Mapa Metabólico

Prévia do material em texto

2H+
H+
 OXA L OA C E T A T E
P Y R UV A T E
S UC C INY L -C oA
 
G L UT A R A T E
C IT R A T E
MA L A T E
2-OXO- A S P A R T A T E
NO2
-
NO3
-
N2
NH4
CH3COSCoA
 A C E T Y L -C oA
HOH
C O2
NA D
T
R
A
N
S A MIN A T IO N
2H+
2H
+
+
C O2
5-A mino-
levulinate
Glycine
H+
H+
H+
H+
H+
H+
c
H+ H
+a
F 0
F 1
F 1
β
2
1 α
β
α
γ
10 c-s ub-u
nits
A
D P+ Pi
H+
3.6.1.34
 
 
H
+ -t
ran
spor
ting AT P synthas e
α
δ
F 6
oscp
AT P
ADP +
 P i
F UMA R A T E
UQH2
UQ
UQH2
NA DH+H+
CH2COO-
C(OH)COO-
CH2COO-
CH(OH)COO-
CHCOO-
CH2COO-
-OOCCOCH2CH2COO-
-OOCCH2CH2CO.SCoA
-OOCCOCH2COO-
CH3CH(OH)CH2CO.SCoA
-OOCCH=CHCOO-
Glyoxylate
 Cycle
-OOCCHO
GTP
GDPATP
+
HE ME P rotoporphyrinogen C oproporphyrinogen Uroporphyrinogen P orphobilinogen
5-A mino-
levulinate
COO-
CH2
CH2
H2NCH2C=O
F ADH2
F ADC yt.b
F e-S 
S UC C INA T E
II
CH3COCOO-
P Y R UV A T E
P i
X Y
C yt.c1
F e-S 
2e-
2e-
1e-
1e-
III
2UQ UQ
UQH22UQH2
2UQ.
_
 UQ.
_
C yt.bL C yt.bH
C yt.c
IV
C uA
C uB
C uA
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
IS OC IT R A T E
2.6.1.1
2.3.1.16
4.1.1.71
1.2.1.16
5.1.99.1
5.4.99.2
4.3.1.1
1.4.1.2 1.4.1.14
6.3.5.4
1.6.6.1
1.7.99.4 1.7
.7.1
1.6
.6.4
1.1
8.6
.1
2.3.1.37
1.10.2.2
1.10.2.2
γ
εδ
β
33 β
A T
P
A DP
E NDE R G ONIC R E A C TIO
N
1
.6
.5
.3
I
F MNH2
F MN I
1.6. 5.3
2F e -S 
(5 C lusters )
H+ H+
H+ H+
ATP
4H+
2H+
2H+
or
H+
PHOTO-
SYSTEM
l
O2
3.6.1.34
NADP+
Glyceraldehyde
Ribulose-1,5-bis-P
2β
8 8
H
+c
3
2
ε
a
3
2
α
1
α
ε
α
β2
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+
P i
Ferredoxin
4H+
PC PC
PC
PQH2
2PQH2
PQ
_.
2PQ
_.
Fe-S Cyt.f
PQ
2PQ
Cyt bf
2e-
1e- 1e-
2e-
2e-
2e-
2e-
Cyc
lic Ph
otophosphorylation
PQ
PHOTO-
SYSTEM
 II
 
Cyt bc
Non
-cyclic electron flow
2e-2e-
Mn
2e-
*
Protons from Water
H2O
H+
H+
2H+
2H+
γ
ATP synthase
CO2
Fixation
H+
 ADPPi
H+
NADPH+H+
 ATPTHYLAKOID MEMBRANE
CHLOROPLAST OUTER MEMBRANE
THYLAKOID LUMEN
STROMA
 (electric current)
P680
Chl.a
QA
QB
Pheophytin
P700
Chl.A0
A1
Fe-S
A T P
A DP
A T P
1/2O2
H2O
PQH2
T o B rain - 
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
V IS ION
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
C O C H C H(NH )C OO2 3
+
F OL IC
A C ID
C 1
P OOL
V A L INE
A T P
A T P
4.1.1.4 1.1.1.30
C H C OC H3 3
C H C OC H C OO3 2
C H C H(OH)C H C OO3 2
3-OH-B utyrateA c etone
A c etoac etate
K E TONE B ODIE S
HY A L UR ONIC A C ID DE R MA T A N B L OOD G R OUP
S UB S T A NC E S
P E P T IDO-
G LY C A N 
N-A c -Neuraminate
(S ialate)
UDP -
Iduronate
UDP -N-A c -
G alac tos amine UDP -
G alac turonate
G DP -F uc os e
T DP -R hamnos e
A DP -
G luc os e
UDP -G luc os e
T DP -4-Oxo-
6-deoxygluc os e 
MA NNOS E
C HIT IN C HONDR OIT IN P E C T IN
A L G INA T E S
INUL IN C E L L UL OS E
O-A NT IG E NS S T A R C H G LY C OG E N
L A C TOS E
G A L A C TOS E
O
OH
HO
OH
OH
C H3 O
OP P T
O
OH
OH
O
OH
AC NH
HO OH
O
OHHO OP P U
NHAC
OH
OH OH
OH
HO
OH
NHC OC H
OH HO
O
OP P G
C H OH2
HO
P
UDP -N-A c -
G luc os amine
pyruvate
N-A c -Mannos amine-6-P UDP -G luc uronate
G DP -Mannos e 
N-A c -Mannos amine UDP -N-A c -G luc os amine N-A c -G luc os amine-6-P
S orbitol
F ruc tos e-1-P
E rythros e-4-P
3-Dehydrogulonate
L -Xylos e
L -L yxos e
D-Xylulos e
D-R ibos e
R ibitol
L -A rabitol L -Xylulos e
L -R ibulos e L -R ibulos e-5-P
L -Xylulos e-5-P
L -A rabinos e Xylitol D-Xylos e
D-A rabinos e D-R ibulos e
A S C OR B A T E
2, 3-Dioxogulonate
N-A c -G luc os amine-1-P
Inos itol-PInos itolG luc uronateG ulonate
G ulonolac tone 2-Oxogulonolac tone
F ruc tos e
6-P -G luc onate
D-R ibulos e-5-P
D-Xylulos e-5-P
Mannos e-1-P
G DP -G luc os e
T DP -G luc os e
UDP -G alac tos e
G alac tos e-P
G luc os e-1-P
G luc os e-6-P
F ruc tos e-6-P
F ruc tos e-
1: 6-bis -P
OH
H H H
O
HOC H 2 C C C C C O
OH OHH OH
H H
O
HOC H 2 C C C C O C O
OHH
H
OH H
C C
OH
C O
P -R ibos yl
amine
G lyc erate
2, 3-Diphos pho-
glyc erate 
3-P -G lyc eraldehyde
1: 3-bis -P -G lyc erate
3-P -G lyc erate
2-P -G lyc erate
P -enolpyruvate
Inos itol
C H OH2
C H OH2
HOC H
C H OH2
C H O2
HOC H
P
G lyc erol
UDP -G alac tos e
UDP -S ugars
C H C H OH3 2
E T HA NOL
Dihydroxy-
ac etone-P
(G lyc erone-P )
G luc os amine-6-P
P hos pho-
s erine
C hain elongation Mitoc hondrial
S erine
S erine
Indole-3-glyc erol-P
3-Deoxy-D-arabino-
heptulos onate-7-P
Indoleac etate
(A uxin)
Indoxyl
F ormylkynurenine K ynurenine 3-Hydroxy
kynurenine
3-Hydroxy
anthranilate
2-A mino-3-c arboxy
muc onate s emialdehyde
NH
OH
T ryptamine 1-(o-C arboxy phenylamino)
1-deoxyribulos e-5-P
N-(5-P -R ibos yl)
anthranilate
A nthranilate
C atec hol
NH
Indole-
ac etaldehyde 
NH
C H C HO2
Indolepyruvate
N
H
C -C H(OH)C H(OH)C H O2 P
C H
2-A minomuc onate-
6-s emialdehyde 
C H C H 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 2.5.1.19S hikimate-3-P S hikimate-5
enolpyruvate 3-P
C horis mate
P E P
2.7.1.71
1.4.1.19
Homogentis ate P henylpyruvate
C innamate
C oumarate
P rephenate
2-A mino
muc onate
F umarate A s partate
G LY C INE
S arc os ine
Hydroxy-
pyruvate
P -Hydroxy-
pyruvate
S E R INE
Imidazole
glyc erol-P
P -R ibos yl-A T P P -R ibos ylformimino
5-aminoimidazole-
c arboxamide-R P
F ormimino
glutamate
Imidazolone
propionate 
Uroc anate
C ys tathionine Homoc ys teine
P hos phoadenylyl-
s ulphate
(P A P S )
 C H (NH )C OOH2 3
+
His tidinol-PHis tidinolHis tidinal
3.1.3.15 2.6.1.91.1.1.23
3.6.1.31
5.3.1.162.4.2.17
A s paragine
A L A NINE
3-S ulphinyl
pyruvate 
Oxobutyrate
2-A c eto-2-
hydroxy-
butyrate
O-P hos pho-
homos erine
HO S C H C H NH2 2 2 2
Hypotaurine
HO S C H C H NH3 2 2 2
T aurine
G lutamate
γ-G lutamylc ys teine
G lutathione
G lyc ine
C ys teine
ß-A lanine
C ys teate
S -A denos yl
homoc ys teine
4.2.99.2
1.1.1.86
4.2.1.9
1.1.1.864.2.1.9
2.6.1.32
4.1.3.18
S -A denos yl
methionine
(S A M)
2-Methylac eto-
ac etyl-C oA
2-A c etolac tate 2-3-Dihydroxy
is ovalerate
2-Oxo-
is ovalerate
3-Hydroxy-
is obutyrate
3-Hydroxy-
Is obutyryl-C oA
Methyl
ac rylyl-C oA
2-Methyl-3-
hydroxy-
butyryl-C oA
T iglyl-C oA 2 Methylbutyryl-
C oA
2: 3-Di-OH-
3-methylvalerate
2-Oxo-3-methyl
valerate
Is obutyryl-C oA
C ys teine
s ulphinate
4.2.99.9
2-Is opropyl-
malate
C H C H C OC OO3 2
+
C H C H(NH )C OO3 3
C H C H(OH)C OO3
HO S C H C OC OO2 2
OC H C OC OO2P
OC H C H(NH )C OO2 3P
HOC H C OC OO2
HOC H C H(NH )C OO2 3
+
+
OH
C H C OC OO2
C OO
 OH
OHO
C OO
 OH
OH
HO P
C OO
 OH
OH
O
C H2
P 
C OO
 O-C -C OO
OH
O
OH
 OOC C H C OC OO2
N H
HOC -C H(OH)C H(OH)C H 2OP
C H
C OO
NH2
C OO
OH
NH2C OO
C OO
OC H
 OOC C H NHC H2 3
C H (C H ) C OS -AC P3 2 14 C H (C H ) C OS C oA3 2 14
C H (C H ) C H=C HC O-S -AC P3 2 2
C H C H=C HC O-S -AC P3 C H C H(OH)C H C OS -AC P3 2
C OS C oA
L inoleate
Oleoyl-C oA
S tearoyl-C oA Dehydros tearoyl-C oA OH-S tearoyl-C oA Oxos tearoyl-C oA
P almitoyl-A C P P almitoyl-C oA
A C Y L -A C P 2, 3-E noyl-A C P
3, 4-Dec enoyl-A C P
2, 3-Dec enoyl-A C P
3-OH-A c yl-A C P 3-Oxoac yl-A C P
3-Oxo-Dec anoyl-A C P
3-Oxo-Hexanoyl-A C P3-OH-Hexanoyl-A C P2, 3-Hexenoyl-A C P
B utanoyl-A C P C rotonoyl-A C P 3-OH-B utanoyl-A C P A c etoac etyl-A C P
Hexanoyl-A C P
3-OH-Dec anoyl-A C PDec anoyl-A C P
P almitoleoyl-A C P
γ-L inolenate A rac hidonate L eukotriene B 4
C OS C oA
C O-S -AC P
T hromboxane B 2
HOOC C H C O-S -AC P2
Malonyl-A C P
HOOC C H C O-S C oA2
Malonyl-C o-A
C H C O-S -AC P3
A c etyl-A C P
C H O-C O-R2
C H OH2
R ’-C O-OC H
F A T T Y A C ID
A C Y L -C oA
(C ytos ol)
C H O-C O-R2
C H O2
R ’-C O-OC H
P
C ardiolipin P hos phatidylglyc erol
A c etylc holine
G lyc erophos phoc holine 
L ys olec ithin
C holine
plas malogen
C DP -c holine C holine-P
Mevaldate
C H (C H ) C H=C HC H(OH)C HC H OH3 2 12 2
Dehydros phinganin S phinganin 4-S phingenin P s yc hos ine
A c yl-C oA
A c yl-C oA
C erebros ide
G alac tos eC H (C H ) C H=C HC H(OH)C HC H O-3 2 12 2
NHC OR
Is opentenyl-P P
(C 5)
Dimethylallyl-P P
(C 5)
G eranyl-geranyl-P P
(C 20)
F arnes yl-P P
(C 15)
S qualene
(C 30)
G eranyl-P P
(C 10)
Des mos terol Zymos terol L anos terol
C H C = C HC H O3 2 P P
C H3
C eramide
G anglios ides
NHC OR
C H O2 P P
O P P
C H2
C HOL E S T E R OL
C H C (OH)C H C H OH3 2 2
C H C OO2
C H C (OH)C H C HO3 2
C H C OO2
NADP +
Dehydroas c orbate
OH
H O
HOC H 2 C C C C C O
OHH OH
OH
H O
HOC H2 C C C O C O C O
H
NA D+
P i
A DPA DP
P hytoene
(C 40)
L yc opene (C 40)
ß-C A R OT E NE (C 40)
R hodops inMetarhodops in
R etinoate
trans -R etinal
11-c is -R etinoltrans -R etinol
(V itamin A )
R etinol es ters
Dark
L ight
Ubiquinone
(C oenzyme Q)
Menaquinone
P las toquinone
P hylloquinone
(V itamin K )
Ops in
C HO
C H OH2
C HO
C H OH2
C H3C H O3
C H O3 n
O
O
O
O
P hytol (C 20)
α-T oc opherol
(V itamin E )
Quinolinate
Quinolinate-
nuc leotide
Nic otinate-
nuc leotide
Des amino-NA D
5-Hydroxy-
tryptophan 
5-Hydroxytryptamine
(S E R OTONIN) 
N-A c etyl-5-O-methyl-s erotonin
(ME L A TONIN)
NH
C H C H NHC OC H2 2 3HO
NH
C H C H NHC OC H2 2 3C H O3
+NA D( P )
NIC OT INA T E
N-A c etyl-s erotonin
2.4.2.19
Dopamine Dopa
Dopaquinone
T HY R OXINEME L A NIN
OH
OH
C HOHC H NHC H2 3
OH
OH
C HOHC H NH2 2
4-OH-3-Methoxy-
phenylglyc ol
C HOHC H NH2 2
OH
OC H 3OC H 3
C HOHC H OH2
OH
OC H 3
4-OH-3-Methoxy-
D-mandelate
C yc lic A MP
A T P
Dephos pho-C oenzyme A
4-P -P antetheine
4-P -P antothenylc ys teine
4-P -P antothenate
P antoate
6.3.2.1
1.1.1.169
3.5.1.22
2.7.1.33
NH
NH 
O
O
O
O
C H OH2
OH
OC H 3
 C H(OH)C OO
H2
NH3
+
C H-C OO
CO
O
C OO
NR ibose- P
N
+
C OO
NH
C H C OO2
O
OH
C H O2 P
NHC OC H NH2 2
OH
F ormyl
glyc inamide-R P
Urea
F ormyl
glyc inamidine-R P
A llantoate A llantoin UR A T E
A DP
Xanthine Hypoxanthine
Inos ine
A denine
A denylo-
s uc c inate
5-A mino
imidazole-R P
5-A mino-4-imidazole
c arboxylate-R P
5-A mino-4-imidazole
(N-s uc c inylc arboxamide)-R P
5-A minoimidazole
c arboxamide-R P
F ormylamido-
imidazole-
c arboxamide-R P
 H NC ONH2 2
HN
H C2 C HO
NH
R P
NH
C
C
C
O
C
C O
OC
NH
N H
H
N
HN
H
C
C
O
C
C H
OC
NH
N
N
HN
C arbamoyl
ß-alanine
Dihydro-
urac il Urac il
d-A DP
d-A T P
G T P G DP
XA NT HOS INE -P
(XMP )
T T P
T DP
ß-Ureido
is obutyrate
Dihydro
thymine
T hymine d-UMP d-C MP d-C DP
C DP
C arbamoyl
as partate
Dihydro
orotate
Orotate Orotidine-P Uridine-P
(UMP )
UDP
3-A mino-
is obutyrate
C H
C
NH 2
C HOC
NH
NC H
C
O
C HOC
N H
HN
C H-C H3
C
O
OC
N H
HN
C H 2
C H2
C H2
C
O
OC
NH
HN
C
O
C HOC
N H
HN C C H3
Methylmalonyl
s emialdehyde 
OHC C HC OO
C H3
C H2
C
O
C H-C OOOC
N H
HN C H
C
O
C -C OOOC
N H
HN
H NC ONHC H C H C OO2 2 2
C
C
C
C H
R P
HC
NH
NH
 OOC -C H-C H C OO2
N
N
N
C HO
NH
R P
NH
OC
H C2
2.7.7.43
3.1.3.29
1.1.1.158
5.1.3.13
2.7.1.38
3.2.1.23
3.1.3.29
4.1.3.20
2.7.1.60
5.1.3.14
5.1.3.7
5.1.3.1
2.7.1.4
5.4.2.3
3.1
.1.1
7
1.1.1.49
1.1.1.
21
2.7.7.23
3.1.3.251.13.99.11.1.1.19
1.1.3.8
5.3.1.3
2.7.1.53
1.1.1.9
2.7.1.15
2.7.1.17
5.1.3.4
5.1.3.1
2.2.1.2
4.1.2.13
2.7.1.11
2.7.1.47
2.2.1.1
1.2.1.12
1.1.1.29
1.1.1.95
1.3.1.35
1.14.99.25
2.3.1.41
2.3.1.41
2.3.1.41
1.1.1.100
5.3.99.5
4.2.1.60
5.3.99.3
1.14.99.1
1.13.11.34
1.3.1.10
1.3.1.9
1.14.99.5
1.3.1.9
4.2.1.61
4.2.1.60
4.2.1
.60
4.2.1.59
4.2.1.58
1.3.1.9
1.3.1.9
6.2.1.3 3.1.2.20
1.1.1.100
5.3.
1.1
HOOC -C OOH
Oxalate
G lyc olate
HOC H C HO2
G lyc ol
aldehyde
E thanolamine-P
2.7.1.30
2.3.1.7
3.7
.1.
2
4.1.3.5
2.7.8.8
2.1.1.17
2.1.1.71
1.3.1.35 2.7.8.2
3.1.4.3
3.1.4.4
2.7.7.15
3.1.1.5 3.1.4.2
2.7.1.32
2.7.1.82
1.2.4.1
2.3.1.12
1.8.1.4
2.6.1.2
1.4.1.1
4.1
.1.1
2.3.1.50
1.1.1.102
3.1.4.12
2.7.8
.3
2.4.1.62
3.2.1.46
5.2.1.3
1.2.1.36
2.3.1.76
3.1.1.21
5.2.1.7
5.4.99.7
1.14.99.7
4.3.1.8
4.2.1.75
4.1.1.371.3.3.31.3.3.4
4.99.1.1
2.5.1.29
2.4.1.47
4.1.1.28 2.3.1.5 2.1.1.4
6.3.5.1
6.3.1.5
2.4.2
.11
2.7.7.18
2.6.1.5
1.2.1.32
1.13.11.5
2.1.1.28
2.1.2.2 6.3.3.1
3.5.2.5
1.4
.1.1
0
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
A C E T A T E
2.4.2.4
2.1.1.45
R P
C H
C
O
C HOC 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
L A C T A T E
A c etaldehyde
2.7.1.24
2.7.7.3
4.1.1.36
B ile A c ids
C H C H C OS C oA3 2
P ropanoyl-C oA
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
C DP -E thanolamine
1.1.1.35 4.2.1.17
+
HO S C H C H(NH )C OO2 2 3
3.5.2.7NHHN
C H
 OOC C HC H C H C OO2 2
C MP -N-A c etyl
neuraminate
C DP -diac yl
glyc erol
C HOL INE
E thanolamine
G lyoxylate
HIS T A MINE
2.3.1.46
Homos erine
T yramine
P lant P igmentsT annins
Maleyl
ac etoac etate
F umaryl
ac etoac etate
5.2.1.2
C H C OO2
OH
OH
OH
C H C H NH2 2 2
OH
OH
C H C H NH2 2 2
Hydroxyphenyl
pyruvate
α-T oc opherol
(V itamin E )
L IG NIN
d-G T P
OH
OH OH
O
HO
OH
P
OP P T
C H3HO
OHOH
O
NA DP H
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
A T P
C H C H NH2 2 2
NH
HO
5.4.99.5
1.14.16.12.6.1.51.13.11.27
Indole
4.1.99.1
1.13.11.11
OH
O
OH
NH C C C H C H O2 P
H HC OO
NH2
C OO
6.3.5.3 6.3.2.6 4.3.2.2
G uanine
DNA
6.3.4.44.3.2.2
C
C
O
C
C H
HC
NH
N
N
HN C
C
O
C
C H
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
3.5.2.23.5.1.6
3.5.1.6 3.5.2.2 3.5.4.1
Diphos pho-
mevalonate
Mevalonate
3-Oxopentanoyl-C oA
3-Oxoac yl-C oA3-OH-A c yl-C oA2, 3-E noyl-C oA
2, 3-Hexenoyl-C oA 3-OH-Hexanoyl-C oA
A c etoac etyl-C oA3-OH-B utanoyl-C oAC rotonoyl-C oA
P entanoyl-C oA 3-OH-P entanoyl-C oA
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 F atty ac ids
S uc c inylhomos erine
C O 2
2-OXO A C ID
G lutamyl-P
G lutamine
UR E A
P -C reatineC reatine C reatinine
G lyc ine
C IT R UL L INE
G lutamic 
s emialdehyde
2-A MINO A C ID
P yrroline-5-
c arboxylate
G lyoxylateP yruvate
4-Hydroxy-
2-oxoglutarate
4-Hydroxy-
glutamate
3-Hydroxy-
pyrroline-
5-c arboxylate
P utres c ine
H NC H C H C H C H NH2 2 2 2 2 2
S permidine
S permine
N -T rimethyllys ine66N -T rimethyl-
3-OH-lys ine
C arnitine
G lutaryl-C oA S ac c haropine2-A minoadipate
s emialdehyde
2-A minoadipate2-Oxoadipate
A rginino-
s uc c inate
G uanidoac etate
Methylmalonyl-C oA
4.1.2.12
A s partyl
S emialdehyde
2, 3-Dihydro-
dipic olinate
1.2.1.11
4.2.1.52 1.3.1.26 P iperideine-
2, 6-dic arboxylate
N-S uc c inyl-
2-amino-6-oxo-
pimelate
2.6.1.17N-S uc c inyl-2, 6
diaminopimelate
Diamino-
pimelate
3.5.1.18
3-Methyl-
glutac onyl-C oA
(C H ) C HC H C OS C oA3 2 2(C H ) C HC H C OS C oA3 2 2
3-Methyl-
c rotonyl-C oA
Is ovaleryl-C oA
OxopantoateHC HO
 OOC C H C = C HC OS C oA2
C H3
C H C OC HC OS C oA3
C H3
C H C H=C HC OS C oA3
C H3
C H C H(OH)C HC OS C oA3
C H 3
C (OH)C H(OH)C OO
C H C H3 2
C H3
C H = C C OS C oA2
C H3
HOC H C HC OS -C oA-2
C H3
C H C HC O-S C oA3
C H3
C (OH)C H(OH)C OO
C H3
C H3
C H C H C HC OS C oA3 2
C H 3
C H C = C HC OS C oA3
C H3
A T P
4-A minobutyrate
(G A B A )
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
Oxoleuc ine
C OOH
(C H ) C HC HC H(OH)C OO3 2
S -A denos ylmethyl
thiopropylamine
(Dec arboxylated S A M)
P R OL INE
C oenzyme A
C H C = C HC H3 2
C H 3
O
C H
C H
3
3
HO
C H3C H3
C H 3
C H C -C H H O3 2 2C P P
C H2
C H C = C HC H O2 2 P P
C H3
3-P -G lyc erol
P hos phatidyl
ethanolamine
C E P HA L IN
3.1.4.1
2
2.7.8.3
P roges terone
1.5.1.12
2.7.3.2
4.2.1.173.1.2.4
2.6.1.32
4.4.1.15
A c etyls erine 2.7.7.42.7.1.251.8.99.1
A denylyls ulphate
(A P S )
2.7.1.39
4.4.1.15
4.1.1.29
4.2.99.8
2.3.1.30
P -R ibos yl-P P
1.1.1.1
1.2.1.4
A s partyl-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
C HOL INE
2.1.1.13
1.3.1.2
NHC H C H S H2 2 NHC H C H C O2 2OC H C (C H ) C H(OH)C O2 3 2P
ADP - NHC H C H S H2 2 NHC H C H C O2 2OC H C (C H ) C H(OH)C O2 3 2
P -ADP - NHC H C H S H2 2 NHC H C H C O2 2OC H C (C H ) C H(OH)C O2 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
+
C H C O-OC H C H(NH )C OO2 2 3
2.5.1.6
2.1.1.10
2.1.1.20
1.1.1.3
1.1.1.3
4.2.1.18
4.1.2.5
4.3.1.5
4.2.1.2
0
2.1.2.1
2.
1.
1.
20
G lyoxylate
2.1
.1.6
1.4
.3.
4
1.14.18.1
1.14.16.2
Hexanoyl-C oA
B utanoyl-C oA
6.3.4.16
6.3.5.5
2.7.2.11
2.1.3.3
NO
1.14.13.39
3.5.3.63.5.3.1
4.3.2.1
4.1.1.17
2.7.7.41
2.6
.1.
4
1.1.1.100
1.1.1.8
2.3.1.51
2.3.1.15
2.7.8.5
S O -4
2
1.14.16.4
NH 2 OOC 
 OOC 
4.1.1.25
1.3.1.13
1.3.1.13
2.7.4.6
C Y T IDINE -
triphos phate
(C T P )
C ytos ine
2.4.2.9
4.1.1.11
2.6.1.18
4.3.1.3
4.2.1.49
3HS O
-
1.1.1.105
2.3.1.41
NA DP H
1.1.1.2
2
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
OP P U
C H OH2
C H OH2
HO OH
OH
HO
2.4.1.21
4.2.1.52
1.2.1.18
4.2.1.18
O
C H
C
C HOC
N
HN
DP
C H
C
O
C HOC
N
HN
R P P P
OC H 2
H
C C
H
OHOH
C H
NHN
C
H
CP
H
O
OC H2 C C
H
OH
H
OH
C
H
C C
C
NH2
C
C H
HC
N
R P (P P )
N
N
N
+
P 
NH2H
O
OC H 2 C C
H
OH
H
OH
C
H
C C
OC
C
C H
HC
N
R P
N
N
NHP
H
OC H 2 C C
H
OHOH
C O C H2 C
C ONH 2
C
C H
HC
N
R P 
N
N
NHP
+
OOC C H N(C H )2 3 3
B etaine
B etaine
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
C H 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-C oA
6.3.4.5
5.3.1.6
2.5.1.21
2.1.1.2
3.5.2.10
6.3.2.13
6.3.2.7-10
2.7.7.27
2.7.7.9
3.5.4.10
C
C
O
C
C H
OC
N R P
N
N
H
HN
C
C
O
C
C H
N
N
N
HN
R P
H N2 C
2.7.4.6
1.17.4.1
2.7.4.6
2.6.1.13
C arbamoyl-P
2.3.1.9
C arnitine
2.6.1.4 2
.6.1.44
C H C (OH)C H C OS C oA3 2
C H C OO2
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
C arnos ine
C H C H NH2 2 2C
NHN
C
HC
H
4.1.1.22
4.3.1.3
Ubiquinone
P las toquinone
D-R ibos e-5-P
NH
C H C H(NH )C OO2 3HO
+
O
OH
OH
HO
OP P U
C OO -
O
OH
OH
HO OP P U
C OO -
OH
H OH
HOC H 2 C C C O
H
C O C OO -
O
C HOH
C HOHAcNH
HO
OP C
OC O -
C H OH2
O
C HOH
C HOHAcNH
HO
OH
C OO
C H OH2
O
OHOH HOHO
C H O2 P
O
OH
AC NH
HO OH
C H O2 P
O
OOH HOHO P 
C H OH2
O
OHOH HOHO
C H OH2
O
OHHO OH
3
C H O2 P
O
OHHO O
NHC OC H 3
P 
C H OH2C H OH2C H OH2
O
OHHO OH
NH2
C H O2 P
O
OH
HO
OH
OP P U
C H OH2
O
O
HO
OH
OH
HO
P
C H OH2
C H OH2
O
O
HO
OH
OH
O
OHOH
OH
C H OH2
O
OHHO
OH
OH
C H2C H OP2
OH
H H HOH
C C C C
OH OHH
C OO -HOC H 2
H
OH OHOH
C C C C HO
HH
HOC H 2
H
OH OHH
C C C C HO
HOH
HOC H 2
OH
H OHH
C C C C HO
HOH
HOC H 2
H
OH HOH
C C C C HO
OHH
HOC H 2
OH
H HOH
C C C C HO
OHH
HOC H 2
OHH OHOH
C C C C HO
HH
HOC H 2
H
OH HOH
C C C C
OHH H
OH
C OO -P OC H2
OH
H OH
C C C O
H
P OC H2 C H OH2
H
OH H
C C C O
OH
HOC H 2 C H OH2
C H OH2P OC H 2
H
OH OH
C C C O
H
C H OH2P OC H2
OH
H H
C C C O
OH
C H OH2P OC H2
H
OH OH
C C C O
H
HOC H 2 C H OH2
OH
H OH
C C C O
H
HOC H 2
C H OH2
OH
H H
C C C O
OH
HOC H 2 C H OH2
H
OH OHH
C C C
HOH
HOC H 2 C H OH2
OH
H OHOH
C C C
HH
HOC H 2 C H OH2
H
OH HOH
C C C C
OHH H
OH
C H OH2HOC H 2
H
OH OH
C C C HO
H
P OC H 2
H
OH HOH
C C C C O
OHH
HOC H 2 C H O2 P
H
OH OHOH
C C C
HH
HOC H 2 C H OH2
H
OH OH
C C C
H
C O
H
HO
P OC H2 C H OH2
P
H
OH OH
C C C
H
C O
H
HO
C H O2 POC H 2
H
OH OH
C C
H
C C HO
OH
H
P OC H 2P OC H 2
O
OH
NH2
OH
C H O2 P
 C HOHC HOP OC H 2
HOC H2C OC H2OP
O
OH
O OP P
OH
C H O2 P
C HOHC OO PP OC H 2
 C HOHP OC H2 C OO
C OO
OH
OHO
OH
C OO
C H (C H ) C H(OH)C H C OS -C oA3 2 14 2C H (C H ) C H(OH)C H C OS3 2 14 2
C H (C H ) C OC H C OS -C oA3 2 14 2
C H (C H ) C OC H C OS -C oA3 2 14 2
C H (C H ) C OS -C oA3 2 n+2
C H (C H ) C H=C HC OS -C oA3 2 14
C H (C H )3 2 nC H=C HC OS -C oA
C H (C H )3 2 5 2C H=C HC H C OS AC P
C H (C H )3 2 6C H=C HC OS AC P
C H (C H )3 2 6C OC H C OS AC P2C H (C H )3 2 6 2 2C H C H C OS AC P
C H (C H )3 2 2 2 2C H C H C OS AC P
C H C H C H C OS AC P3 2 2
C H (C H )3 2 6C H(OH)C H C OS AC P2
C H C H=C HC O.S -AC P3
C H (C H )3 2 2 2C OC H C OS AC P
C H3C OC H C OS AC P2
C H (C H )3 2 n 2C OC H C OS AC PC H (C H )3 2 n 2C H(OH)C H C OS AC P
C H (C H )3 2 2 2C H(OH)C H C OS AC P
A C Y L -C oA
(Mitoc hondria)
C H (C H ) C H C H C OS C oA3 2 2 2n
C H (C H ) C H=C HC OS C oA3 2 n C H (C H C H(OH)C H C OS C oA3 2n
C H (C H ) C H C H C OS C oA3 2 2 2 2 C H (C H ) C H=C HC OS C oA3 2 2
C H (C H ) C OC H C OS C oA3 2 2n
C H C OC H C OS C oA3 2
C H (C H ) C H(OH)C H C OS C oA3 2 2 2
C H C H(OH)C H C OS C oA3 2C H C H=C HC OS C oA3C H C H C H C OS C oA3 2 2
C H C H C H C H C OS C oA3 2 2 2
P entenoyl-C oA
C H C H C H=C HC OS C oA3 2 C H C H C H(OH)C H C OS C oA3 2 2
C H (C H ) C OC H C OS C oA3 2 2 2
C H C H C OC H C OS C oA3 2 2
OH OH
HO OH
O
O-
C H O-P O2
 C H C HOHC H OH2 2
O
C H2
C H2
R '-C O-OC H
O-C O-R
O-P O
O-
HOC H C H2 2NH 3
+P OC H C H2 2NH3
+
C P P - OC H C H2 2 NH3
+
O
-
C H O-C O-R2
C H O P2 OC H C H2 2NH 3
+
C H C OC H C H N(C H )3 2 2 3 3
HOC H C H N(C H )2 2 3 3
+
C H C H 2 C OO(NH )3
+
OH
OH
C H C H 2 C OO- (NH )3
+
C O
NH2
C H C H(NH )C OO2 3
+
NH
OC
C O
NH
OC
N
H
C
H
H N2
HC
C H
N
N
C
R P
H N2
C H
C
C HOC
N
N
DP
NH2
R P P P
C H
C
C HOC
N
N
NH 2
C
C
C
C H
R P (P )
HC
N
N
N
N
NH2
H NC OO2 P
(C H ) NH2 3 2H N(C H ) NH2 2 3 (C H ) NH2 4
(C H ) NH2 3 2H N(C H ) NH2 2 4
C H -S C H C H C HNH3 2 2 2
A denos yl
+
+
C H3
C H3
C HC H(NH )C OO3
++
C
NHN
C
HC
H
C H C H(NH )C H OH2 3 2
+
C
NHN
C
HC
H
C H C H(NH )C H OP2 3 2
C
NHN
C
H
HC C H C OC H OP2 2
+
HS C H C H C H(NH )C OO2 2 3
+
+
S C H C H C H(NH )C OO2 2 3
C H C H(NH )C OO2 3
R P
C
O
C -C OOOC
N
HN C H
2.4.1.23
C H (C H ) C H=C HC H(OH)C HC H OH3 2 12 2
NH 3
+
C H (C H ) C H(OH)C HC H OH3 2 14 2
NH 3
+
C H (C H ) C OC HC H OH3 2 14 2
NH 3
+
G alac tos eC H (C H ) C H=C HC H(OH)C HC H O-3 2 12 2
NH 3
+
4.1.1.70
H NC ONH2 2
OHC C H N(C H )2 3 3
+
C -C H3
C
O
C HOC
N DP
HN
DP
C P P -O C H C H N(C H )2 2 3 3
+
OC H C H N(C H )2 2 3 3
+
1.2.1.41
UDP -N-A c -Muramate
O
O
C H C H3
C OO-
NHAC
HO OP P U
C H OH2
4.1.3.20
O
OH
C H3
HO HO OP P G
2.7.7.24
2.4.1.22
2.7.7.12
5.1.3.2
5.3.1.4
S edoheptulos e-P P
3.1.1.28
4.2.1.24
N
C H2
C H2
N
N
N
C H3
C H3
C H
C H
C OO
C H
C H
C H2
H C3
H C3H C3
HC
C
C
H
H
F e
C H2
C H2
C OO - -
C H3
C H3
C H2
C H2
C H2
H C3
H C3
N
H
N
H
N
H
N
H
C H
C H
H C2
C
C
H2
H2
-
C H2
C H2
C OO
C H2
C H2
C OO -
H C2
H C2
C H 2
C H 2
 OOC
C OO
H N2
N
H
-
-
C H2
H C2
H C2
H C2
H2
H2
C H2
C H2 C H2
C H2
C H2
C H2
N
H
N
H
N
H
N
H
C OO
C OO
C OO
C OO
C
C
-
-
C H2
C H2
C OO
C H2
C H2
C OO- -
-
-
 OOC-
 OOC
-
C H3
C H3
H C3
H C3
H C2
H2
H2
N
H
N
H
N
H
N
H
C H2
C H2
C H2
C H2
C H2
C
C
C OO-
C H2
C H2
C OO
C H2
C H2
C OO- -
C OO-
C OO-
C H C (OH)C H C H O3 2 2 P P
C H C OO2
OHC C OO
HOC H C OO2
NH2
H NC NHC H C OO2 2
+ NH2
H NC N(C H )C H C OO2 3 2
+ NH2
HNC N(C H )C H C OO3 2P -
+ HN C
NH C O
N C H 2
C H3
 OOC C HC H C OO2
H NC NHC H C H C H C H2 2 2 2
N
(NH )3
+
C OO
C HC OOHC
C H2HOC H
N
 OOC C H(OH)C H C H(NH )C OO2 3
+
C HC OO
C H2HOC H
H C2
N
H
NH
C HC OO
C H2C H2
C H2
 OOC C H(OH)C H C OC OO2
N
C HC OO
C H2C H2
C H
C H C OC OO3 OHC C OO
+
H NC ONHC H C H C H C H2 2 2 2 (NH )3 C OO
H NOC C H C H C H2 2 2 C OO(NH )3
+
R -C O-C OO
+
C OOR -C H(NH )3
+
C OOH NOC C H C H2 2 (NH 3
+
 OOC -C H-C OS C oA
C H3
P OOC C H C H2 C OO(NH )3
+
 OOC C H C H C HO2 2
OHC C H C H2 C OO(NH )3
+
(C H ) NC H C H(OH)C H C OO3 3 2 2
+
OHC C H C H C H2 2
+
C OO(NH )3
P OOC C H C H C H2 2
+
C OO(NH )3
OHC C H C H C H C H2 2 2 C OO(NH )3
+
NH C HC H C H C OO2 2
C OO
 C H C H C H C H C H2 2 2 2 C OO(NH )3
+
H N(C H )2 42 C H(NH )C OO3C H(NH 3
++
(C H ) N(C H )3 3 2 3 C H C H(NH )C OO2 3
+ +
C H 2
C
H
 OOC C
N
HC
C H-C OO
C H2
C
H2
C H-C OO OOC C
N
H C2
OOC C OC H C H C H C H-C OO2 2 2C H C H2 2 2
 OOC C H C H C ONH2 2 OOC C HC H C H C H C H-C OO2 2 2
 OOC C H C H C ONH2 2C H2 2
NH3
+
OOC C H-C H C H C H C HC OO2 2 2
NH 3
+
NH3
+
(C H ) C HC (OH)C H3 2 2
C OOH
C OO (C H ) C HC H C OC OO3 2 2
+
(C H ) C HC H3 2 2 C H(NH )C OO3
HOC H C HC OO2
C H3
C HC OC OO
C H3
C H3C H C OC (OH)C H3 3
C OO
+
P OC H C H C H(NH )C OO2 2 3
+
HOC H C H C H(NH )C OO2 2 3
+
C H C H C H(NH )C OO2 2 3 OOC C H C H2C OO 2
+
C H S H2
 OOC C H(NH )C H C H C ONHC HC ONHC H C OO3 2 2 2
HOC H C (C H ) C OC OO2 3 2
HOC H C (C H ) C H(OH)C OO2 3 2
 NHC H C H C OO2 2HOC H C (C H ) C H(OH)C O3 2)2 3 2
 NHC H C H C OO2 2OC H C (C H ) C H(OH)C O2 3 2P
C H C H3 2
C H 3
C H
+
C H(NH )C OO3
C H C OC (OH)C H C H3 2 3
C OO C HC OC OO
C H C H3 2
C H3
NHC HC H S H2
C OO
 NHC H C H C O2 2OC H C (C H ) C H(OH)C O2 3 2P
+
C H S H2
 OOC C H(NH )C H C H C ONHC HC OO3 2 2
+
Adenosyl
S C H C H C H(NH )C OO2 2 3
+
S C H C H C H(NH )C OO2 2 3
+
HO S C H C H(NH )C OO3 2 3
+
+
S -C H C H(NH )C OO2 3
S -C H C H(NH )C OO2 3
+
HS C H C H(NH )C OO2 3
1.1.1.23
H
C
NHN
C
HC C H C HC OO2
NHC OC H C H NH2 2 2
+
H
C
NHN
C
HC C H C H(NH )C OO2 3
C HC H C H C OO2 2
NHN
C H
O C C C H C HC OO
NHN
C H
C H
C H C OO3
N
H
OOC
C H-C OOOC
NH2 C H2
H NC H C H C OO2 2 2H NC H2 2
C H3
C HC OO H NC ONHC H C HC OO2 2
C H3
C
C
O
C H
R PHC N
N
N
HN
C
CC
O
C H
HC O
N
N
N R P
C
C H
N
N
H N2
H
C
C
C
O
C H
N
N
C
C
C H
N
N
R P
H N2
H N2
C
O
O
O P~ ~P O
O
O O
P O
O
C H2
N
N
N
N
O
OHOH
NH2
HC
C HN
N
N
N
 O
O
P O O
O
C H2
OH
NH2
HC
C H
C OO
C O
NH
OC
N
H
C
H
H N2
NH2
 OOC -C H-C H C OO2
HNC O C
C H
N
N
C
R PR P
H N2
 OOC
C
C H
N
R P
N
C
H N2
C H=C HC OO
OH
C H=C HC OO
C H C OC OO2
C H2
P 
C OO
OH
O
O
O
C OO
O
C H C OO2
O
C H C OO2-OOC
OC H 2 C H2
OHH
C
P
HOC H HC OH
OC
C OO
C OOHO
OH
OHO
NH2C OO
OC H
NH
C H C OC OO2
NH
C HO
C O
NH2
OH
C H C H(NH )C OO2 3
+ 
N
C OO
C OO
N
+
C OO
C OO
R P
O
OH
OH
HO OP P U
C OO
O
OH
NHC OC H 3
HO
OP P U
C OO
C H OH2
O
O
CC H
2 NHAC
HO OP P U
C OO
C H OH2
O
OHHO OH
OH
C OO
 OOC C H N(C H )2 3 2
Dimethylglyc ine
1.1.99.1
1.2.1.8
C OO
HO HO
C OO
O
HO OH
C OO
C H(O ) PP OC H2 C OO
 C H(OH)HOC H2 C OOC OO
 C H(O )PHOC H2 C OO
C H =C (O )2 P C OO
C ONH 2
R ibose -O - P - O - P - O- Adenosine(P )
+
N
O
O
O
O
+
C OO
N
R ibose - O - P - O - P - O -Adenosine
O
O
O
O
II
II
OH
O
C H C H 2 C OO(NH )3
+
E pinephrine
(A drenaline)
Norepinephrine
(Noradrenaline)
Normetepinephrine
(Normetadrenaline)
HOC H C H N (C H )2 2 3 3
+
Adenosyl
+
+
S C H C H C H(NH )C OO2 2 3
C H 3
(C H ) N(C H )3 3 2 3 C H C H(NH )C OO2 3
+ +
OH
 OOC C H C H C H C OS C oA2 2 2
 OOC C H C H C H NH2 2 2 2
 OOC C H C H C H C OC OO2 2 2 OOC C H C H C H C H2 2 2 C OOC OO(NH )3
++
HO
H
HO
H
H
HO
H
HO
H
P ros taglandin P G E2
OH
HOC H 2 C C C O C C OO
OHH
OHH H
-
C OO
OR '-C O-OC H
C H O-C O-R2
C H O P OC MP2
O
C H C H N(C H )2 2 3
+
OHOC H
C H OP O2
C H OH2
O-
C H OP O2
O
C H OC H=C HR2
C H C H N(C H )2 2 3 3
+
O-
C H OP O2
OR '-C O-OC H
C H O-C O-R2
3.1.1.32
C H C H N(C H )2 2 3 3
+
O-
OHOC H
C H OP O2
C H O-C O-R2
C H C H N(C H )2 2 3 3
+
O-
C H C H(NH )C OO2 3
+
+
C
NHN
C
HC
H
C H C H(NH )C HO2 3
HS
11-c is -R etinal
P i
A DP
NADP +
G DP -
Mannuronate
Mannos e-6-P
Dehydro-
s hikimate
S hikimate
R NA
d-G DP
d-C T P
G UA NOS INE -P
(G MP )
ß-A lanine
P -R ibos yl-A MP P -R ibulos ylformimino
5-aminoimidazole-
c arboxamide-R P
Imidazole
ac etol-P
HS HS O -
P A NTOT HE NA T E
3-Is opropyl-
malate
S uc c inic
s emialdehyde
2.4.1.17
Diac yl
glyc erol
2.3.1.6
1.14.12.1
1.4.4.2
C H C HO3
3.5.4.19
4.2.1.19
3.3.1.1
4.1.1.12
4.1.2.5
C OO-2OHC C H
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
A DP
P -G luc ono
lac tone
1.1.1.44
O
O
OHHO
OH
C H O2 P
P HE NY L A L A NINET Y R OS INE
T R Y P TOP HA N
INOS INE -P
(IMP )
T HY MIDINE -P
HIS T IDINE
UR IDINE -
triphos phate
(UT P )
C Y S T INE C Y S T E INE
IS OL E UC INE
L E UC INE
LY S INE
OR NIT HINE
A R G ININE
HY DR OXY
P R OL INE
P HOS P HA T IDY L
S E R INE P hos phatidyl
inos itol 
L E C IT HIN
S P HING OMY E L IN
S T E R OIDS
P regnenolone
2.7.6.1
2.4.2.14
6.3.4.7
5.3.1.9
3.1.3.11
1.2.1.13
2.7.2.3
H
OH OH
C C C
H
C O
OH
C
H
H
OH
P OC H2 C H O2 P
5.4.2.1
A DP
4.2.1.11
E ndoplas mic R etic ulum
1.1.1.100
3.1.1.3
P hos phatidate
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
P O
O
C H (C H ) C H=C HC H(OH)C HC H O3 2 12 2
NHAcyl
C H C H N(C H )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
ME T HIONINE
4.1.3.27
4.2.1.51
1.14.17.1
1.14.18.1
1.14.13.11
G lyc inamide-
ribos yl-P
4.2.1.22
3-Oxohexanoyl-C oA
T HR E ONINE
1.2.1.25
1.2.1.25
1.2.1.25
1.5.1.7 - 10
G L UT A MA T E
2.3.1.38
A T P
NA DH
S UC R OS E
A DE NOS INE -P
(A MP )
T riac ylglyc erol
F A T
R NA
C H 3
C H2
 OC -C OOOH
C OO
C H C H 2 C OO(NH )3
+
G LY C OP R OT E INS
G A NG L IOS IDE S
MUC INS
4.1.2.-
2.6.1.-
G L UC OS E
O-A c yl-c arnitine
O-A c yl-c arnitine
OH
O-
-
R -C O-OC H
R '-C O-OC H
R '-C O-OC H
O HC O-C O-R
 C H C H(OH)C H O-P -OC H2 2 2
C H O-C O-R ’2
OR '-C O-OC H
O -
C H O-C O-R2
C H O-P O2
O-
2.7.8.11
H NC H C H C H C H2 2 2 2 C OO(NH )3
+
2.3.1.20 3.1.3.4 2.7.1.107
NH2
+
+
H NC NHC H C H C H C H2 2 2 2 C OO(NH )3
H
OH HOH
C C C C O
OHH
HOC H 2
C H OH2
R -C H2C OO
C H O-C O-R2
C H O-C O-R "2
R ’-C O-OC H
OH
O
 C H C HNH2 3
+
OR '-C O-OC H
O-
C H O-C O-R2
C H O P O2
C OO
 OOC C H C H C H2 2 C OO(NH )3
+
C H C H(OH)C H(NH )C OO3 3
O
OHHO
OH
OH
C H OH2C H OH2
NH
C H O-C O-R2
1.3.1.13
4.1.1.28
Malonic
s emi-
aldehyde
2.7.2.4
2.1.3.3
3.5.1.2
6.3.1.2
6.3
.5.
5
C arbohydrates
B iosynthes is
Degradation
A mino A c ids
B iosynthes is
Degradation
L ipids
B iosynthes is
Degradation
P urines &
P yrimidines
B iosynthes is
Degradation
B iosynthes is Degradation
V itamins C o-enzymes & Hormones
P entos e P hos phate P athway
P hotos ynthes is Dark R eac tions
C OMP A R T ME NT A T ION
T he "B ackbone" of metabolism involves
G LY C OLY S IS in the C Y T OP LAS M,
the T C A C Y C LE (mainly) in the Mitochondrial matrix
and AT P F OR MAT ION spanning the
MIT OC HONDR IAL INNE R ME MB R ANE
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
E lectron F low P roton F low
S mall Numbers ( eg. 2.4.6.7) refer to the IUB MB E nzyme
C ommiss ion (E C ) R eference Numbers of E nzymes
L E G E ND
Human Metabolism is identified as far poss ible by black arrows
B iosynthes is Degradation
HE MOG L OB IN C HL OR OP HY L L
A T P
T
R
A
N
S
L
O
C
A
T E D P R OTONS
2.7.1.1
A T P
2.7.1.2
sigma-aldrich.com/pathw ays
A rgentina
SIGMA-ALDRICH DE 
ARGENTINA, S.A.
Tel: 54 11 4556 1472
Fax: 54 11 4552 1698
A ustralia
SIGMA-ALDRICH PTY., LIMITED
Free Tel: 1800 800 097 
Free Fax: 1800 800 096
Tel: 612 9841 0555
Fax: 612 9841 0500
A ustria
SIGMA-ALDRICH HANDELS GmbH
Tel: 43 1 605 81 10
Fax: 43 1 605 81 20
Belgium
SIGMA-ALDRICH NV/SA.
Free Tel: 0800-14747
Free Fax: 0800-14745
Tel: 03 899 13 01
Fax: 03 899 13 11
Brazil
SIGMA-ALDRICH BRASIL LTDA.
Tel: 55 11 3732-3100
Fax: 55 11 3733-5151
Canada
SIGMA-ALDRICH CANADA LTD.
Free Tel: 800-565-1400
Free Fax: 800-265-3858
Tel: 905-829-9500
Fax: 905-829-9292
China
SIGMA-ALDRICH CHINA INC.
Tel: 86-21-6386 2766
Fax: 86-21-6386 3966
Czech Republic
SIGMA-ALDRICH s.r.o.
Tel: 246 003 200
Fax: 246 003 291
Denmark
SIGMA-ALDRICH 
DENMARK A/S
Tel: 43 56 5910
Fax: 43 56 59 05
Finland
SIGMA-ALDRICH FINLAND
Tel: 358-9-350-92 50
Fax: 358-9-350-92 555
France
SIGMA-ALDRICH CHIMIE S.à.r.l.
Tel appel gratuit: 0800 211 408
Fax appel gratuit: 0800 031 052
Germany
SIGMA-ALDRICH CHEMIE GmbH
Free Tel: 0800-51 55 000
Free Fax: 0800-649 00 00
Greece
SIGMA-ALDRICH (O.M.) LTD
Tel: 30 210 9948010
Fax: 30 210 9943831
Hungary
SIGMA-ALDRICH Kft
Tel: 06-1-235-9054
Fax: 06-1-269-6470
Ingyenes zöld telefon: 06-80-355-355
Ingyenes zöld fax: 06-80-344-344
India
SIGMA-ALDRICH CHEMICALS 
PRIVATE LIMITED
Telephone
Bangalore: 91-80-5112-7272
Hyderabad:
91-40-5531 5548 / 2784 2378
Mumbai:
91-22-2579 7588 / 2570 2364
New Delhi:
91-11-2616 5477 / 2619 5360
Fax
Bangalore: 91-80-5112-7473
Hyderabad: 91-40-5531 5466
Mumbai: 91-22-2579 7589
New Delhi: 91-11-2616 5611
Ireland
SIGMA-ALDRICH IRELAND LTD.
Free Tel: 1800 200 888
Free Fax: 1800 600 222
Israel
SIGMA-ALDRICH ISRAEL LTD.
Tel: 08-948-4100
Fax: 08-948-4200
Italy
SIGMA-ALDRICH S.r.l.
Telefono: 02 33417310
Fax: 02 38010737
Numero Verde: 800-827018
Japan
SIGMA-ALDRICH JAPAN K.K.
Tokyo Tel: 03 5821 3111
Tokyo Fax: 03 5821 3170
K orea
SIGMA-ALDRICH KOREA
Tel: 031-329-9000
Fax: 031-329-9090
M alaysia
SIGMA-ALDRICH (M) SDN. BHD
Tel: 603-56353321
Fax: 603-56354116
M exico
SIGMA-ALDRICH QUÍMICA,
S.A. de C.V.
Free Tel: 01-800-007-5300
Free Fax: 01-800-712-9920
The Netherlands
SIGMA-ALDRICH CHEMIE BV
Tel Gratis: 0800-0229088
Fax Gratis: 0800-0229089
Tel: 078-6205411
Fax: 078-6205421
New Zealand
SIGMA-ALDRICH PTY., LIMITED
Free Tel: 0800 936 666
Free Fax: 0800 937 777
Norw ay
SIGMA-ALDRICH NORWAY AS
Tel: 23 17 60 60
Fax: 23 17 60 50
Poland
SIGMA-ALDRICH Sp. z o.o.
Tel: (+61) 829 01 00
Fax: (+61) 829 01 20
Portugal
SIGMA-ALDRICH QUÍMICA, S.A.
Free Tel: 800 20 21 80
Free Fax: 800 20 21 78
Russia
SIGMA-ALDRICH RUSSIA
TechCare Systems, Inc.
(SAF-LAB)
Tel: 095-975-1917/3321
Fax: 095-975-4792
Singapore
SIGMA-ALDRICH PTE. LTD.
Tel: 65-6271 1089
Fax: 65-6271 1571
South A frica
SIGMA-ALDRICH 
SOUTH AFRICA (PTY) LTD.
Tel: 27 11 979 1188
Fax: 27 11 979 1119
Spain
SIGMA-ALDRICH QUÍMICA S.A.
Free Tel: 900101376
Free Fax: 900102028
Sw eden
SIGMA-ALDRICH SWEDEN AB
Tel: 020-350510
Fax: 020-352522
Outside Sweden Tel: +46 8 7424200
Outside Sweden Fax: +46 8 7424243
Sw itzerland
FLUKA CHEMIE GmbH
Swiss Free Call: 0800 80 00 80
Tel: +41 81 755 2828
Fax: +41 81 755 2815
United K ingdom
SIGMA-ALDRICH COMPANY LTD.
Free Tel: 0800 717181
Free Fax: 0800 378785
Tel: 01747 833000
Fax: 01747 833313
United States
SIGMA-ALDRICH
P.O. Box 14508
St. Louis, Missouri 63178
Toll-free: 800-325-3010
Call Collect: 314-771-5750
Toll-Free Fax: 800-325-5052
Tel: 314-771-5765
Fax: 314-771-5757
Internet:
sigma-aldrich.com
© 2003 International Union of Biochemistry and M olecular Biology 
www.iubmb.org
22nd Edition Designed by Donald E. Nicholson, D.Sc., The University of Leeds, England – and Sigma-A ldrich
Product No. M 3907
XXX