(NH 3)COO

COO

CH3

1.2.4.2
2.3.1.61

UQH2

CH3C-CH2CH2OPP

CH3

Phytoene

Lycopene (C40)

UQ

4.1.1.33

31

1.1.1.

Methylmalonyl-CoA

4.1.1.71

2-OXO-

CO

OH OH

CHCH 2CH2COO

O-Phospho- 2.7.1.39Homoserine
homoserine

CH3
HOCH 2CHCOO

CH 3CH2COSCoA

-OOCCH2CH2COO-

FAD

4.2.1.9
2-Aceto-22-Oxo-3-methyl
2:3-Di-OHhydroxy- 1.1.1.86 3-methylvalerate
valerate
butyrate

2.1.3.1
4.1.1.41
5.1.99.1

GLUTARATE

1.3.5.1

Fe-S
Cyt.b

+
OOCCH2CH2COOCH2CH2CH(NH 3)COO

CH3COCHCOSCoA

1.1.1.41

OOCCH=CHCOO-

HC

NH
CH

Hypotaurine

3-Hydroxyisobutyrate

OOC-CH-COSCoA

FADH2

Histidinol

1.1.1.23

.1.2

CH3

FUMARATE

UQH2

NHCOR

Cerebroside

3.2.1.46 2.4.1.47
1.3.99.7

+
CH2CH(NH 3)CHO

4.1

Oxobutyrate
.3.1

H
P OCH 2 C

DP

1.17.4.1

Propanoyl-CoA

-OOCCOCH CH COO2
2

or
2H+ -

O
C

2.7.4.14

Cytosine

HN
OC

2.4.2.9

RP

Cysteate

2-Acetolactate

16

CH(OH)COOCHCOOCH2COOC

4.1.3.1

MALATE
4H+
2H+ 4.2.1.2

d-CMP

NH 2
C
CH
CH
OC
NH

P-Ribulosylformimino
P-Ribosylformimino
5-aminoimidazole- 5.3.1.16 5-aminoimidazolecarboxamide-R P+
carboxamide-R P
+

+
HO3SCH 2CH(NH 3)COO

CH3COC(OH)CH 3

NH2
N
OC
C
NH
CH
C
HC
N
N

OH OH
O

1.8.99.2

4.2.99.9

+
POCH 2CH2CH(NH 3)COO

4.2.99.2

2.3.1.

4.2.1.3

CH3CH(OH)CH2CO.SCoA

1.6. 5.3

Diphosphomevalonate

CH3(CH2)12CH=CHCH(OH)CHCH 2O- Galactose

Succinylhomoserine

4.1.3.7
CH2COOC(OH)COOCH2COO-

ISOCITRATE

2H

2Fe -S
(5 Clusters)

4H+

Psychosine

CH3(CH2)12CH=CHCH(OH)CHCH 2OH

HO2SCH 2CH2NH2

CITRATE

C-COO
RP

NH
CH

4.4.1.1

CYSTEINE

COO

Methylmalonyl
semialdehyde

Glyoxylate
Cycle

1.1.1.37

CH2COO

Acyl-CoA

Histidinal

HSO -

1.8.99.1

Cysteine
sulphinate

CH3CH2COCOO

CH3
OHCCHCOO

-OOCCHO

FMNH2

CH3C(OH)CH 2CH2OPP
+
NH 3
CH3(CH2)12CH=CHCH(OH)CHCH 2O- Galactose

UDP-Galactose

NHCOR

CHOLINE

2.7.1.32

4.1.3.2

2.7.1.36
2.7.4.2

+
HOCH 2CH2N(CH 3)3

+
OCH 2CH2 N(CH 3)3

Choline-P

2.4.1.23
3.5.1.23

2.4.1.62

-CAROTENE (C40)
Metarhodopsin

2.3.1.6

4-Sphingenin

1.1.1.102

2.7.8.3

2.7.7.15

3.1.4.12

CH COO

2
Acetylcholine CH C(OH)CH
3
2 CH2OH
3.1
.4.2
Mevalonate

3.1.4.3

CDP-choline

1.1.1.32

CH3COCH 2CH2N(CH3 )3

3.1.4.4

+
CPP-O CH2CH2N(CH 3)3

Sphinganin

SPHINGOMYELIN

Mevaldate

Ethanolamine

Glycerophosphocholine

CH
OC N CH
RP

CH
N RP

NH2
C
CH
CH

3.5.4.1
O
C

HN

C
C

OC

d-UMP

.4

CH

O
C

HN
H2 N C

(GMP)

CH
CH
N DP
3.5.4.12

(PAPS)

4.2.1.16

4.1

4.1.3.8

CH2COO
CH3C(OH)CH 2CHO

+
HOCH 2CH 2NH 3

+
CH2OPO CH2CH 2N(CH 3)
O

3.1.1.5

2.7.8.2

+
NH 3
CH3(CH2)14CH(OH)CHCH 2OH

XXX

52

2.6.1.1

NAD+

18

FMN

HS

CH3COC(OH)CH 2CH3

4.2.1.

1.1.1.34

Oxalate

Glycol
aldehyde

CH2OH

- Lysolecithin

HOOC-COOH

HOCH 2CHO

HOCH O

+
CH2OPO CH2CH2N(CH 3)3
2.1.1.17
O
CH2OCH=CHR
2.1.1.71
CH 2 O-CO-R
R-CO-OCH O
3.1.1.32
O
R'-CO-OCH
+
+
CH2OPO CH2CH2N(CH 3)3
CH2OPOCH2CH2N(CH 3)3
O
O

-OH--Methylglutaryl-CoA

1.4.3.8

2.7.1.82

Ethanolamine-P

CH2O-CO-R

2.7.8.5

OPhosphatidylglycerol

HOCH O

Choline
plasmalogen 1.3.1.35
Serine +NH

Glycolate
1.2.1.21

CH2O-PO CH 2CHOHCH 2OH

+
CPP- OCH 2CH2 NH3

2.7.8.1

HOCH 2COO

HC

1.1.1.23

+
.8 HSCH 2CH(NH
3)COO

18

4.1.1.32

OXALOACETATE

OC

O
C

2.4.2

N H

CH
N RP

P
U
R
I
N
E
S

GUANOSINE-P

HN
OC

THYMIDINE-P

1.13.11.20

4.1.3.

Malonic
semialdehyde

1.

1.2.1.18

-OOCCOCH COO2

NADH+H+

CH3C(OH)CH 2COSCoA

O
C

6.3.4.1
6.3.5.2

2.4.2.

.1

C-CH3
CH
2.1.1.45
OC
N
DP

CH
CH

C
C

XANTHOSINE-P

2.7.4.8

.4.9 HN

(XMP)

2.7

O
C

HN

1.1.1.205 OC

1.17.4

CH
N RP

(IMP)

3.5.4.

GDP

RP

C
C

6.3.4.4

Guanine

C
A
T
E
C
H
O
L
A
M
I
N
E
S

CH
N

INOSINE-P

3.1.4.6

2.7.4.6

Formimino
glutamate

1.6.4.1

1.1.1.39

4.1.3.4

CH2COO

1.2.3.5

1.6.5.3

Cardiolipin

O
+
CH 2O P OCH 2CH2 NH 3

2.3.1.50

R'-CO-OCH

CH2 O-POCH 2CH(OH)CH 2 O-P-OCH 2

O
O

R'-CO-OCH

CDP-diacyl
glycerol

CH2O-CO-R

O HCO-CO-R

Glyoxylate
1.1.1.79

Inositol

2.7.8.11

4.1.3.5

OHCCOO

2.7.7.41

CH2O POCMP

Serine

CH 2O-CO-R

CH2O-CO-R
R'-CO-OCH
O

4.1.1.65

CH 2O-CO-R

CH 2O-CO-R

R'-CO-OCH

1.3.99.7
HO OH

Aspartate

.1

O
C

HC

2.4.2.1

1.1

O
C C
NH

3.5.4.10

Adenylosuccinate

Uracil

HN

HN

+
CH3CH(OH)CH(NH 3)COO

OHCCH 2COO-

ACETYL-CoA

NAD+

1.3.1.2

CH
C-COO
NH

3.5.4.19

4.1.1.29

GTP

CH3COSCoA

H2 N
HCO

HN

7.4

O
C

HN
OC

O
C

P OCH 2

.99

THREONINE

LACTATE

CH 2O-CO-R
OH

CH2O-PO

+
CH3(CH2)12CH=CHCH(OH)CHCH 2O PO CH2CH2N(CH 3)3
O

Austria
SIGMA-ALDRICH HANDELS GmbH
Tel: (+43) 1 605 81 10
Fax: (+43) 1 605 81 20

6.4.1.1

2.4.2.1

d-GDP

2.4.2.4

Thymine

OOC

HO2SCH 2COCOO

2.6.1.18

2.

2.4.2.15

TDP

O
C

HN
OC

NH
CH

4.1.2.5

4.

NH

.6

Dihydrouracil

CH-COO
NH

+
HO 2SCH 2CH(NH 3)COO

CH3CH(OH)COO

HOH
GDP
CO2

1.2.4.1
2.3.1.12
3.1.3.43

NADH+H+
4.1.3.5

3-Oxopentanoyl-CoA

3.5.2.2

RP

3.1.3.

Inosine

3.2.2.

CH

A
C
I
D
S

Formylamidoimidazolecarboxamide-R P

4.3.1.3

4.2

CYSTINE

4.1.1.12

.1.2

CH2O-CO-R
R'-CO-OCH O

NHAcyl

Australia
SIGMA-ALDRICH PTY LTD.
Free Tel: 1800 800 097
Free Fax: 1800 800 096
Tel: (+61) 2 9841 0555
Fax: (+61) 2 9841 0500

1.1

C
C

4.3.2.2

.7.6

CH2
CH2
OC
NH

CH2

HISTIDINE

CH2CH2NH2

3-Sulphinyl
pyruvate

ALANINE

18

HC

2.7

C CH3
CH
NH

1.3.1.2

CH

2.1.2.3

d-CTP
GTP
TTP 2.7.4

O
C

HISTAMINE

+
S-CH 2CH(NH 3)COO
+
S-CH 2CH(NH 3)COO

.1.44
2.6.1.4 2.6

Gangliosides

Argentina
SIGMA-ALDRICH DE ARGENTINA S.A.
Free Tel: 0810 888 7446
Tel: (+54) 11 4556 1472
Fax: (+54) 11 4552 1698

16

2.3.1.9

CH3COCH 2COSCoA

Acetoacetyl-CoA
CH3CH2COCH 2COSCoA

1.1.1.35

3-OH-Pentanoyl-CoA

2.3.1.

3-Oxohexanoyl-CoA

1.1.1.157

3-OH-Butanoyl-CoA

16

CH3(CH2)2COCH 2COSCoA

1.1.1.35

CH3(CH2)2CH(OH)CH 2COSCoA

Dihydro
thymine

+
CH2CH(NH 3)COO

HC

+
CH2CO-OCH2CH(NH 3)COO

+
CH3CH(NH3)COO

4.1.3.

CH3COCOO-

NAD
ATP
CO2

2.3.1.

3-Oxoacyl-CoA

HSO32.6.1.2

HN

d-GTP

.7.7

HN
OC

P-Ribosyl-AMP

4.4.1.15

1.4.1.1

1.2.4.1
2.3.1.12
1.8.1.4

2.3.1.38

CH3(CH2)n COCH 2COSCoA

1.1.1.35

3-OH-Acyl-CoA

NHCOCH 2CH2NH2

Acetylserine

4.4.1.15

PYRUVATE

O
C

Fumarate

2.7

CH-CH3
CH 2
NH

C N

H 2N

NH
N
C
C
N
CH
C
HC
NH RP
N

2.7.7.7

2.7.7.6

O
C

H 2N

RP

Plant Pigments

OOC-CH-CH 2COO

2.7.7.7

NH

.1.1

4.1.1.9

CH 3CO-S-ACP

Acetyl-ACP

3.1.2.11

Odd C Fatty acids

CH 3(CH2)14COCHCH 2OH

P
O
R
P
H
Y
R
I
N
S

1.1.1.30

Acetoacetate

Phosphatidate

3.6.1.31

Carnosine

C
C
H

4.1

ATP

.1.2

Malonyl-Co-A

CH3COCH 2COO

CH3(CH n CH(OH)CH 2COSCoA

.1.3

Acetaldehyde

PYRUVATE
CH3(CH2)n CH=CHCOSCoA

2.3

2.1.3.2

CH3CHO

3.7

HOOCCH 2CO-SCoA

CH3(CH2)n CH2CH2COSCoA

Dehydrosphinganin

S
T
E
R
O
I
D
S

4.1.1.4

3.1.1.28

OH

I
S
O
P
R
E
N
O
I
D
S

CH3CH(OH)CH 2COO

Acetone 3-OH-Butyrate
2.7.8.5

NH
C
H

2.7.1.40

2.3.1.39

CH2O P

Diacyl

FAT

HOOCCH 2CO-S-ACP

Malonyl-ACP

CH

Adenine

NH2
N
+ C
C
N
CH
C
HC
N
N
RP(PP)

C CH 2CHCOO

ETHANOL

ADP

KETONE BODIES

CH3COCH 3

R-CO-OCH

CH2OH

HC

1.2.1.4

HS

CH2O P

3-P-Glycerol

CH2O-CO-R

CH2O-CO-R
R-CO-OCH

R-CO-OCH

O-Acyl-carnitine

Phosphatidyl
inositol

P
H
O
S
P
H
O
L
I
P
I
D
S

CH2O-CO-R

3.1.1.3

2.7.1.30

Acetoacetyl-ACP
2.3.1.41

2.3.1.51

4.1.1.22

1.1.1.1

CH3COCH 2COSACP

1.1.1.8

HOCH

Glycerol

(Cytosol)

2.3.1.7

CH2OH

CH2OH

HOCH
CH2OH

OH OH
O

2.3.1.41

3-OH-Butanoyl-ACP

H
C

P-enolpyruvate

Tannins

URIDINEDihydro
Orotate
Orotidine-P
Uridine-P
UDP
4.1.1.23 (UMP) 2.7.4.4
2.4.2.10
2.7.4.6 triphosphate
orotate 1.3.1.14

3.5.2.3

P-Ribosyl-ATP

Glycerate

CH2=C(OP ) COO

CH3(CH2)2COCH 2COSACP

1.1.1.100

P OCH2 C

2.4.2.17

CH 3(CH2)6COCH 2COSACP

3-Oxo-Hexanoyl-ACP

CH3CH(OH)CH 2COS-ACP

R-CH2COO

P-Hydroxypyruvate

4.2.1.11

H 2N

ADENOSINE-P

O
C

O
C

LIGNIN

5-Amino-4-imidazole 4.3.2.2 5-Aminoimidazole

(N-succinylcarboxamide)-R P
carboxamide-R P

(AMP)

Carbamoyl
-alanine
HN
OC

OH

THYROXINE

6.3.2.6

O
C

CH3CH 2OH

2.3.1.41

3-OH-Hexanoyl-ACP

4.2.1.58

3.5.1.6

Coumarate

OOC-CH-CH 2COO
HNCO C N

RP

.7.6

3.5.2.2

CH=CHCOO

(UTP)
2.6.1.22

2.6.1.52

3-Oxo-Decanoyl-ACP

1.1.1.100

2.7.4.3
2.7.4.4

Cinnamate
Menaquinone

1.14.13.11

OH

1.1.1.204
1.1.3.22
Hypoxanthine
1.1.3.22 Xanthine

RNA

P OCH2COCOO

3-Oxoacyl-ACP

NH

NH2 N
C
C
CH
C
HC
N RP(P)
N

H2NCONHCH 2CH 2COO

Carbamoyl
aspartate

HOCH2CH(O P)COO

2.3.1.41

CH3(CH2)2CH(OH)CH 2COSACP

4.2.1.59

13

A
M
I
N
O

1.3.1.13

CH=CHCOO

OH

Tyramine

ADP

HN
OC

4.2.1.51

A
R
O
M
A
T
I
C

Phenylpyruvate

CH
N

HN

HN

1.

-OOC
NH2 CH2
OC
CH-COO
N

1.1.1.29

2-P-Glycerate

2.7.7.6

-Ureido
isobutyrate

1.

ACETATE

Mitochondrial

3-OH-Decanoyl-ACP

CH3CH=CHCO.S-ACP

CH3CH2CH2COSACP

ACYL-CoA

D
E
G
R
A
D
A
T
I
O
N

3-OH-Acyl-ACP

2.

-Alanine

HOCH2CH(OH) COO

5.4.2.1

3.5.1.6

CH 3COO

CH 3(CH2)n COCH 2COSACP

1.1.1.100

60 CH3(CH2)6CH(OH)CH 2COSACP 1.1.1.100

CH3(CH2)6CH=CHCOSACP

2, 3-Decenoyl-ACP

1.3.1.9

POCH2CH(OP) COO

2, 3-Diphosphoglycerate

NH

MELANIN

2.7

H2NCONHCH 2CHCOO

H2NCH 2CH2COO

HC

Endoplasmic Reticulum
Chain elongation

3, 4-Decenoyl-ACP

1.3.1.

Thromboxane B2
CH3(CH2)14COCH 2COS-CoA

CH 3(CH2)n CH(OH)CH 2COSACP

4.2.1.60
4.2.1.61

CH3(CH2)5CH=CHCH 2COSACP

Decanoyl-ACP

OH

4.1.1.11

Phosphoserine

2.7.1.31

Oxostearoyl-CoA

CH3(CH2)14COCH 2COS-CoA

CH 3(CH2)14COSCoA

CH3(CH2)6CH2CH 2COSACP

5.3.99.5

Prostaglandin PGE 2

Palmitoyl-CoA

ACYL-ACP

OH

HO

O
O

N
C
CH
C
OC
NH
NH

CO

DNA

.7

CH3

3-Aminoisobutyrate

4.2.1.22

+
P OCH2CH(NH3)COO

1.1.1.95

3-P-Glycerate

COO

OH-Stearoyl-CoA

CH3(CH2)n CH=CHCOS-CoA

1.3.1.9
2,
1.3.1.10

COO

COS-CoA
CH3(CH2)14CH(OH)CH 2COS

CH3(CH2)14CH=CHCOS-CoA

Dehydrostearoyl-CoA

Palmitoyl-ACP

HO

Palmitoleoyl-ACP
COSCoA

Stearoyl-CoA

B
I
O
S
Y
N
T
H
E
S
I
S

5.
1.1 3.99
4.9 .3
9.1

CO-S-ACP

POCH2CHOH COO

OH

N
H

CH2CH2NH2

.1.2

1.17.4.1

20

3.1.3.3

Hydroxypyruvate

ATP

COO

Leukotriene B4

SERINE

HOCH2COCOO

ADP

C
C

URATE

2.7.4.6

ATP

4.2.1.

CH3
H2NCH 2 CHCOO

HOCH2CH(NH3)COO

P-Ribosyl-PP

HO

COO

4.6.1.1

ATP

4.1.2.5

CHOLINE

1:3-bis-P-Glycerate

OP O P

FOLIC
ACID
C1
POOL

+
HOCH2CH2N (CH3) 3

2.7.2.3

Arachidonate 1.13.11.34

Allantoin

2.7.7

Betaine
aldehyde

OH OH

1.7.3.3

NH

d-ATP
2.1.2.1

2.6.1.51
1.4.1.7

OC

2.7.4.6

OHCCH 2N(CH3)3

1.2.1.12

HN

d-ADP

1.1.99.1

1.2.1.13

3.6.1.34

-Linolenate

OH

Cyclic AMP

2.4.2.14

OH OH

1.4.4.2

1.2.1.8

6.3.4.7
Pi
NAD+

H2 N

RP

NH2
N
N
CH
O
O HC
O
N
N
-O P~O P~O P O CH
2 O
O
O
O

CH

N
CH2 O

2NHCH3

Betaine

Pi

CH2OP
O

ATP

C
N H NH
H

2.1.1.5

.1
5.3.1
2.7.1.28

2.7.6.1

NH2

Dimethylglycine

NADH

Fixation

ATP

3.5.2.5

Glyceraldehyde

CO2

ATP

.1

5.3.1

(Glycerone-P)

Ribulose-1,5-bis-P

NH

HC

1.5.99.2

3-P-Glyceraldehyde

4.1

C
C

CH
N

NH
CO

OC

OC

OOCCH2N(CH3)3

HOCH2COCH2OP
2.2.1.1

ADP

Pi

OOCCH 2N(CH3)2

4.1.2.13

COO

1.3.1.35

Glyoxylate

Sarcosine

POCH 2CHOHCHO

NADP+

ATP synthase
e

1.14.99.25

2.
OOCCH

Sedoheptulose-PP

CHLOROPLAST OUTER MEMBRANE

Linoleate

NH2

C
N H
H

H2 N

Allantoate

.1.4
2.6 .10
.1
20
1.4
1.
1.

GLYCINE

CH2OP
O

RP

OOC

HC
H 2N C

CHO
NH

CH2COCOO

PHENYLALANINE

Ubiquinone

Prephenate

2.6.1.5
4.3.1.
5

1.3.1.13

HN

CH 2COCOO

1.14.18.1

Plastoquinone

NH2
CO

COO

OC

CH2(NH3)COOH

CO CH2OP

Fructose1:6-bis-P

2.2.1.2

H 2N

3.5.3.4

2.2.1.1

H+

STROMA

Dopaquinone

NH

H 2C

HN C

RP

Urea

OH OH OH H

D-Ribose-5-P

H+

THYLAKOID MEMBRANE

OCH 3

1.14.16.1

2-Amino
muconate

OH

5.4.99.5

Chorismate

CH2CH(NH3) COO

H2
C
CH-COO
+
NH3

(Vitamin E)

OOC

4.1.3.27

NH 2

OOC
OOC

Anthranilate

CH2CH(NH3) COO

Dopa

1.14.18.1

-Tocopherol

1.14.12.1

NH2

2.4.2.18

OC-COO

OH

4.6.1.4

TYROSINE

1.2.1.32

COO

CH2

O-C-COO

Shikimate-5
enolpyruvate 3-P

6.3.3.1
5-Amino 4.1.1.21 5-Amino-4-imidazole
Formyl 6.3.5.3
Formyl
carboxylate-R P
imidazole-R P
glycinamide-R P glycinamidine-R P

6.3.4.13

ADP

NH

OH

4.1.1.28

Dopamine

CHOHCH 2OH

CHO

OC

H2NCONH 2

OH OH H
CO CH 2OH

D-Xylulose-5-P

flo

ADP

H+

ATP

1.14.17.1

.1.6

NH

H 2C

2.1.2.2

2.7.1.11

3.1.3.11

Erythrose-4-P

NHCOCH 2NH2

OH OH

Glycinamideribosyl-P

CH CH2OP

CH2CH(NH3) COO

1.14.16.2

OH

OH

4-OH-3-Methoxyphenylglycol

CO CH2OH

OH OH

OH OH OH

H+

THYLAKOID LUMEN

C CHO

POCH 2 C

OH H

H+

HO

POCH 2

H+

OH

OH

N-(5-P-Ribosyl)
anthranilate

+
CH2CH(NH3) COO-

CH2CH2NH2

OH

OCH
NH2
COO

COO

OH

OH

2.6.1.5

Hydroxyphenyl
pyruvate
1.3.1.13

2.1

1.4

OH OH

4.1.1.48

P O

2.5.1.19

Shikimate-3-P
PEP

OH

1.13.11.27

Homogentisate

(Normetadrenaline)

NH

COO

OH

OH

(Noradrenaline)

CHOHCH 2NH2

4-OH-3-MethoxyD-mandelate

OH OH H

OH OH

H+
H+

H+

PC PC

H+ H+
H+
H+ H+
H+ H+ H+ H+
H+
H+ H+
Protons from Water
H+
H+ H+
H+ H+ H+ H+ H+ H+
H+

H
POCH2 C

Fructose-6-P

OH OH

5.3.1.6

OH

.3.4

P O

CH2COCOO

OH

Normetepinephrine

OCH 3

CH2OP
O

CO CH2OH

5.1.3.1

Fe-S 2e- Cyt.f

H+

O2

NADPH+H+

H+

H+
H+

Translocated protons

H+

2.2.1.1

OH OH OH

H+

A1

4H+

H 2O

OH

HO OH

Shikimate

Quinolinate

COO

2.7.1.71

COO

N-Acetyl-5-O-methyl-serotonin

OCH
NH2
COO

1-(o-Carboxy phenylamino)
1-deoxyribulose-5-P

OH

OH

COO

NH

2.1.1.4

NH2

OH

COO

CH2COO

Norepinephrine

OCH 3
OH

CH(OH)COO

OH

NADPH

5.1.3.1

(Adrenaline)

CH2 OP
O

OH

2.1.1.28

Epinephrine

5.3.1.9

5.3.1.8

1.1.1.44

H+

Chl.A0
2PQ

NADP +

NADP +

CH2OP

CHO

3
3

2e-

ren
t)

2
2

2PQ

2e-

C COO -

.1.1

H+

Fe-S

2e-

Mn

.17

OH
OH

2.7.1.2
2.7.1.1

1.1.1.25

CHOHCH 2NH2

CHOHCH 2NHCH 3

ATP

Glucose-6-P

P-Glucono
lactone

.1
3.1

Maleyl
acetoacetate

ADP

1.1.1.49

1.13.11.5

2.4.2.19

CH2
HO

OH

Dehydroshikimate

OH

2.4.2.19

4.1.1.45
3-Hydroxy 1.13.11.6 2-Amino-3-carboxy
2-Aminomuconateanthranilate
muconate semialdehyde
6-semialdehyde
COO
H H
Catechol

3.7.1.3

COO
HOC-CH(OH)CH(OH)CH 2OP
CH
N

COO

OH

4.2.1.10

O
CH2COO

COO

5.2.1.2

COO

OH

OH

Quinolinatenucleotide

CH 2CH2NHCOCH 3

CH3O

COO

NH2

3-Hydroxy
kynurenine

C-CH(OH)CH(OH)CH 2OP
CH

Indole-3-glycerol-P

COO

Dehydroquinate

O
CH2COO

Fumaryl
acetoacetate

GLUCOSE

2.6.1.16

OH

D-Ribulose-5-P

2.7

1e-

Cyt bf

2PQH2

2.7.1.17

*2e

Cyt bc
_ 2e-

P680
Chl.a

POCH2

CH2OH

CO

Ferredoxin

2e-

PQ

PQH2

QA

Pheophytin

OH H

OH

4.6.1.3

3-Deoxy-D-arabinoheptulosonate-7-P
-OOC

3.1.3.9

HO OH

.1.4

CH2OH

5.1.3.4

QB

CO

D-Ribose

OH

2.7

H+

2H+

PQH2

Ribitol

D-Xylulose

PQ

CHO

PHOTO- H+
otophosphoryla SYSTEM
lic
n-cyc electr
tion l
2H+ yclic Ph
No (electric cur on
C

2e-

OH

H+

H+

PHOTOSYSTEM
II

OH OH OH

OH H

H+

OH OH H

C CH2OH

OH

4.2.1.20

TRYPTOPHAN
HO

5.4.2.2

NH

4.1.1.28

HOCH HCOH
C

Kynurenine

+
CH2CH(NH 3)COO

COO
OC
P OCH 2 CH2

CH2OH
O

HO OH

1.1.1.

OH OH H OH
6-P-Gluconate NADPH

OH

OH

HOCH 2 C

Fructose-1-P

CH2OH

POCH2 C

.9

NH

Tryptamine

OPPU

OH

HO

3.2.1.48

CH2OP
O

2.7.1.3

HOCH 2 C

2.7.1.47

OH OH

1.1.1

OH OH H

CH 2OH
O

+
COCH2CH(NH 3)COO
OH

1.14.13.9

+ COO
N RP

(MELATONIN)

+
CO CH2CH(NH 3)COO

1.13.11.11

CH2CH 2NH2

OH

Glucose-1-P

OH

21

Sorbitol

CO

D-Xylose

CO CH2OH

HOCH 2 C

1.10.2.1
1.10.3.3

CO
O

L-Ribulose 2.7.1.16 L-Ribulose-5-P

L-Lyxose

OH H

POCH2

HOCH 2 C C
OH H

OH OH

CHO

OH OH

CO

CO CH 2OH

L-Xylulose-5-P

CH 2OH

Xylitol

.1.4

POCH2

2.7.1.53

OH H

5.3

HOCH 2

2.4.1.22

OH

3.2.1.26

SUCROSE

OP
OH

NH

11

Nicotinatenucleotide

CH2CH2NHCOCH 3

NH

NH2

3.5.1.9

Formylkynurenine

Indolepyruvate

HO

COO

COO

NICOTINATE

2.4.2.

Ribose- P

2.7.7.18

Desamino-NAD

CH 2CH2NH 2

+
N

(SEROTONIN)

+
CO CH2CH(NH 3)COO
CHO

NH

4.1.99.1

NH

UDP-Galactose

OP
P

Glucosamine-6-P

OH OH H

HO
5.1.3.2
2.7.7.10

NH2

5.3.1.8

CH2OH

CO

Dehydroascorbate

HOCH 2 C

CH 2OH

L-Xylulose

OH OH H
C

CO

OH
C

OH OH

OH

H
C

1.1.1.14

OH H

H
C

CH 2COCOO

OH

2.7.7.12

CH 2OH
O
HO OH

HO OH

2.3.1.

5.5.1.4

CO

OH H

OH H

CHO

OH H

D-Arabinose 5.3.1.3 D-Ribulose

4.1.1.34

OH OH

HOCH 2 C

OH
C

OH OH H

L-Arabitol
HOCH 2

H
C

HOCH2

2, 3-Dioxogulonate

ASCORBATE

CO COO -

CO

OH

HOCH 2

1.1.1.130

3-Dehydrogulonate
HOCH 2 C

HOCH 2 C

OH OH

2.4.1.9

Fructose

Inositol-P

OH H
H

OH H

C COO-

CO

HOCH 2

2.7.7.9

CH 2OP
O

NHCOCH 3

OH

OH

3.1.3.25

Inositol

CO

Gulonolactone 1.1.3.8 2-Oxogulonolactone

1.1.1.45

OH

2.7.7.27

2.4.1.13

N-Ac-Glucosamine-6-P

HO OH
OH

1.13.99.1

OH H

HO OH

OP

HO OH

OH

Glucuronate

CO

OH
OH

OH

1.1.1.19
OH OH

OH

HO OH

OH H

OP
NHCOCH 3 5.4.2.3

N-Ac-Glucosamine-1-P

HO

2.7.7.24

Mannose-6-P

OPPU

UDP-Glucose
Galactose-P

2.7.7.34

TDP-Glucose

CH 2OP
O

HO OH HO OH

CH2OP
O

2.7.7.23

GDP-Glucose

HO

1.14.16.4

5-Hydroxytryptamine 2.3.1.5 N-Acetyl-serotonin

4.1.1.28

5-Hydroxytryptophan

Indole

4.1.1.43

CH2OH
O

2.7.1.6

NH

NH

NH

Ribose - O - P - O - P - O -Adenosine

6.3.5.1
6.3.1.5
HO

COO

+
CH2CH(NH3)COO

HO

Indoleacetaldehyde

Ribose -O - P - O - P - O- Adenosine(P)

NAD( +P)

CH2CHO

GALACTOSE

HO OH

1.1.1.22

5.4.2.8

CH2OH
O

NHAC

5.1.3.14

4.2.1.46

(Auxin)

3.2.1.23
2.7.1.38

OH

OH

CH2OH
O
OH

Indoxyl

1.2.3.7

OH

OH

ADPGlucose

NH

Indoleacetate

CH2OH
O

2.4.1.1 2.4.1.11 HO
etc.
2.4.1.21

OPPT

OH

OH

MANNOSE

2.7.7.13

HO OH HO O P

UDP-Glucuronate

4.1.3.20

HO OH

N-Ac-Mannosamine

Gulonate

P
H
O
T
O
S
Y
N
T
H
E
S
I
S

CH2OH
O

2.4.1.21

OH

NH

OH

OH

LACTOSE

TDP-4-Oxo6-deoxyglucose

HO OH HO OH

5.1.3.6

OPPU
OH

5.1.3.13 O
CH2OH
O

2.7.1.60

ACNH
HO OH
OH

3.1.1.18 HOCH 2

P
E
N
T
O
S
E
S

OPPU

CH3

2.4.1.33

GDP-Mannose

OH

5.1.3.7

OH OH

HO OH HO OPPG

UDPGalacturonate

COO

CH2OH
O

4.2.1.47
O

OH

UDP-N-AcGalactosamine

OPPU
NHAC

UDP-N-AcGlucosamine
pyruvate
N-Ac-Mannosamine-6-P
CH2OH
O

COO -

NHCOCH 3

3.1.3.29
ACNH
4.1.3.20
HO OH
OH

H
E
X
O
S
E
S

5.1.3.12

OPPU

OH

OH 2.7.7.43

CH2OP
O

CH2OH
O COO

O
OH

2.4.1.29

TDP-Rhamnose

GDPMannuronate

OH

CH2OH
O

OH
OPPT

GDP-Fucose

2.4.1.16

COO

HO CH3

HO OPPG

HO

HO

O
CH3

OH

UDP-N-Ac-Muramate

1.1.1.132

2.4.1.68
2.4.1.69
OPPU

OH

UDPIduronate

COO-

HO

CMP-N-Acetyl
neuraminate
AcNH

HO

2.4.1.17

CH2COO
CH2OH
O

.5

CHOH
CHOH

AcNH

COO

CONH 2

GLYCOGEN

6.
3.
5

GLYCOPROTEINS
GANGLIOSIDES
MUCINS

19
1.
4.
1.

P
O
L
Y
S
A
C
C
H
A
R
I
D
E
S

HOCH
HC

CH2
CHCOO

3-Hydroxypyrroline5-carboxylate

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

1.5.1.2

Creatinine

Proton Flow

Small Numbers ( eg. 2.4.6.7) refer to the IUBMBEnzyme

Commission (EC) Reference Numbers of Enzymes

22nd Edition Designed by Donald E. Nicholson, D.Sc.,

The University of Leeds, England and Sigma-Aldrich Cat. No. M3782
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