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CONH 2 COO
HYALURONIC ACID DERMATAN BLOOD GROUP ALGINATES O-ANTIGENS STARCH GLYCOGEN + O O + O O COO
P GLYCOPROTEINS SUBSTANCES CH2COO OH N
Ribose -O - P - O - P - O- Adenosine(P)
N
Ribose - O - P - O - P - O -Adenosine + NICOTINATE COO COO
1.4
E (Sialate)
HO O OPPU UDP-
O
2.7.7.13 MANNOSE 4.2.1.46
+
CH2CH(NH 3)COO
COO
1.2.1.32 I
.1
OH C-CH(OH)CH(OH)CH 2OP HOC-CH(OH)CH(OH)CH 2OP NH C C CH CH2OP
CH2 C 2 Galactose-P CH2CH 2NH2
.1
COO COO
S CH2OP NHAC Galacturonate 1.1.1.2
N
9
2.7.1.7 2.7.7.27 CH CH OH OH 1.14.12.1
COO O HO OH HO O P CH 2OH NH N NH2
O NH 4.2.1.20 N O
H H 2.4.2.18 OOC NH 2
UDP-N-Ac- 5.1.3.7 Mannose-1-P 2.7.7.34 O
Tryptamine
4.1.1.28
Indole-3-glycerol-P 1-(o-Carboxy phenylamino)
4.1.1.48
N-(5-P-Ribosyl) Anthranilate O
ACNH
HO OH
3.1.3.29
4.1.3.20 Glucosamine HO OH OPPU 5.1.3.6 CH 2OP
O
TDP-Glucose 2.7.7.9 5.1.3.2 HO
COO
TRYPTOPHAN 1-deoxyribulose-5-P anthranilate
OOC
2-Amino
OH 2.7.7.10
pyruvate OH 2.7.7.12 OH OPPU OC
HO COO COO COO OOC
muconate
N-Ac-Mannosamine-6-P
CH2OH
UDP-Glucuronate
CH2OH
5.4.2.8
HO OH HO OH
2.7.7.24 CH 2OH
O OH P OCH 2 CH2 COO COO
COO
4.1.3.27
CH 2COCOO
A
CH2OP
CH2OH
O O 4.1.3.20 O O
HOCH HCOH
C OH OH HO OH
CH2
O-C-COO
CH2
C
P O OH P O
H 2.7.1.60 Mannose-6-P 2.4.1.13 CH 2OP HO OH OP UDP-Galactose H OH
4.6.1.3
O OH
4.2.1.10
O
OH
1.1.1.25
OH
2.7.1.71
OH
2.5.1.19
OH OH OC-COO
5.4.99.5
OH I
Shikimate-5 4.6.1.4
ACNH
HO OH OH HO OH OPPU HO OH OP HO OH OH
O HO 3-Deoxy-D-arabino- Dehydro- Dehydro- Shikimate Shikimate-3-P Chorismate Prephenate D
E 2.4.1.9
heptulosonate-7-P quinate shikimate PEP
enolpyruvate 3-P
X
NHAC NHCOCH 3 5.4.2.3
N-Ac-Glucosamine-6-P
NHCOCH 3 Glucose-1-P O O
OH CH2COCOO
+
CH2CH(NH3) COO
+
CH2CH(NH3) COO S
N-Ac-Mannosamine UDP-N-Ac-Glucosamine N-Ac-Glucosamine-1-P HO OH OH CH2OH
O CH2COO
CH2COCOO
4.2.1.51
5.1.3.14 2.7.7.23 2.3.1.4
O COO OH OH OH H H OH
NH2
-OOC
O
CH2COO
O
CH2COO
1.3.1.13
OH
S 5.3.1.8 Glucosamine-6-P HO OH OH
COO OH OH OH
Fumaryl 5.2.1.2 Maleyl 1.13.11.5 Homogentisate
O C C C CO CH2OH 1.13.11.27 2.6.1.5 1.14.16.1 2.6.1.5
OH OP
HOCH 2 Hydroxyphenyl TYROSINE PHENYLALANINE Phenylpyruvate
E OH H OH OH
OH OH H OH
acetoacetate acetoacetate pyruvate 4.3.1.
5
COO -
1.3.1.13 1.3.1.13
HOCH 2 C C C C HO OH HO OH 3.2.1.26
S H OH H H
HO OH OH
OH
Fructose SUCROSE 3.2.1.48
GLUCOSE CHOHCH 2NHCH 3 CHOHCH 2NH2 CH2CH2NH2 CH2CH(NH3) COO-
+
OH OH 4.1. CH2CH2NH2
1.1.1.19 1.13.99.1 3.1.3.25
Gulonate Glucuronate Inositol Inositol-P 5.5.1.4
1.25 CH=CHCOO
C
OH H OH OH OH H OH 1 5.4.2.2 OH OH OH OH Ubiquinone Cinnamate A
3.1.1.18 HOCH 2 C C C C CO HOCH 2 C C C CO CO
OH H OH OH 1.1.1.2 ATP OH OH OH OH
1.14.16.2
Menaquinone
H H H H H
HOCH 2 C C C C CO 1.1.1.14 H H OH H CH2OP
O
3.1.3.9 2.7.1.2 Epinephrine 2.1.1.28
Norepinephrine 1.14.17.1
Dopamine 4.1.1.28
Dopa CH2CH(NH3) COO
+ OH
Tyramine 1.14.13.11 T
2.7.1.1 (Adrenaline) (Noradrenaline)
O O H O HOCH 2 C C C C CH2OH
2.6.1.16
ADP CHOHCH 2NH2 HN O E
Gulonolactone 1.1.3.8 2-Oxogulonolactone ASCORBATE OH OH H OH O 1.6 1.14.18.1 I I CH=CHCOO
1.10.2.1 2.7 HO OH CH2 OP 2.1.
H2
C
1.1.1.45
OH H OH OH H OH H
1.10.3.3 Sorbitol .1.4 1.1.1.49 O OCH 3 α-Tocopherol O C
O Coumarate
HOCH 2 C C CO C COO- HOCH 2 C C CO CO COO - HOCH2 C C CO CO CO OH CH(OH)COO OH CHOHCH 2OH (Vitamin E)
CH-COO O
H
H OH H H OH H O 2.7.1.3 P-Glucono Glucose-6-P Normetepinephrine O
+
NH3 O
OH
O
1.1.1.130
P 3-Dehydrogulonate 2, 3-Dioxogulonate Dehydroascorbate H H OH H 3.1.
1.17 lactone HO OH OH
OH
OCH 3
3.4
(Normetadrenaline) OCH 3 Dopaquinone
O NH
I
OH
I
L
E POCH2 C C C C COO - NADP + OH 1.4. OH
1.14.18.1
OH H OH H H OH H H
5.3.1.8 5.3.1.9 4-OH-3-Methoxy- 4-OH-3-Methoxy- Plastoquinone MELANIN THYROXINE LIGNIN Tannins Plant Pigments A
N OH OH H OH
6-P-Gluconate NADPH
HOCH 2 C C C CHO HOCH 2 C C C CHO HOCH 2 C C CO CH 2OH
H H OH
D-mandelate phenylglycol M
T H OH H OH OH H
5.3.1.3
OH OH
2.7.1.47 HOCH 2 C C C CO CH2OP NADP + CH2OP
OOC-CH-CH 2COO I
4.1.1.34 D-Arabinose D-Ribulose
O L-Xylose OH OH H 1.1.1.44
H H HO O NHCOCH 2NH2 NH NH N OOC N
HNCO C N
O N
S OH H H OH H OH H
Fructose-1-P 2.2.1.1 POCH2 C C C CO CH2OH H 2C CHO H 2C CHO
HC
CH
C
CH CH H 2N
C
C CH
N
C
E HOCH 2 C C C CH2OH HOCH 2 C C CO CH 2OH POCH2 C C CO CH2OH
H H H NADPH
OH OH H
OH OH
OC
NH
RP
HN C
NH
RP
H 2N C
N
RP H2 N
C
N
RP
H 2N
N
RP H 2N
C N RP E
H OH OH H OH
2.7.1.53
H OH 5.1.3.1 Fructose-6-P Glycinamide- 2.1.2.2 Formyl 6.3.5.3 Formyl 6.3.3.1 5-Amino 4.1.1.21 5-Amino-4-imidazole 6.3.2.6 5-Amino-4-imidazole 4.3.2.2 5-Aminoimidazole O S
S L-Arabitol L-Xylulose L-Xylulose-5-P HOCH 2 C C C CH2OH H H
ribosyl-P glycinamide-R P glycinamidine-R P imidazole-R P carboxylate-R P (N-succinylcarboxamide)-R P carboxamide-R P C C N
OH OH H H OH H H OH H OH OH OH
Ribitol
POCH2 C C CO CH2OH ATP H2 N
HCO C
CH
*
.4.1 2.4.2. HN C
P 2.2.1.1
+
d-ATP 2.7. 1 6.3.5.2 CH
PQ 2e-
2e- H+ OOCCH2N(CH3)3
7.7 d-CTP H2 N C C
H 2e-
PQH2
PQ .
_
POCH 2CHOHCHO
Betaine FOLIC ATP 2.7.7.6
RNA 2.7.7.6
GTP 2.7.4.6
GDP 2.7.4.8
N N RP
O QB 1e- 1e-
PQ
3-P-Glyceraldehyde 2.1.2.1 ACID 2.7. GUANOSINE-P
NADP+
H+ 1.2.1.8 1.17.4
Fe-S HOCH2COCH2OP
2.2.1.1 7.6 TTP 2.7.
T PQH2 Cyt bf
Dihydroxy- 1. 1 + C1 4.6 .1 (GMP)
QA A1 H+ 5.3. 2.4.2.14 OHCCH 2N(CH3)3
O 2e-
H+ acetone-P Pi 6.3.4.7 Betaine POOL O
NH2
P
S Pheophytin Cyt bc Chl.A0 1.1
Pi 4.2.1.2
0 O O 2.7. TDP O C
NADPH+H+
C CH
(Glycerone-P) 5.3. aldehyde 4.1.2.5 C 7.6 C N
Y
._ NAD+
2e- HN CH-CH3 C
C CH3
2.7. HN C-CH3
HN CH
4.9 CH
Y P680 2PQH2
2PQ 2PQ 2.7.1.28 CH3
CH3
OC CH 2
HN
OC CH 2.1.1.45 OC CH
OC
N
R
N Chl.a
2e- PC
P700 Pi ADP +
1.1.99.1
H2NCH 2 CHCOO H2NCONHCH 2CHCOO NH
OC
NH
CH
2.4.2.4
N
DP N DP
3.5.4.12 2.7.4.14
DP
2e- H+
Glyceraldehyde
HOCH2CH2N (CH3) 3
O
α
M
α
1.2.1.13 + O NH 2
1
Pi 2.4.
H 4H+ HOCH2CH(NH3)COO 2.1 C C 2.4 C
a
4.2.1.22 CH2
H+ H+ H+ NADH HN HN CH
8
.1.1
β
H2O
N CH
Translocated protons ADP 1.17.4.1
I
8
SERINE
2
E H+
CO2
β
3 OC CH2 OC CH
1
OC CH
H+ H+ CH2OP 2.6.1.51 4.1.1.11 H2NCONHCH 2CH 2COO N H
H+Protons from Water
NH
H+ H+ H+ H+ H+ H+ H2NCH 2CH2COO
D
3
NH
S
3
εε
H+
1:3-bis-P-Glycerate
2
c
H+ H+ 2.7.6.1
H+ H+ H+ H+ H+ H+ β2 HOCH2COCOO O
H+ -OOC O O C
CH 2.7.4.6
α
α
OP O P O O C
H+ 3.1.3.3 N
S H+
Hydroxy- NH2 CH2 C C C
CH C HN CH N
ATP
3
H+
OH OH HN HN CH HN OC CH
ATP pyruvate OC CH-COO 2.4.2.9 OC CH N
THYLAKOID MEMBRANE P-Ribosyl-PP + N
H
OC
NH
CH-COO OC
NH
C-COO OC
N
C-COO
RP
OC N CH
RP
N
RPPP RPPP E
ADP ADP P OCH2CH(NH3)COO 6.3.4.2
S
STROMA 3.6.1.34 Phospho- Carbamoyl Dihydro Orotate Orotidine-P Uridine-P UDP URIDINE- CYTIDINE-
3.5.2.3 4.1.1.23 (UMP) 2.7.4.4
CHLOROPLAST OUTER MEMBRANE 2.7.2.3 serine aspartate orotate 1.3.1.14 2.4.2.10 2.7.4.6 triphosphate triphosphate
1.1.1.29 (UTP) (CTP)
HO HO
COO COO ATP 2.6.1.52
2.6.1.22
NH2 NH2
COO H H H H H H H H H H CONH 2
+ C N OC N N H H
γ-Linolenate
1.14.99.25 P OCH2 C C C C N C P OCH 2 C C C C NH C P OCH 2 C C CO CH2 NH C
Linoleate Arachidonate 1.13.11.34 Leukotriene B4 OH
POCH2CHOH COO
1.1.1.95
P OCH2COCOO
HC C
CH
HC C
CH
HC C
CH
P OCH 2 C C C CH
COO 5.3 O
3-P-Glycerate P-Hydroxy- OH OH
N N OH OH
N N OH OH
N N OH OH HN N
1.1 .99 COO COO O RP(PP) O RP RP
1.3.1.35 4.9 .3 pyruvate 3.6.1.31 3.5.4.19 C
9.1 O 2.4.2.17
P-Ribosyl-ATP P-Ribosyl-AMP P-Ribosylformimino P-Ribulosylformimino Imidazole H
COSCoA
L CO-S-ACP
HO OH 5.3.99.5
HO
OH 2.7.1.31 5-aminoimidazole- 5.3.1.16 5-aminoimidazole- glycerol-P
HC C CH 2CHCOO
I Oleoyl-CoA Palmitoleoyl-ACP Prostaglandin PGE 2 Thromboxane B2 POCH2CH(O P) COO + carboxamide-R P +
carboxamide-R P+
1.14.99.5 HOCH2CH(OH) COO N NH NHCOCH 2CH2NH2 HC C CH2CH(NH 3)COO + HC C CH2COCH2OP
2, 3-Diphospho- 5.4.2.1 HC C CH2CH(NH 3)CHO HC C CH 2CH(NH 3)CH2OH HC C CH2CH(NH 3)CH2OP
4.2.1.19
P COSCoA CH3(CH2)14CH=CHCOS-CoA CH3(CH2)14CH(OH)CH 2COS
COS-CoA CH3(CH2)14COCH 2COS-CoA
glycerate Glycerate C
H Carnosine N
CH
NH
N NH N NH N NH
N
C
NH
H R'-CO-OCH O
O O O- aldehyde 1.1.1.37
- 2.1.3.1 6.4.1.3 COOH COOH +
+ Cardiolipin Phosphatidylglycerol 1.4.3.8
CH3C(OH)CH 2CHO
FMNH2 2COO
4.1.1.41 (CH3)2CHCH 2 CH(NH 3)COO
ADP- OCH2 C(CH 3)2CH(OH)CONHCH 2CH2CO NHCH 2CH2SH
O CH 2O P OCH 2CH2 NH 3
O-
+ + Mevaldate ISOCITRATE 5.1.99.1
(CH3)2CHC(OH)CH 2COO (CH3)2CHCHCH(OH)COO (CH3)2CHCH 2COCOO 2.6.1.6
LEUCINE Dephospho-Coenzyme A
CPP- OCH 2CH2 NH3 POCH2CH2 NH3 + + 2-Isopropyl- 3-Isopropyl- 1.1.1.85 Oxoleucine
S 2.7.8.1 CDP-Ethanolamine 2.7.7.14
Ethanolamine-P 2.7.1.82 HOCH 2CH 2NH 3 2H 4.1.3.1 1.1.1.41 CH3 malate 4.2.1.33
malate 1.4.1.9
Phosphatidyl Ethanolamine 1.1.1.32
2Fe -S CH3CH(OH)CH2CO.SCoA
2.7.1.24
P ethanolamine
CH2OH
(5 Clusters) OOC-CH-COSCoA CH3 CH3 1.2.1.25
CH2O-CO-R MALATE 4.2.1.18
H CEPHALIN
HOCH O CH 3COCH 2CH 2N(CH 3)3 -OOCCOCH - Methylmalonyl-CoA OOCCH 2C = CHCOSCoA CH3C = CHCOSCoA (CH3)2CHCH 2COSCoA P-ADP- OCH 2 C(CH 3)2CH(OH)CONHCH 2CH 2CO NHCH 2CH2SH
4H+
+ 4.1.1.71
4H+
2CH2COO
O
HOCH O
+ CH2OPO CH2CH 2N(CH 3) Acetylcholine CH C(OH)CH
2 CH COO
2-OXO- 3-Methyl-
6.4.1.4
3-Methyl-
1.3.99.10
Isovaleryl-CoA A
CH2OPO CH2CH2N(CH 3)3 O- 2 CH2OH 1.6. 5.3 ASPARTATE 2.7.2. 4.2.1.18 Coenzyme A
L CH2OCH=CHR
2.1.1.17
2.1.1.71 O - Lysolecithin 3.1.1.5 Glycerophosphocholine 3.1.
4.2
3
Mevalonate 2H+ 4.2.1.2 GLUTARATE 4
1.1.1.3
glutaconyl-CoA crotonyl-CoA M
I R-CO-OCH O
CH 2 O-CO-R
3.1.1.32
3.1.4.4 2.3.1.6 or 1.2.4.2
2.3.1.61
I
2H+ -
+ R'-CO-OCH O 3.1.4.3 2.7.1.36 +
P ß-CAROTENE (C40) 2.5.1.32 2.5.1.29 CH3C= CHCH 2 CH2C= CHCH 2OPP Cyt.bL Cyt.bH MI (Decarboxylated SAM)
A
R Metarhodopsin Rhodopsin O
CH2OPP Geranyl-PP NA
TIO N GLUTAMATE 2.7.2.1 +
2.5.1.22 Carbohydrates Amino Acids
CH3 (C10) Cyt.c1 1 POOCCH2CH 2CH(NH3) COO Biosynthesis Biosynthesis
1.13.11.21
E COO- Opsin
CH3O Geranyl-geranyl-PP
(C20) Glutamyl-P
H2N(CH 2)4NH (CH2)3NH2
Degradation Degradation
CH3O n
2UQ UQ Spermidine
N O Ubiquinone 2.5.1.10 1.10.2.2
Retinoate 1.4.1.14 3.5.1.2
O 1.2.1.36
CHO (Coenzyme Q) OPP Cyt.c 1.4.1.2
6.3.1.2 1.2.1.41
Lipids Purines &
5.2.1.3 CH2 2.5.1.16 Biosynthesis Pyrimidines
I trans-Retinal 11-cis-Retinal CHO Menaquinone CH2OH
D
Light Phytol (C20) or ting ATP NO3- NH4 + + Degradation Biosynthesis
1.1.1.105 1.1.1.105 nsp 3.6.1.34 synt H2NOCCH 2CH2CH (NH3) COO + H2NCH2CH2CH2CH2NH2
Retinol esters Plastoquinone CuA CuA +-
tra h 1.6.6.1
7.1 Glutamine OHCCH 2CH 2CH(NH3) COO
Putrescine Degradation
S CH3 1.7.99.4 1.7. 6.4 ATP Glutamic
as
O Farnesyl-PP oscp
H
HO
1.6. .1
e
CH 3
2H+ semialdehyde
2.3.1.76
3.1.1.21
CH2OH CH 3 O (C15)
Heme a NO2- 8.6 6.3.4.16 CO2 Vitamins Co-enzymes & Hormones
1.1
CH2OH CH3 CH3COCOO OHCCOO Biosynthesis Degradation
S 5.2.1.7 6.3.5.5
.5
CH2 CH2
trans-Retinol 11-cis-Retinol O
Phylloquinone α-Tocopherol
.5
Dark
T (Vitamin A) (Vitamin K) (Vitamin E) F6 N2
H2NCOOP 2.6.1.13
CH CHCOO
Pentose Phosphate Pathway
N
E STEROIDS 2H+ CuB Heme a3 2H+ ATP Carbamoyl-P +
H 2NCONHCH 2CH2CH2CH(NH3) COO Pyrroline-5-
R β
2 ATP CITRULLINE carboxylate
4.1.3.16
Photosynthesis Dark Reactions
2e- γ
O 3
β
OOCCH(OH)CH 2COCOO
AD
H
I HO
H
HO
H 1.9.3.1
P +1 P i AαT 1.5.99.8
CH2 CH2
4-Hydroxy- Human Metabolism is identified as far possible by black arrows
HO HO α
Pi 2.1.3.3 1.5.1.2 2-oxoglutarate
IV ADP +
H
1/ O Biosynthesis Degradation
D Pregnenolone CHOLESTEROL Desmosterol Zymosterol
H
Lanosterol 5.4.99.7
Squalene 2 2 H+
H+
+
H2NCH2CH2CH2CH (NH3) COO
CH2 CHCOO
1.14.99.7
S (C30) H+ β
F1 ORNITHINE
NH
2.6.1.23 COMPARTMENTATION
H+ γ 6.3.4.5
PROLINE
HEMOGLOBIN CHLOROPHYLL COO- H2 O
H+
+ The "Backbone" of metabolism involves
COO- 1.14.11.2 OOCCH(OH)CH 2CH(NH 3)COO
COO- ε H2NCONH 2 OOCCHCH 2COO GLYCOLYSIS in the CYTOPLASM,
P CH2
CH3
CH2 CH2
COO- CH2 COO-
COO- CH2
δ F0 2.1.4.1 UREA N + HOCH CH2
4-Hydroxy- the TCA CYCLE (mainly) in the Mitochondrial matrix
CH CH
O H H2 CH3 CH CH2 H2 CH3 H2NCNHCH 2CH 2CH2CH(NH3) COO glutamate
TRA N S L O
N N N N N N
N
H H
N
-OOC
CH 2 E D PROTONS H+ H+ ARGININE PROLINE pyrroline-
The retrolocation of these protons through the F0 subunits
Y H3 C
C
CH3 H3C
C
CH3 H3C
C
CH3
H 2C CH2 CH 2 4.2.1.24 H+ H+ of ATP synthase to the matrix then supplies the energy
H - C H2 C
ADP Pi 4.3.2.1 5-carboxylate needed to form ATP from ADP and phosphate
R CH2 CH2 CH2 H2 CH2 CH2 H2 CH2 OOC CH2 H2 CH2
COO-
+ NH + NH2 + NH2 HN C
NH CO
Electron Flow Proton Flow
I CH2
COO-
CH2
COO-
CH2
COO-
CH2
COO-
CH2
COO-
CH2
COO-
CH2 CH2 H2 C N
H X ATP Y H2NCNHCH 2COO
2
H2NCN(CH 3)CH2COO P- HNCN(CH 3)CH2COO
N CH 2
1.5.1.2
COO- COO-
N 4.1.1.37 4.3.1.8
H2 N
Guanidoacetate
2.1.1.2
Creatine 2.7.3.2 P-Creatine
CH3
Small Numbers ( eg. 2.4.6.7) refer to the IUBMBEnzyme
1.3.3.4 1.3.3.3 Creatinine
S HEME Protoporphyrinogen Coproporphyrinogen Uroporphyrinogen Porphobilinogen E NDE
RGONIC REACTIO N 3.5.2.10 Commission (EC) Reference Numbers of Enzymes
4.99.1.1 4.2.1.75
© 2003 International Union of Biochemistry and Molecular Biology 22nd Edition Designed by Donald E. Nicholson, D.Sc., The University of Leeds, England – and Sigma-Aldrich
Product No. M 3907
www.iubmb.org
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