sigma metabolic pathways

Page 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

TRANSAMINATION

2H+

2H+

+

CO2

5-Amino-levulinate

Glycine

H+H+

H+H+

H+H+

c

H+ H+

F0

F1

F1

!2

1 "!

"

#

0 c-sub-units

AD

P+ Pi

3.6.1.34

H

+-transporting ATP synthase

"

$F6

oscp

ATP

ADP +Pi

FUMARATE

UQH2

UQ

UQH2

NADH+H+CH2COO-

C(OH)COO-

CH2COO-

CH(OH)COO--

2COO-

-OOCCOCH2CH2COO-

-OOCCH2CH2CO.SCoA

-OOCCOCH2COO-

CH3CH(OH)CH2CO.SCoA

-OOCCH=CHCOO-

Glyoxylate Cycle

-OOCCHO

GTP

GDPATP

+

HEME Protoporphyrinogen Coproporphyrinogen Uroporphyrinogen Porphobilinogen

5-Amino-levulinate

COO-

CH2

CH2H2NCH2C=O

FADH2

FADCyt.b

Fe-S

SUCCINATEII

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

1.2.4.12.3.1.123.1.3.43

4.1.1.32

4.1.3.7

4.2.1.3

1.1.1.41

1.2.4.22.3.1.61

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

2.6.1.12.3.1.16

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

1.6.6.11.7.99.4 1.7.7.1

1.6.6.4

1.18.6.1

2.3.1.37

1.10.2.2

1.10.2.2

#

%$

!

33 !ATP

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+

GlyceraldehydeRibulose-1,5-bis-P

2!

88

H+c

32

%

a

32

"1

"

%

"

!2

1

3

"

"!

3

"

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 flow

2e-2e-

Mn2e-

*

Protons from Water

H2O

H+

H+

2H+

2H+

#CO2Fixation

H+

ADPPi

H+

NADPH+H+

ATPTHYLAKOID MEMBRANE

CHLOROPLAST OUTER MEMBRANE

THYLAKOID LUMEN

STROMA

(electric current)

P680Chl.a

QA

QB

Pheophytin

P700

Chl.A0

A1

Fe-S

ATP

ADP

ATP

1/2O2

H2O

PQH2

To Brain -

AMINO

ACIDS

PYRIMIDINES

PURINES

CATECHOLAMINES

AROMATIC

AMINO

ACIDS

hvVISION

LIPID

PHOTOSYNTHESIS

PORPHYRINS

STEROIDS

ISOPRENOIDS

PHOSPHOLIPIDS

DEGRADATION

LIPID

BIOSYNTHESIS

PENTOSES

HEXOSES

POLYSACCHARIDES

COCH CH(NH )COO2 3+

FOLICACID

C1POOL

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 GROUPSUBSTANCES

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

OPPTO

OH

OH

O

OHACNH

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

pyruvateN-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

RibitolL-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 HO

HOCH2 C C C C CO

OH OHH OH

H HO

HOCH2 C C C CO CO

OHH

H

OH H

C C

OH

CO

P-Ribosylamine

Glycerate2, 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

HOCHP

Glycerol

UDP-GalactoseUDP-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-Hydroxykynurenine

3-Hydroxyanthranilate

2-Amino-3-carboxymuconate 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

NH

C-CH(OH)CH(OH)CH O2 PCH

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 2.5.1.19Shikimate-3-P Shikimate-5enolpyruvate 3-P

ChorismatePEP

2.7.1.71

1.4.1.19

Homogentisate Phenylpyruvate

Cinnamate

Coumarate

Prephenate

2-Aminomuconate

Fumarate Aspartate

GLYCINE

Sarcosine

Hydroxy-pyruvate

P-Hydroxy-pyruvate

SERINE

Imidazoleglycerol-P

P-Ribosyl-ATP P-Ribosylformimino5-aminoimidazole-carboxamide-R P

Formiminoglutamate

Imidazolonepropionate

Urocanate

Cystathionine Homocysteine

Phosphoadenylyl-sulphate

(PAPS)

CH (NH )COOH2 3+

Histidinol-PHistidinolHistidinal3.1.3.15 2.6.1.91.1.1.23

3.6.1.31

5.3.1.162.4.2.17

Asparagine

ALANINE

3-Sulphinylpyruvate

Oxobutyrate

2-Aceto-2-hydroxy-butyrate

O-Phospho-homoserine

HO SCH CH NH2 2 2 2

HypotaurineHO SCH CH NH3 2 2 2

Taurine

Glutamate

#-Glutamylcysteine

Glutathione

Glycine

Cysteine

ß-Alanine

Cysteate S-Adenosylhomocysteine

4.2.99.2

1.1.1.864.2.1.9

1.1.1.86 4.2.1.92.6.1.32

4.1.3.18

S-Adenosylmethionine

(SAM)

2-Methylaceto-acetyl-CoA

2-Acetolactate 2-3-Dihydroxyisovalerate

2-Oxo-isovalerate

3-Hydroxy-isobutyrate

3-Hydroxy-Isobutyryl-CoA

Methylacrylyl-CoA

2-Methyl-3-hydroxy-

butyryl-CoA

Tiglyl-CoA 2 Methylbutyryl-CoA

2:3-Di-OH-3-methylvalerate

2-Oxo-3-methylvalerate

Isobutyryl-CoA

Cysteinesulphinate

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

OHOHO

COO

OHOH

HO P

COO

OHOH

O

CH2

P

COO

O-C-COOOH

OOH

OOC CH COCOO2

N H

HOC-CH(OH)CH(OH)CH 2OPCH

COO

NH2

COO

OHNH2COO

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

#-Linolenate Arachidonate Leukotriene B4

COSCoA

CO-S-ACP

Thromboxane B2

HOOCCH CO-S-ACP2Malonyl-ACP

HOOCCH CO-SCoA2

Malonyl-Co-A

CH CO-S-ACP3

Acetyl-ACP

CH O-CO-R2

CH OH2

R’-CO-OCH

FATTY ACIDACYL-CoA(Cytosol)

CH O-CO-R2

CH O2

R’-CO-OCH

P

Cardiolipin Phosphatidylglycerol

AcetylcholineGlycerophosphocholine

Lysolecithin

Cholineplasmalogen

CDP-choline Choline-P

Mevaldate

CH (CH ) CH=CHCH(OH)CHCH OH3 2 12 2

Dehydrosphinganin Sphinganin 4-Sphingenin Psychosine

Acyl-CoAAcyl-CoA

CerebrosideGalactoseCH (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

OPPCH2

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)

"-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

OHOH

CHOHCH NHCH2 3

OHOH

CHOHCH NH2 2

4-OH-3-Methoxy-phenylglycol

CHOHCH NH2 2

OHOCH3OCH3 CHOHCH OH2

OHOCH3

4-OH-3-Methoxy-D-mandelate

Cyclic AMPATP

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

OHOCH3

CH(OH)COO

H2

NH3+

CH-COOCO

O

COO

NRibose- PN+

COO

NH

CH COO2

O

OH

CH O2 P

NHCOCH NH2 2

OHFormyl

glycinamide-R P

Urea

Formylglycinamidine-R P

Allantoate Allantoin URATE

ADP

Xanthine Hypoxanthine

Inosine

Adenine

Adenylo-succinate

5-Aminoimidazole-R P

5-Amino-4-imidazolecarboxylate-R P

5-Amino-4-imidazole(N-succinylcarboxamide)-R P

5-Aminoimidazolecarboxamide-R P

Formylamido-imidazole-

carboxamide-R P

H NCONH2 2

HNH C2 CHO

NHRP

NH

C

CCO

CCO

OCNH

NH

HN

HN

H

CCO

CCH

OCNH

N

N

HN

Carbamoylß-alanine

Dihydro-uracil Uracil

d-ADP

d-ATP

GTP GDP

XANTHOSINE-P(XMP)

TTP

TDP

ß-Ureidoisobutyrate

Dihydrothymine

Thymine d-UMP d-CMP d-CDP

CDP

Carbamoylaspartate

Dihydroorotate

Orotate Orotidine-P Uridine-P(UMP)

UDP

3-Amino-isobutyrate

CHCNH2

CHOCNH

NCHCO

CHOCN H

HN

CH-CH3CO

OCNH

HNCH2

CH2CH2

CO

OCNH

HN

CO

CHOCNH

HN C CH3

Methylmalonylsemialdehyde

OHCCHCOOCH3

CH2CO

CH-COOOCNH

HN CHCO

C-COOOCNH

HN

H NCONHCH CH COO2 2 2

CC

CCH

RPHC

NH

NH OOC-CH-CH COO2

N

N

N

CHO

NH RP

NH

OC

H C2

2.7.7.433.1.3.29

1.1.1.158

5.1.3.132.7.1.383.2.1.23

3.1.3.294.1.3.20

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

1.1.1.92.7.1.15

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

5.3.99.31.14.99.1

1.13.11.34

1.3.1.101.3.1.9

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-COOHOxalate

Glycolate

HOCH CHO2Glycol

aldehyde

Ethanolamine-P

2.7.1.30

2.3.1.7

3.7.1.2

4.1.3.5

2.7.8.8

2.1.1.172.1.1.71

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

1.2.4.12.3.1.121.8.1.4

2.6.1.21.4.1.1

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

5.2.1.31.2.1.36

2.3.1.763.1.1.21

5.2.1.7

5.4.99.71.14.99.7

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

6.3.5.16.3.1.5

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 1.1.3.221.1.3.22

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

2.6.1.511.4.1.7

3.1.3.3

2.6.1.52

2.1.3.2

ACETATE

2.4.2.4

2.1.1.45

RP

CHCO

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

4.4.1.11.6.4.1

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 2Propanoyl-CoA

1.1.1.31

2.1.3.14.1.1.415.1.99.1

6.4.1.3

6.3.2.5

2.1.1.142.1.1.13

4.6.1.1

CDP-Ethanolamine

1.1.1.35 4.2.1.17

+HO SCH CH(NH )COO2 2 3

3.5.2.7NHHN

CH

OOC CHCH CH COO2 2

CMP-N-Acetylneuraminate

CDP-diacylglycerol

CHOLINE

Ethanolamine

Glyoxylate

HISTAMINE

2.3.1.46Homoserine

Tyramine

Plant PigmentsTannins

Maleylacetoacetate

Fumarylacetoacetate

5.2.1.2

CH COO2

OH

OH

OH

CH CH NH2 2 2

OHOH

CH CH NH2 2 2

Hydroxyphenylpyruvate

"-Tocopherol(Vitamin E)

LIGNIN

d-GTP

OH

OH OH

O

HO

OH

P

OPPT

CH3HO

OHOH

O

NADPH

2.2.1.1

2.7.1.3

1.1.1.45

1.1.1.130

1.10.3.31.10.2.1

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

OHO

OH

NH C C CH CH O2 P

H HCOO

NH2

COO

6.3.5.3 6.3.2.6 4.3.2.2

GuanineDNA

6.3.4.44.3.2.2

CCO

CCH

HCNH

N

N

HN CCO

CCH

HCNH

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

2.7.4.62.7.4.32.7.4.4

2.7.4.6

2.4.2.15

1.1.1.205

6.3.4.16.3.5.2

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

Glutamicsemialdehyde

2-AMINO ACID

Pyrroline-5-carboxylate

GlyoxylatePyruvate

4-Hydroxy-2-oxoglutarate

4-Hydroxy-glutamate

3-Hydroxy-pyrroline-

5-carboxylate

PutrescineH NCH CH CH CH NH2 2 2 2 2 2

Spermidine

Spermine

N -Trimethyllysine66N -Trimethyl-3-OH-lysine

Carnitine

Glutaryl-CoA Saccharopine2-Aminoadipatesemialdehyde

2-Aminoadipate2-Oxoadipate

Arginino-succinate

Guanidoacetate

Methylmalonyl-CoA

4.1.2.12

AspartylSemialdehyde

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

2.6.1.17N-Succinyl-2, 6diaminopimelate

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

CH3CH CH(OH)CHCOSCoA3

CH3

C(OH)CH(OH)COOCH CH3 2

CH3

CH = CCOSCoA2

CH3HOCH CHCOS-CoA-2

CH3

CH CHCO-SCoA3

CH3

C (OH)CH(OH)COOCH3

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

1.1.1.85Oxoleucine

COOH

(CH ) CHCHCH(OH)COO3 2

S-Adenosylmethylthiopropylamine

(Decarboxylated SAM)

PROLINE

Coenzyme A

CH C= CHCH3 2

CH3

OCH

CH

3

3HO

CH3CH3

CH3

CH C-CH H O3 2 2C PP

CH2

CH C= CHCH O2 2 PP

CH3

3-P-Glycerol

Phosphatidylethanolamine

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 2.7.7.42.7.1.251.8.99.1Adenylylsulphate

(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 2 NHCH CH CO2 2OCH C(CH ) CH(OH)CO2 3 2P

ADP- NHCH CH SH2 2 NHCH CH CO2 2OCH C(CH ) CH(OH)CO2 3 2

P-ADP- NHCH CH SH2 2 NHCH 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

2.1.1.102.1.1.20

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

NO1.14.13.39

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

2.3.1.512.3.1.15

2.7.8.5

SO -42

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

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

2.4.1.682.4.1.69

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

4.2.1.52

1.2.1.18

4.2.1.18

O

CHC

CHOCN

HN

DP

CHCO

CHOCN

HN

RPPP

OCH2

H

C C

H

OHOH

CH

NHNCH

CP

H

O

OCH2 C C

H

OH

H

OH

C

H

C CCNH2

CCH

HCN

RP(PP)

N

N

N+

P

NH2H

O

OCH2 C C

H

OH

H

OH

C

H

C COC

CCH

HCN

RP

N

N

NHP

H

OCH2 C C

H

OHOH

CO CH2 C

CONH2

CCH

HCN

RP

N

N

NHP

+OOCCH N(CH )2 3 3

Betaine

Betainealdehyde

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

6.3.2.136.3.2.7-10

2.7.7.27

2.7.7.9

3.5.4.10

CCO

CCH

OCN RP

N

NH

HN

CCO

CCH

N

N

N

HN

RPH 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

4.1.1.15

2.6.1.19

4.2.1.16

Carnosine

CH CH NH2 2 2C

NHNC

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

OHOH

HO OPPU

COO-

OH

H OH

HOCH2 C C CO

H

CO COO-

OCHOHCHOHAcNH

HO

OPC

OCO -CH OH2

OCHOHCHOHAcNH

HO

OH

COOCH OH2

O

OHOHHOHO

CH O2 P

O

OHACNH

HO OH

CH O2 P

O

OOHHOHO P

CH OH2

O

OHOH HOHO

CH OH2

O

OHHO OH

3

CH O2 PO

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 OH2O

OHO

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 OH2POCH2

H

OH OH

C C CO

H

HOCH2 CH OH2

OH

H OH

C C CO

H

HOCH2CH 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 PCHOHCOOPPOCH2

CHOHPOCH2 COO

COO

OH

OHOOH

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-CoACH 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 2NH3+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 CH 2 COO(NH )3+

OHOH

CH CH 2 COO-(NH )3+

CO

NH2

CH CH(NH )COO2 3+

NHOC

CO

NHOC

NH

CH

H N2

HCCH

N

N

C

RPH N2

CHC

CHOCN

N

DP

NH2

RPPP

CHC

CHOCN

N

NH2

CC

CCH

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

NHNC

HC

H

CH CH(NH )CH OH2 3 2

+C

NHNC

HC

H

CH CH(NH )CH OP2 3 2C

NHNCH

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

CO

C-COOOCN

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-CH3CO

CHOCN 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

CHCH

CH2

H C3

H C3H C3

HC

C

C

H

H

Fe

CH2

CH2

COO- -

CH3

CH3

CH2

CH2

CH2

H C3

H C3N

H

NH

NH

NH

CH

CH

H C2

C

CH2

H2

-

CH2

CH2

COO

CH2

CH2

COO -

H C2

H C2

CH 2

CH 2

OOC

COO

H N2

NH

-

-

CH2

H C2

H C2

H C2

H2

H2

CH2

CH2 CH2

CH2

CH2

CH2

NH

NH

NH

NH

COO

COO

COOCOO

C

C

--

CH2

CH2

COO

CH2

CH2

COO- -

-

-

OOC-

OOC-

CH3

CH3

H C3

H C3

H C2

H2

H2

NH

NH

NH

NH

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 CNH 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 C2NH

NH

CHCOO

CH2CH2

CH2

OOCCH(OH)CH COCOO2

NCHCOO

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+ +

CH2CH

OOCCN

HCCH-COO

CH2CH2

CH-COO OOCCN

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 3 OOCCH 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

+AdenosylSCH 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

NHNC

HC CH CHCOO2

NHCOCH CH NH2 2 2+

H

C

NHNC

HC CH CH(NH )COO2 3

CHCH CH COO2 2

NHNCH

OC C CH CHCOO

NHNCH

CH

CH COO3

NH

OOC

CH-COOOCNH2 CH2

H NCH CH COO2 2 2

H NCH2 2

CH3CHCOO H NCONHCH CHCOO2 2

CH3

CCO

CH

RPHC N

N

N

HN

C

CCO

CHHCO

N

N

N RP

CCH

N

NH N2

HC

CCO

CH

N

NC

CCH

N

N

RP

H N2

H N2C

O

O

O P~ ~P O

O

O O

P O

O

CH2

N

N

N

N

O

OHOH

NH2

HCCHN

N

N

N O

O

P O O

O

CH2

OH

NH2

HCCH

COOCO

NHOC

NH

CH

H N2NH2

OOC-CH-CH COO2

HNCO CCH

N

N

C

RPRPH N2

OOCC

CH

NRP

N

CH N2

CH=CHCOO

OH

CH=CHCOO

CH COCOO2

CH2

P

COO

OHO

O

O

COO

O

CH COO2OCH COO2-OOC

OCH2 CH2

OHHC

P

HOCH HCOH

OCCOO

COOHO

OHOHO

NH2COOOCH

NH

CH COCOO2NH

CHO

CO

NH2OH

CH CH(NH )COO2 3+

N

COOCOO

N+

COOCOO

RP

O

OH

OH

HO OPPU

COO

O

OH

NHCOCH3

HO

OPPU

COOCH OH2

O

OCCH2 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

COOHO 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

NRibose - O - P - O - P - O -Adenosine

O

O

O

O

II

IIOH

O

CH CH 2 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

++

HOH

HOH

HHO

HHO

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-OCHCH 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

NHNC

HC

H

CH CH(NH )CHO2 3

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-Ribulosylformimino5-aminoimidazole-carboxamide-R P

Imidazoleacetol-P

HS HSO-

PANTOTHENATE

3-Isopropyl-malate

Succinicsemialdehyde

2.4.1.17

Diacylglycerol

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

2.4.1.1etc.

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-Gluconolactone

1.1.1.44

O

OOHHO

OH

CH O2 P

PHENYLALANINETYROSINE

TRYPTOPHAN

INOSINE-P(IMP)

THYMIDINE-P

HISTIDINE

URIDINE-triphosphate

(UTP)

CYSTINE CYSTEINE

ISOLEUCINE

LEUCINE

LYSINE

ORNITHINE

ARGININEHYDROXYPROLINE

PHOSPHATIDYLSERINEPhosphatidyl

inositol

LECITHIN

SPHINGOMYELIN

STEROIDS

Pregnenolone

2.7.6.1

2.4.2.146.3.4.7

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

2.7.1.362.7.4.2

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)

TriacylglycerolFAT

RNA

CH3

CH2

OC-COOOH

COO

CH CH 2 COO(NH )3+

GLYCOPROTEINSGANGLIOSIDES

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-PO2O-

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

HOCH2CH 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

Malonicsemi-

aldehyde

2.7.2.4

2.1.3.3

3.5.1.26.3.1.2

6.3.

5.5

CarbohydratesBiosynthesisDegradation

Amino AcidsBiosynthesisDegradation

LipidsBiosynthesisDegradation

Purines &Pyrimidines

BiosynthesisDegradation

Biosynthesis DegradationVitamins Co-enzymes & Hormones

Pentose Phosphate Pathway

Photosynthesis Dark Reactions

COMPARTMENTATIONThe "Backbone" of metabolism involves

GLYCOLYSIS in the CYTOPLASM,the TCA CYCLE (mainly) in the Mitochondrial matrix

and ATP FORMATION spanning theMITOCHONDRIAL INNER MEMBRANE

An electron flow (an electric current) generated fromNADH 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 energyneeded to form ATP from ADP and phosphate

Electron Flow Proton Flow

Small Numbers ( eg. 2.4.6.7) refer to the IUBMBEnzymeCommission (EC) Reference Numbers of Enzymes

LEGEND

Human Metabolism is identified as far possible by black arrowsBiosynthesis Degradation

HEMOGLOBIN CHLOROPHYLL

ATP

TRA

NS

LOC

ATED PROTONS

2.7.1.1

ATP2.7.1.2

Metabolic PathwaysMetabolic Pathways

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22nd Edition Designed by Donald E. Nicholson, D.Sc., The University of Leeds, England – and Sigma-AldrichProduct No. M 3907

XXX