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

G LY C OP R OT E INS G A NG L IOS IDE S MUC INS

AcNH C HOH C HOH

HY A L UR ONIC A C ID P E P T IDOG LY C A N C H
6.3.2.7-10 6.3.2.13 HO O
C H 3C H C OO2 OH

DE R MA T A N

C HIT IN
OP P U

C HONDR OIT IN
O C OO -

B L OOD G R OUP A L G INA T E S O-A NT IG E NS S TAR CH S UB S T A NC E S P E C T IN INUL IN C E L L UL OS E

2.4.1.68 2.4.1.69 1.1.1.132
O C H3 HO OH HO OP P G HO C H 3 O OP P T OH OH C H3

G LY C OG E N
HO C H 2 OH O O OH OH OH OH OH C H 2 OH O NH

C ONH 2 C H 2 C OO OH NH

C OO O O

R ibos e
+

-O - P - O - P - OO O

Adenos ine(P )

C OO

R ibos e

-O-P -O-P -O
O O

-Adenos ine
2.7.7.18

+ N

NIC OT INA T E
2. 4. 2. 11
N

C OO

C OO
+ C OO N RP

O C OO OP C

Indoleac etate
(A uxin)
1.2.3.7
C H 2 C HO

Indoxyl
HO NH

NA D( P )
+ C H 2 C H(NH 3)C OO HO NH NH

6.3.5.1 6.3.1.5
C H 2 C H 2 NH 2

R ibos e- P

Des amino-NA D
HO

Nic otinatenuc leotide

C H 3O NH

2.4.2.19
C H 2 C H 2 NHC OC H 3

Quinolinatenuc leotide
N

C H 2 OH
HO

2.4.99.7

2.4.2.19

NHAC

2.4.1.17

HO

OH

OP P U OH

2.4.1.29 2.4.1.21 2.4.1.1 etc. 2.4.1.11 HO 2.4.1.21

L A C TOS E
C H 2OH O OH OH OH

C H 2 C H 2 NHC OC H 3

C OO C OO

UDP -N-A c -Muramate

HO C H 2 OH O C OO OH OP P U NHC OC H 3

UDP Iduronate
5.1.3.12
C OO HO OH O

C MP -N-A c etyl neuraminate

AcNH O C HOH C HOH C H 2 OH C OO OH 2.7.7.43

G DP -F uc os e
4.2.1.47
C H 2 OH O

G DP Mannuronate

T DP -R hamnos e
O OP P T OH

3.2.1.23 2.7.1.38

5.1.3.13 O 2.4.1.33
C H 2 OH O HO OH HO OH

Indoleac etaldehyde
4.1.1.43
C H 2 C OC OO

NH

Indole
1.14.16.4

5-Hydroxytryptophan
+ C O C H 2 C H(NH 3 )C OO C HO

4.1.1.28

5-Hydroxytryptamine
(S E R OTONIN)

2.3.1.5

N-A c etyl-s erotonin

C OO OH NH 2

NH

2.1.1.4

N-A c etyl-5-O-methyl-s erotonin

(ME L A TONIN)
C OO OC H C OO NH 2

Quinolinate

OH

2.4.1.16 1.1.1.158
C H 2 OH O

HO OH HO OP P G

3.1.3.29
HO

G DP -Mannos e
OP P U OH C H 2 OH O

T DP -4-Oxo6-deoxygluc os e
4.2.1.46

A DP G luc os e

C H 2OH O OH HO OH HO

G A L A C TOS E
2.7.1.6
OP P U HO C H 2 OH O OH OP OH

+ C O C H 2 C H(NH 3 )C OO NH 2 OH

+ C O C H 2 C H(NH 3 )C OO NH 2

Indolepyruvate
2.4.1.22

NH

4.1.99.1

F ormylkynurenine
1.13.11.11
+ C H 2 C H(NH 3 )C OO NH

NH

3.5.1.9

N-A c -Neuraminate
(S ialate)
C H 2O P O

HO O C H2 C C OO

OP P U NHAC

UDP -N-A c G alac tos amine

C OO O

K ynurenine 1.14.13.9 3-Hydroxy kynurenine

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

3.7.1.3

UDP G alac turonate

OP P U

2.7.7.13

MA NNOS E
2.7.1.7
C H 2O P O

G DP -G luc os e
1. 1. 1. 22
2.7.7.27 2.7.7.34

UDP -G luc os e G alac tos e-P

2.7.7.9
C H 2 OH O HO OH HO HO 5.1.3.2 2.7.7.10

C H 2 C H 2 NH 2

UDP -N-A c G luc os amine pyruvate N-A c -Mannos amine-6-P

3.1.3.29 AC NH 4.1.3.20 HO OH OH
C H 2 OH O C H 2 OH O

HO OH HO O P

5.1.3.7
HO OH OH

Mannos e-1-P
5.4.2.8

5.1.3.6

T DP -G luc os e
2.7.7.24

C H 2 OH O OH OP P U OH

T ryptamine
C OO OC P OC H 2 C H 2 HOC H HC OH C

NH

4.1.1.28

4.2.1.20

T R Y P TOP HA N
HO C OO C OO OH OH OH OH

Indole-3-glyc erol-P
C OO HO OH

C OO HOC -C H(OH)C H(OH)C H 2 OP CH N

4.1.1.45 3-Hydroxy 1.13.11.6 2-A mino-3-c arboxy 2-A minomuc onateanthranilate muc onate s emialdehyde 6-s emialdehyde C OO H H C atec hol
NH C C C H C H 2O P C OO NH 2

OC H NH 2 C OO

A R O M A T I C A M I N O A C I D S

1. 4. 1. 19

1.2.1.32 1.14.12.1
OOC OOC C H 2 C OC OO NH 2

OH OH

UDP -G luc uronate

C H 2 OH O C H 2O P O OP NHC OC H 3 5.4.2.3 HO OH OH

2.7.7.12

1-(o-C arboxy phenylamino) 1-deoxyribulos e-5-P

C OO

4.1.1.48

N-(5-P -R ibos yl) anthranilate

C OO C H2

2.4.2.18

A nthranilate
OOC

C OO

2-A mino muc onate

4.1.3.20
OP P U

HO OH HO OH

C H2

4.1.3.27 5.4.99.5
OH

H E X O S E S

AC NH HO OH OH

2.7.1.60
HO OH NHAC HO OH

Mannos e-6-P
2.4.1.9

2.4.1.13

C H 2O P O HO OH OH NH 2

OP

UDP -G alac tos e

C H 2 OH O

N-A c -Mannos amine

5.1.3.14

UDP -N-A c -G luc os amine

C OO O

2.7.7.23
OH

N-A c -G luc os amine-1-P

OH OH OH OH OP HO OH
OH

N-A c -G luc os amine-6-P

H H C OH C CO C H 2 OH C

NHC OC H 3

G luc os e-1-P

3-Deoxy-D-arabinoheptulos onate-7-P
O -OOC O C H 2 C OO

OH

4.6.1.3
O

Dehydroquinate

4.2.1.10

Dehydros hikimate
C H 2 C OO

1.1.1.25

S hikimate

OH

P O

2.7.1.71

OH

C H 2 C OC OO

S hikimate-3-P PEP

OH

OH

P O

2.5.1.19

S hikimate-5 4.6.1.4 enolpyruvate 3-P

+

OH

O-C -C OO

C horis mate
+

OH

OC -C OO

P rephenate
C H 2 C OC OO

C H 2 C H (NH 3 ) C OO

C H 2 C H(NH 3 ) C OO

2. 3. 1.
5.3.1.8

OH H HOC H 2 C H C

OH OH C C H

HOC H 2

G luc os amine-6-P
3.2.1.26 3.2.1.48

HO OH
OH

OH

C OO -

OH OH H

HO OH

OH OH

HO OH

OH H OH H

G ulonate
3.1.1.18 HOC H 2
C H C C H O

1.1.1.19
OH OH C H CO

G luc uronate
OH H HOC H 2 C H C OH C H O

1.13.99.1
CO CO

Inos itol
HOC H 2 C H

3.1.3.25
OH H C

OH

F ruc tos e
1.1.1.14
H H C OH H C C C H 2 OH OH

S UC R OS E
5.5.1.4

G L UC OS E
5.4.2.2 3.1.3.9 2.7.1.2 2.7.1.1

F umaryl 5.2.1.2 Maleyl 1.13.11.5 Homogentis ate ac etoac etate ac etoac etate
C HOHC H 2 NHC H 3 OH OH C HOHC H 2 NH 2 OH

C OO

O C H 2 C OO

4.2.1.51 1.3.1.13

OH

1.13.11.27

Hydroxyphenyl pyruvate 1.3.1.13

OH

OH

2.6.1.5

OH

T Y R OS INE

1.14.16.1

P HE NY L A L A NINE
1.3.1.13

2.6.1.5 4. 3. 1. 5

P henylpyruvate

Inos itol-P
C CO
HOC H 2 C

C H 2 C H 2 NH 2

+ C H 2 C H (NH 3 ) C OOOH

4 .1

.1 .2

OH OH C O
C H 2O P O

1. 1. 1.

21
2.6.1.16

ATP

E pinephrine
(A drenaline)

2.1.1.28

OH

Norepinephrine
(Noradrenaline)
.1 .6 2 .1

1.14.17.1

Dopamine -T oc opherol
(V itamin E )

OH

4.1.1.28 1.14.18.1
O

Dopa
H2 C C H-C OO + NH 3

OH

1.14.16.2

Ubiquinone
O O

C H 2 C H 2 NH 2

C H=C HC OO

+ C H 2 C H (NH 3 ) C OO

T yramine

OH

C innamate Menaquinone
1.14.13.11
C H=C HC OO

G ulonolac tone 1.1.3.8 2-Oxogulonolac tone

1.1.1.45
OH H C OH OH OH H HOC H 2 C H C OH CO HOC H 2 C H CO C C OO H C O C OO -

A S C OR B A T E
OH H HOC H 2 C H C CO O

1.10.2.1 1.10.3.3
CO

OH OH H

S orbitol
2.7.1.3
H P OC H 2 C H C OH H C C C OO -

2. 7

CO

. 1.

HO OH

A DP

C HOHC H 2 NH 2 OC H 3

HN

P E N T O S E S

3-Dehydrogulonate
OH H HOC H 2 C H C OH C C HO

1.1.1.130
H

2, 3-Dioxogulonate
H C OH C C HO H HOC H 2 C H C

Dehydroas c orbate
C O C H 2 OH H H C OH C CO

.1 3 .1

.1 7

P -G luc ono lac tone

NADP +
5.3.1.8

OH

1.1.1.49

G luc os e-6-P
5.3.1.9

C H 2 OP O OH OH

I O

C H(OH)C OO OC H 3 OH

HO OH

Normetepinephrine
.3 .4

OH

C oumarate

C HOHC H 2 OH OC H 3 OH

(Normetadrenaline)

Dopaquinone P las toquinone

O O
NH

OH

I
OH

HOC H 2

OH H

OH OH H

L -Xylos e
OH H HOC H 2 C H C H C OH OH

4.1.1.34
C H 2 OH

D-A rabinos e
OH H HOC H 2 C H H C OH OH H C C OH CO

5.3.1.3

OH OH

D-R ibulos e
OH H P OC H 2 C H H C OH OH H C C OH C HO CO

2.7.1.47

HOC H 2 C

C H 2O P

OH OH H OH 6-P -G luc onate NA DP H

4-OH-3-MethoxyD-mandelate
C H 2O P O NHC OC H 2 NH 2 H 2C OC NH C HO NH RP

1 .4

4-OH-3-Methoxyphenylglyc ol
NH H 2C C

1.14.18.1

ME L A NIN

T HY R OXINE
OOC -C H-C H 2 C OO HNC O C N

L IG NIN

T annins
O C

P lant P igments

NADP +

OH OH H

F ruc tos e-1-P

C H 2 OH HOC H 2
H H H

1.1.1.44 5.1.3.1
H H C C O C H 2 OH H P OC H 2 C H C

H C

HO C C O C H 2 OH

2.2.1.1

P OC H 2 C

C H 2 OH

L -A rabitol
OH OH H HOC H 2 C H C H C OH C HO

L -Xylulos e
HOC H 2 C

2.7.1.53

NA DP H

L -Xylulos e-5-P
HOC H 2 C OH H

C H 2 OH P OC H 2

F ruc tos e-6-P ATP

C HO

OH OH H

HN

C HO NH RP

H 2N

HC C

N CH N

OOC

N C C CH N RP

N C C N CH RP O C C NH C N CH N RP

OH OH OH

C H 2 OH

R ibitol
H H C

G lyc inamideribos yl-P

6.3.4.13

OH

OH

2.1.2.2

6.3.5.3 6.3.3.1 F ormyl F ormyl 5-A mino 4.1.1.21 5-A mino-4-imidazole 6.3.2.6 5-A mino-4-imidazole 4.3.2.2 5-A minoimidazole c arboxylate-R P (N-s uc c inylc arboxamide)-R P c arboxamide-R P glyc inamide-R P glyc inamidine-R P imidazole-R P
H 2 NC ONH 2

RP

H2N

H 2N

CH

H 2N H 2N

RP

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

OH OH

1.1.1.10

OH H OH OH

L -A rabinos e
OH H HOC H 2 C H C H C OH OH

5 .3

.1 .4
HOC H 2

Xylitol
C H C H

2.7.1.47

D-Xylos e
OH OH P OC H 2 C H C H CO C H 2 OH

H C C HO

D-R ibulos e-5-P

5.1.3.1
H P OC H 2 C OH C C O C H 2 OH

3.1.3.11

2.7.1.11

HOC H 2 C

E rythros e-4-P
P OC H 2

OH OH

A DP
HO C C O C H 2O P C H 2O P O

Urea

H 2N
OC

C OO C N H H

NH 2 CO
NH

H2N
OC

OC C N H H

NH CO NH

HN OC

NH C C CO NH HN OC

O C NH

N C C CH NH HN HC

O C N

2.1.2.3
N C C CH NH

H2N HC O

H C

H C

3.5.3.4

C HO

C O C H 2 OH

D-R ibos e
5.1 .3. 4

OH OH OH

L -L yxos e

L -R ibulos e 2.7.1.16 L -R ibulos e-5-P

1 .1 .1
H OH C CO C H 2 OH

5.3.1.6

OH OH H

.9

HOC H 2

2 .7
2.7.1 .17

4.1.2.-

.1 .1

OH H

2.2.1.2

D-Xylulos e-5-P

F ruc tos e1: 6-bis -P

NH 2

.1 .4 2 .6 .1 0 .1 20 1 .4 1. 1.

G LY C INE
O

C H 2 (NH 3 )C OOH

A llantoate
NH 2

3.5.2.5

A llantoin
O O O HC

1.7.3.3
N NH 2 N

UR A T E
N CH N
N

N H

3. 2. 2.

Inos ine
2.4.2.1

3. 1. 3.

1.1.1.204 1.1.3.22 Hypoxanthine 1.1.3.22 Xanthine

F ormylamidoimidazolec arboxamide-R P
3.5.4.10
HN O C N N C C N CH RP HC

N O P O O
HC

N
CH

OH H

D-Xylulos e
H+
PHOTOSYSTEM II

OH OH H H C H C C HO P OC H 2

H+

H+

c otophosphoryla SYSTEM n-cycli electr 2H+ yclic Ph tion l No (electric curre on fl C nt) o H+ 2H+

PHOTO- H+

P OC H 2 C

H C

H C

H OH C C C O C H 2O P

P -R ibos yl amine
4.1.2.13

G lyoxylate

S arc os ine

2. OOC C H 2 NHC H 3

N C H2 O

-O P ~O P ~O P O C H 2 O O O O

NH 2 N C C CH C HC N R P (P ) N

OOC -C H-C H 2 C OO

F umarate

OH

1.5.99.2
OOC C H 2 N(C H 3 ) 2

C yc lic A MP
1.4.4.2

4.6 .1. 1

ATP
d-A DP
2.7.4.6

2.7.4.6

OH OH

A DP

2.7.4.3 2.7.4.4

A DE NOS INE -P
(A MP )

4.3.2.2

NH N C C N CH C HC NH R P N

A s partate
6.3.4.4 3.1.4.6 2.4.2.1

INOS INE -P
(IMP )
HN O C N N C C CH N RP

1.17.4.1

A denylos uc c inate
3. 5. 4. 3

A denine
2.7.7.7

1.1.1.205

OC

OH OH OH

Dimethylglyc ine
2.1.1.5
OOC C H 2 N(C H 3 ) 3
+

3 3

H 2O
H+ H+

Translocated protons

O2

H+
H+

2 2

H+

H+
H+

THYLAKOID LUMEN

H+

THYLAKOID MEMBRANE STROMA CHLOROPLAST OUTER MEMBRANE

C OO

L inoleate
1.3.1.35

1.14.99.25
C OO

-L inolenate

A rac hidonate
C O-S -AC P

L I P I D B I O S Y N T H E S I S

C OS C oA

1.14.99.5

Oleoyl-C oA S tearoyl-C oA
C H 3 (C H 2 ) 14 C OS -AC P C OS C oA

P almitoleoyl-A C P Dehydros tearoyl-C oA P almitoyl-C oA

1.3.1.9 2, 1.3.1.10
C H 3 (C H 2 ) n C H=C HC OS -C oA C H 3 (C H 2 ) 14 C OS C oA C H 3 (C H 2 ) 14 C H=C HC OS -C oA

P almitoyl-A C P A C Y L -A C P
C H 3 (C H 2 ) 6 C H 2 C H 2 C OS AC P

3-E noyl-A C P

4.2.1.60 4.2.1.61

Dec anoyl-A C P

1. 3. 1.

3, 4-Dec enoyl-A C P
9

C H 3 (C H 2 ) 5 C H=C HC H 2 C OS AC P C H 3 (C H 2 ) 6 C H=C HC OS AC P

4. 2. 1.

2, 3-Dec enoyl-A C P 2, 3-Hexenoyl-A C P

C H 3 C H=C HC O-S -AC P C H 3 (C H 2 ) 2 C H=C HC O-S -AC P

4 .2 .1

C H 3 (C H 2 ) 2 C H 2 C H 2 C OS AC P

Hexanoyl-A C P

1.3.1.9

4.2.1.59

C H 3 C H=C HC O.S -AC P

C H 3 C H 2 C H 2 C OS AC P

B utanoyl-A C P

1.3.1.9

C rotonoyl-A C P
R -C H 2 C OO

4.2.1.58

A C Y L -C oA
(C ytos ol)
2.3.1.7

C H 3 (C H 2 ) n+2 C OS -C oA

6.2.1.3

3.1.2.20

F A T T Y A C ID

L I P I D D E G R A D A T I O N

C arnitine O-A c yl-c arnitine

O-A c yl-c arnitine
3.1.1.28
C H 3 (C H 2 ) n C H 2 C H 2 C OS C oA

3.1.1.3

C H 2 O-C O-R C H 2 O-C O-R "

R -C O-OC H

C H 2 O-C O-R R -C O-OC H

T riac ylglyc erol

FAT

2.3.1.20 glyc erol 3.1.3.4 2.7.1.107

Diac yl

C H 2 OH

A C Y L -C oA
(Mitoc hondria)

1.3.99.3 1.3.99.3 1.3.99.2

C H 3 (C H 2 ) n C H=C HC OS C oA C H 3 (C H 2 ) 2 C H=C HC OS C oA

2, 3-E noyl-C oA

4.2.1.17 4.2.1.17 4.2.1.55

C H 3 (C H n C H(OH)C H 2 C OS C oA

C H 3 (C H 2 ) 2 C H 2 C H 2 C OS C oA

Hexanoyl-C oA B utanoyl-C oA
C H 3 C H 2 C H 2 C OS C oA

2, 3-Hexenoyl-C oA C rotonoyl-C oA P entenoyl-C oA

C H 2 O-C O-R C H 3 C H 2 C H=C HC OS C oA C H 3 C H=C HC OS C oA

3-OH-Hexanoyl-C oA 3-OH-B utanoyl-C oA 3-OH-P entanoyl-C oA

C H 2 O-C O-R C H 3 C H 2 C H(OH)C H 2 C OS C oA C H 3 C H(OH)C H 2 C OS C oA

C H 3 (C H 2 ) 2 C H(OH)C H 2 C OS C oA

Odd C F atty ac ids

P entanoyl-C oA
C H 2 O-C O-R R '-C O-OC H O C H 2 O-P O O

C H 3 C H 2 C H 2 C H 2 C OS C oA

OH

OH

R '-C O-OC H

1.3.99.7
HO OH OH

P hos phatidyl inos itol

P HOS P HA T IDY L S E R INE

O

C OO O + C H 2 O P O C H 2 C HNH 3

R '-C O-OC H

2.7.8.8 2.7.8.11
C H 2 O-C O-R

S erine

Inos itol
R '-C O-OC H

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

C H 2 O-C O-R R '-C O-OC H

4.1.1.65

C H 2 O-C O-R R '-C O-OC H O

O HC O-C O-R

+ C H 2 OP O C H 2 C H 2 N(C H 3 ) 3 2.1.1.17 O C H 2 OC H=C HR 2.1.1.71 C H 2 O-C O-R R -C O-OC H O 3.1.1.32 O R '-C O-OC H + + C H 2 OP O C H 2 C H 2 N(C H 3 ) 3 C H 2 OP O C H 2 C H 2 N(C H 3 ) 3 O O

P hos phatidyl ethanolamine C E P HA L IN

O

O + C H 2 O P OC H 2 C H 2 NH 3

C H 2 O-P O C H 2 C H(OH)C H 2 O-P -OC H 2 O O

C ardiolipin

OP hos phatidylglyc erol

2.7.8.1

C DP -E thanolamine
C H 2 O-C O-R HOC H O

+ C P P - OC H 2 C H 2 NH 3

2.7.7.14

E thanolamine-P
C H 2 OH HOC H O + C H 2 OP O C H 2 C H 2 N(C H 3 ) O

- L ys olec ithin

3.1. 1.5

G lyc erophos phoc holine

3.1.4.4 3.1.4.3
+ OC H 2 C H 2 N(C H 3 ) 3

C holine plas malogen 1.3.1.35 S erine + NH

2.3.1.50
3 C H 3 (C H 2 ) 14 C OC HC H 2 OH

L E C IT HIN

+ C P P -O C H 2 C H 2 N(C H 3 ) 3

2.7.8.2

C DP -c holine
.3

Dehydros phinganin G anglios ides

+ NH 3 C H 3 (C H 2 ) 14 C H(OH)C HC H 2 OH

1.1.1.102

S phinganin

+ NH 3 C H 3 (C H 2 ) 12 C H=C HC H(OH)C HC H 2 OH

2 .7 .8

3.1 .4. 12

4-S phingenin
3.5.1.23
NHC OR

2.4 .1. 62

UDP -S ugars A c yl-C oA

NHAcyl O + C H 3 (C H 2 ) 12 C H=C HC H(OH)C HC H 2 O P O C H 2 C H 2 N(C H 3 ) 3 O

S P HING OMY E L IN

2.7.8.3

C H 3 (C H 2 ) 12 C H=C HC H(OH)C HC H 2 OH

3.1.4.12

C eramide

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

L yc opene -C A R OT E NE
C OO -

(C 40)

T o B rain V IS ION
(C 40)

hv R hodops in
C H 3O C H 3O O O C H3 n

Metarhodops in
1.13.11.21

Ops in
C HO

R etinoate
1.2.1.36 1.1.1.105

(C oenzyme Q)
5.2.1.3

Ubiquinone

trans -R etinal

L ight

11-c is -R etinal
1.1.1.105

C HO

Menaquinone P las toquinone

O HO
CH3 O

R etinol es ters
2.3.1.76 3.1.1.21

C H 2 OH

CH3
O C H3

(V itamin A )

(V itamin K )

(V itamin E )

6.

trans -R etinol S T E R OIDS P roges terone

HO H

5.

5.2.1.7

Dark

11-c is -R etinol

C H 2 OH

P hylloquinone

-T oc opherol

2.5.1.21

F6

N2

3.

HO

HO H

H HO H

1.9.3.1

P regnenolone

C HOL E S T E R OL

Des mos terol

C OO C H2

Zymos terol

L anos terol

5.4.99.7 1.14.99.7

S qualene
(C 30)

1/ O 2 2

IV

HE MOG L OB IN
C H2 CH H 3C HC N H3C C H2 C H2 C OO C H H C N Fe N C H3 C H2 C H2 C OO H 3C CH C H3 CH CH H 3C

C HL OR OP HY L L
C H2 CH H2 C N H H C H2 C H2 N C H3 C H2 C H2 C OO H 3C C H3 C H 2 CH H3C
H 2C

C OO C OO H2 C N H H C H2 N C H3 C H2 C H2 C OO C H3 C H2 C H2 C H2 - OOC
H 2C H 2C

C H2 N H N H

C H2 C H2 N H N
H 2C

C OO H2 C N H H N C H2 C H2

C OO C H2

COOCH2

H2O
TR A NS L O

Pi AD P + H+ H+ H+ H+ H+

P +1 P i

T A

N H N H

H2C

C H2 C H2 C OO -

C H2 C H2 C OO -

HE ME

1.3.3.4 4.99.1.1

P rotoporphyrinogen

1.3.3.3

C oproporphyrinogen

2003 International Union of Biochemistry and M olecular Biology

www.iubmb.org

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+

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

Ferredoxin

D-R ibos e-5-P

2eQB QA
Pheophytin P680 Chl.a Mn
2e-

PQ PQH2 PQH2

_ PQ
1e-

2e-

*2e
Fe-S

H+

S edoheptulos e-P P
2.2.1.1
P OC H 2C HOHC HO

OH OH OH H

2 .7 .7

.7

DNA R NA
O C

H+

d-A T P
2.1.2.1

2. 7. 7. 7

d-G T P d-C T P GTP T T P 2.7.4

2 .7 .7 .6

2.4.2.15

d-G DP
2.7.4.6

XA NT HOS INE -P
(XMP )
2. 4. 2. 1
6.3.4.1 6.3.5.2
HN H 2N C O C N N C C CH N RP

P U R I N E S

1 .1

B etaine
1.2.1.8
+

2 .7
2.7.7.6

7 .4

1e-

PQ

Cyt bf
2e-

H+
H+ H+

NADP+

A1 Chl.A0
PC

2PQH2

Cyt bc _ 2e2PQ 2PQ

NADPH+H+
H+ H+ H+

Dihydroxyac etone-P
(G lyc erone-P )

HOC H 2 C OC H 2 OP

2.2.1.1

3-P -G lyc eraldehyde

5 .3 .1 .1 .1 5 .3 .1 2.7.1.28

Pi

Pi NA D+
1.2.1.12

2.4.2.14 6.3.4.7

OHC C H 2 N(C H 3 ) 3

B etaine aldehyde
1.1.99.1

F OL IC A C ID C1 P OOL
4.1.2.5

ATP
4. 2. 1. 20

2.7.7.6

.7 .7

.1

G uanine G DP

2.7.4.8

2 .7

.7 .6
O C

.6

1. 17 .4

.1
O C

G UA NOS INE -P
(G MP )
NH 2 C CH N CH OC N DP

2e-

P700
PC PC

Pi
A DP
1

ADP
Pi

Fe-S 2e- Cyt.f

Glyceraldehyde

+ HOC H 2 C H 2 N (C H 3) 3

C H3 H 2 NC H 2 C HC OO

C H3 H 2 NC ONHC H 2 C HC OO

HN OC

C H-C H 3 CH2 NH

HN OC

4H +

Ribulose-1,5-bis-P

1.2.1.13
C H 2O P O

C HOL INE
2.6.1.51 1.4.1.7

ATP

Fixation

CO2

NA DH

HOC H 2 C H(NH 3 )C OO

3-A minois obutyrate

3.5.1.6

S E R INE

4.2.1.22 4.1.1.11
H 2 NC H 2 C H 2 C OO

2. 1

-Ureido is obutyrate
. 1. 13
3.5.1.6

3.5.2.2

Dihydro thymine
3.5.2.2

C C H3 CH NH O C

T DP
2.4.2.4
O C

2 .7

.4 .9 HN

OC

C -C H 3 CH DP

2.1.1.45

HN OC

1.3.1.2

T hymine
HN OC

T HY MIDINE -P
2 .4 .2 .4

d-UMP
N

CH CH N DP 3.5.4.12 NH 2 C CH CH OC NH O C

d-C MP

2.7.4.14

d-C DP

HN
H 2 NC ONHC H 2 C H 2 C OO OC

2.7.6.1
OH OH

OP OP

1: 3-bis -P -G lyc erate

A DP
2.7.2.3

P OC H 2C HOHC OO P

HOC H 2 C OC OO

-A lanine
-OOC NH

ATP
ATP synthase
3.6.1.34

ATP
HO C OO

P -R ibos yl-P P

Hydroxypyruvate

3.1.3.3

C arbamoyl -alanine
HN OC O C NH

Dihydrourac il
HN OC O C

C H2 C H2 NH

1.3.1.2

N H

CH CH

1.17.4.1

Urac il
O C

3.5.4.1
O C HN OC

C ytos ine
CH CH

NH 2

C DP

A DP

+ P OC H 2 C H(NH 3 )C OO

2 C H2 OC C H-C OO N

C H2 C H-C OO

P hos phos erine

2.6.1.52

C arbamoyl as partate
2.6.1.22
H P OC H 2 C H C H C H C

3.5.2.3

UR IDINE Dihydro Orotate Orotidine-P Uridine-P UDP 4.1.1.23 (UMP ) 2.7.4.4 2.4.2.10 2.7.4.6 triphos phate orotate 1.3.1.14
(UT P )
H P OC H 2 C H C H C H C NH 2 N OC C NH CH C HC N N H P OC H 2 C H C CO C H2 C ONH 2 NH C C HC N N CH N RP

CH C -C OO NH

HN

CH

C -C OO OC N RP

CH OC N C H RP HN

2.4.2.9

N OC

N R PPP

C H 2.7.4.6 CH

6.3.4.2

RPPP

C Y T IDINE triphos phate

(C T P )
H H C C C H CH N

P Y R I M I D I N E S

a
c

C OO

HO

ATP
OH C OO HO O OH

1.1.1.29
NH 2 N + C C N CH C HC N N R P (P P )

1.13.11.34
O

5. 1 .1 3 . 9 9 4 .9 . 3 9 .1

L eukotriene B 4
C OO

3-P -G lyc erate

2.7.1.31

P OC H2C HOH C OO

1.1.1.95

P -Hydroxypyruvate
2.4.2.17
HC N

P OC H 2 C OC OO

OH OH O

P -R ibos yl-A T P
C

3.6.1.31

P -R ibos yl-A MP
C CH NH + C H 2 C H(NH 3 )C OO

3.5.4.19

OH OH O

OH OH

P OC H 2 C

P ros taglandin P G E2
C H 3 (C H 2 ) 14 C H(OH)C H 2 C OS -C oA

HO

OH

5.3.99.5

T hromboxane B 2 Oxos tearoyl-C oA

Mitoc hondrial
C H 3 (C H 2 ) 14 C OC H 2 C OS -C oA

OH-S tearoyl-C oA

2, 3-Diphos phoglyc erate

P OC H2 C H(O P ) C OO

5.4.2.1

HOC H2C H(OH) C OO

G lyc erate

C C H 2 C HC OO NH NHC OC H 2 C H 2 NH 2
H

HC N

C arnos ine
4.1.1.22

HC N CH

C NH

P -R ibulos ylformimino P -R ibos ylformimino 5-aminoimidazole- 5.3.1.16 5-aminoimidazolec arboxamide-R P c arboxamide-R P + +

+ C H 2 C H(NH 3 )C HO HC N C C H 2 C H(NH 3 )C H 2 OH HC N C

RP

OH OH HN

Imidazole glyc erol-P

HC N C H C NH C H 2 C OC H 2 OP

C H 2 C H(NH 3 )C H 2 OP

C H 3 (C H 2 ) 14 C OC H 2 C OS -C oA

E ndoplas mic R etic ulum C hain elongation

C H 3 (C H 2 ) n C H(OH)C H 2 C OS AC P

ACE TATE

C H 3C OO

HIS T IDINE
4.3.1.3

1.1.1.23

His tidinal
OOC HN

1.1.1.23

His tidinol
OC N

NH CH

3.1.3.15

His tidinol-P

NH CH

4.2.1.19

2.6.1.9
CH N C

3-OH-A c yl-A C P

1.1.1.100

3-Oxoac yl-A C P

C H 3 (C H 2 ) n C OC H 2 C OS AC P

2-P -G lyc erate

4.2.1.11

HOC H2C H(O P ) C OO

Imidazole ac etol-P
CH C HC OO

HC

C C H NH

C H 2 C H 2 NH 2

1.2.1.4
C H 3 C H 2 OH

C HC H 2 C H 2 C OO NH CH

C HC H 2 C H 2 C OO NH CH

HIS T A MINE

2.3.1.41

E T HA NOL
1.1.1.1

2.1.3.2

2 .3

F ormimino glutamate

3.5.2.7

Imidazolone propionate

4.2.1.49

NH CH

4.3.1.3

Uroc anate 2SO 4

1.2.1.32

60 C H 3 (C H 2 ) 6 C H(OH)C H 2 C OS AC P

.6 0

3-OH-Dec anoyl-A C P
C H 3 (C H 2 ) 2 C H(OH)C H 2 C OS AC P

1.1.1.100

3-Oxo-Dec anoyl-A C P
2.3.1.41
C H 3 (C H 2 ) 2 C OC H 2 C OS AC P

C H 3 (C H 2 ) 6 C OC H 2 C OS AC P

.1 .3

+ C H 2 C O-OC H 2 C H(NH 3 )C OO

A c etyls erine
+ S -C H 2 C H(NH 3 )C OO + S -C H 2 C H(NH 3 )C OO

HS
.9 9

3-OH-Hexanoyl-A C P
C H 3 C H(OH)C H 2 C OS -AC P C H 2 OH HOC H C H 2 OH

1.1.1.100

3-Oxo-Hexanoyl-A C P
C H 3 C OC H 2 C OS AC P

P -enolpyruvate
A DP Malonyl-A C P
2.3.1.39
HOOC C H 2 C O-S -AC P

C H 2 =C (O P ) C OO

1.8.99.1

HS O -

1.8.99.2

A c etaldehyde HS
4 .1 .1 .1

C H 3 C HO

P hos phoadenylyls ulphate

(P A P S )
4.2.1.22 4.4.1.8

2.7.1.25

A denylyls ulphate
(A P S )

2.7.7.4

4 .2

+ .8 HS C H 2 C H(NH 3 )C OO

2.3.1.41

C Y S T INE
4.4 .1.1 5

1.6.4.1

C Y S T E INE

4.4.1.1 4.2.99.9

+ C H 2 C H(NH 3 )C OO + S C H 2 C H 2 C H(NH 3 )C OO

C ys tathionine

+ HS C H 2 C H 2 C H(NH 3 )C OO

+ C H 3 S C H C H C H(NH )C OO 2 2 3

Homoc ys teine
3.3.1.1

2.1.1.13 2.1.1.14

ME T HIONINE
+ C H 3 S C H C H C H(NH )C OO 2 2 3 +

3-OH-B utanoyl-A C P
HOC H

1.1.1.100 1.1.1.8

C H 2 OH C H 2O P

A c etoac etyl-A C P
2.3.1.41

1.13.11.20
+ HO 2 S C H 2 C H(NH 3 )C OO + HO 3 S C H 2 C H(NH 3 )C OO

2.7.1.40

G lutamate
.1 .2
6 .3 .2 .2

Adenos yl

Adenos yl

2.5.1.6

G lyc erol
2.3 .1.1 5

2.7.1.30

3-P -G lyc erol

2.3. 1.51
C H 2 O-C O-R

K E TONE B ODIE S A c etone 3-OH-B utyrate

C H 3 C OC H 3 C H 3 C H(OH)C H 2 C OO

3 .7

.1 .2

ATP

4.4 .1. 15

HS O 3
+ C H 3 C H(NH 3 )C OO

R -C O-OC H C H 2O P

2.7.8.5

Malonyl-C o-A A c etyl-A C P

2.3.1.38
C H 3 C O-S -AC P

HOOC C H 2 C O-S C oA

P Y R UV A T E
1.2.4.1 2.3.1.12 1.8.1.4

1.4.1 .1

2.6.1.2

3-S ulphinyl pyruvate

4.1.2.5
+ C H 3 C H(OH)C H(NH 3 )C OO

HO 2 S C H 2 C OC OO

C ys teine s ulphinate

C ys teate

4 .1

A L A NINE

4.1.1.29

Hypotaurine

HO 2 S C H 2 C H 2 NH 2

1.8.1.3

HO 3 S C H 2 C H 2 NH 2

C H 2S H + OOC C H(NH 3 )C H 2 C H 2 C ONHC HC OO

S -A denos yl homoc ys teine

+ S C H 2 C H 2 C H(NH 3 )C OO

2.1.1.10 2.1.1.20

S -A denos yl methionine
(S A M)

T aurine

-G lutamylc ys teine
6 .3 .2 .3

G lyc ine

4.1.1.4

1.1.1.30

P hos phatidate

A c etoac etate
3.1.2.11

C H 3 C OC H 2 C OO

4.1.1.9

4. 1. 3.

18

+ OOC C H 2C H 2 C OO C H 2 C H 2 C H(NH 3 )C OO

4.1.1.12 2.6.1.18
C H 3 C H(OH)C OO

S uc c inylhomos erine
2.3.1.46
C H3 C H3

C H 2S H + OOC C H(NH 3 )C H 2 C H 2 C ONHC HC ONHC H 2 C OO

1 .1
CH3COCOO-

.1 .2

T HR E ONINE Malonic s emialdehyde

OHC C H 2 C OO -

P Y R UV A T E
3-OH-A c yl-C oA
1.1.1.35 1.1.1.35
C H 3 (C H 2 ) n C OC H 2 C OS C oA

LACTATE
4. 2. 1. 52
1.2.1.18
4.1.1.32

4. 1. 3.

18

O-P hos pho4.2.99.2 homos erine

C OO

+ P OC H 2 C H 2 C H(NH 3 )C OO

Homos erine 2.7.1.39

1.1.1.3
C H3 C H3

+ HOC H 2 C H 2 C H(NH 3 )C OO

B ile A c ids
HC HO
4.1.2.12
C H3 + C HC H(NH 3 )C OO C H3

G lutathione

HOC H 2 C (C H 3 ) 2 C OC OO

Oxopantoate

3-Oxoac yl-C oA

2. 3. 1.
2. 3. 1.

16

3-Oxohexanoyl-C oA A c etoac etyl-C oA

C H 3 C H 2 C OC H 2 C OS C oA C H 3 C OC H 2 C OS C oA

C H 3 (C H 2 ) 2 C OC H 2 C OS C oA

16

NA D ATP C O2
6.4.1.1

1.2.4.1 2.3.1.12 3.1.3.43

HOH GDP C O2 GTP

4.2.1.16
C H 3 C H 2 C OC OO

C (OH)C H(OH)C OO

C HC OC OO

1.1.1.169

2-A c etolac tate Oxobutyrate

4 .1 .3 .1
C H3 HOC H 2 C HC OO

C H 3 C OC (OH)C H 3

1.1.1.86

2-3-Dihydroxy is ovalerate
C H3

4.2.1.9

2-Oxo- 1.4.1.8 V A L INE is ovalerate

C H3 C H3

2.6.1.32

1.1.1.157

2.3 .1.9

1.2.1.25

P antoate -A lanine 3.5.1.22

6.3.2.1

HOC H 2 C (C H 3 ) 2 C H(OH)C OO

NADH+H+
CH3COSCoA

1.1.1.35

3-Oxopentanoyl-C oA
OHC C OO

4.1.3.5

NAD+
2.6 .1.4 2.6 .1.4 4
1.1.1.39

A C E T Y L -C oA

Methylmalonyl s emialdehyde
2. 3. 1. 16

C H3 OHC C HC OO

1. 1. 1.

31

3-Hydroxyis obutyrate
C OO C H 3 C OC (OH)C H 2 C H 3

3.1.2.4

3-Hydroxy- 4.2.1.17 Methyl 1.3.99.3 Is obutyryl-C oA Is obutyryl-C oA ac rylyl-C oA

C H3 C (OH)C H(OH)C OO C H3 C HC OC OO C H 3C H 2 CH3 + C H C H(NH 3 )C OO

HOC H 2 C HC OS -C oA-

C H 2 = C C OS C oA

C H 3 C HC O-S C oA

HOC H 2 C (C H 3 ) 2 C H(OH)C O NHC H 2 C H 2 C OO

P A NTOT HE NA T E
2.7.1.33

P OC H 2 C (C H 3 ) 2 C H(OH)C O NHC H 2 C H 2 C OO

O O

2.7.7.41

G lyoxylate
1.1.1.79 1.2.3.5
HOC H 2 C OO

4.1.3.5
C H 2 C OO C H 3 C (OH)C H 2 C OS C oA

4.1.3.4

C H 2 O P OC MP

NA DH+H +
4. 2. 1. 18

-OOCCOCH COO2

OX A L OA C E T A T E
NAD+
4.1.3.7 4.1.3.8

2.6.1.1
CH2COOC(OH)COOCH2COO-

C DP -diac yl glyc erol

O

G lyc olate
1.2.1.21 2.7.8.5
HOC H 2 C HO

-OH--Methylglutaryl-C oA
1.1.1.34

4.2.1.9 2-A c eto-22-Oxo-3-methyl 2: 3-Di-OHhydroxy- 1.1.1.86 3-methylvalerate valerate butyrate

C H3 CH3 C H 3 C OC HC OS C oA C H 3 C H(OH)C HC OS C oA C H3 C H 3 C H=C HC OS C oA

C H 3C H 2

2.6.1.32

C H 3C H 2

IS OL E UC INE
CH3

C OO P OC H 2 C (C H 3 ) 2 C H(OH)C O NHC H 2 C H 2 C O NHC HC H 2 S H

4-P -P antothenate C ys teine 6.3.2.5

1.2.1.25

4-P -P antothenylc ys teine

4.1.1.36

C H 2 O-C O-R C H 2 O-P O C H 2 C HOHC H 2 OH

HOOC -C OOH

Oxalate

F MN
I

I
1.1.1.37

C IT R A T E
4.1.3.2

G lyc ol aldehyde
1.4.3.8
+ HOC H 2 C H 2 NH 3

C H 2 C OO C H 3 C (OH)C H 2 C HO

Glyoxylate Cycle

-OOCCHO

4.2.1.3
CH(OH)COO CHCOOCH2COO-

P ropanoyl-C oA
2.1.3.1 4.1.1.41 5.1.99.1
C H3 OOC -C H-C OS C oA

C H 3 C H 2 C OS C oA

2-Methylac eto2-Methyl-3-4.2.1.17T iglyl-C oA 2 Methylbutyryl1.1.1.35 1.3.99.3 ac etyl-C oA hydroxyC oA butyryl-C oA

C OOH

C H 3 C H 2 C HC OS C oA

P OC H 2 C (C H 3 ) 2 C H(OH)C O NHC H 2 C H 2 C O NHC H 2 C H 2 S H

4-P -P antetheine
2.7.7.3

1.6.5.3

6.4.1.3

+ P OC H 2 C H 2 NH 3

Mevaldate
1.1.1.32
C H 2 C OO

F MNH 2
2H
+
4.1.3.1
CH3CH(OH)CH2CO.SCoA

C OOH

IS OC IT R A T E
1.1.1.41

(C H 3 ) 2 C HC (OH)C H 2 C OO

2.7 .1. 82

E thanolamine
C H 3 C OC H 2 C H 2 N(C H 3 ) 3

2F e -S (5 C lusters)

2-Is opropylmalate
4.2 .1. 18
4.2.1.18 1.1.1.3

3-Is opropyl- 1.1.1.85 Oxoleuc ine 4.2.1.33 malate

C H3

(C H 3 ) 2 C HC HC H(OH)C OO

(C H 3 ) 2 C HC H 2 C OC OO

2.6.1.6 1.4.1.9

+ (C H 3 ) 2 C HC H 2 C H(NH 3 )C OO

L E UC INE
1.2.1.25

ADP - OC H 2 C (C H 3 ) 2 C H(OH)C O NHC H 2 C H 2 C O NHC H 2 C H 2 S H

Dephos pho-C oenzyme A

2.7.1.24

A c etylc holine
.4 .2
2.3.1.6

3 .1

C H 3 C (OH)C H 2 C H 2 OH

4H+

Mevalonate
2.7.1.36 2.7.4.2
C H 2 C OO

1.6. 5.3

MA L A T E 4H+ 2H+ 4.2.1.2

or 2H+ -

-OOCCOCH CH COO2 2

G L UT A R A T E
1.2.4.2 2.3.1.61

2-OXO -

4.1.1.71

Methylmalonyl-C oA
2 .7 .2 .4

AS PAR TATE
4.3.1.1 6.3.5.4

3-Methylglutac onyl-C oA
H C N

OOC C H 2 C = C HC OS C oA

6.4.1.4

3-Methylc rotonyl-C oA
H2 C
N

C H3 C H 3 C = C HC OS C oA

1.3.99.10

Is ovaleryl-C oA

(C H 3 ) 2 C HC H 2 C OS C oA

P -ADP - OC H 2 C (C H 3 ) 2 C H(OH)C O NHC H 2 C H 2 C O NHC H 2 C H 2 S H

C oenzyme A
+ NH 3 OOC C H-C H 2 C H 2 C H 2 C HC OO + NH 3

2.7.7.15

C holine-P

+ HOC H 2 C H 2 N(C H 3 ) 3

2.7.1.32

C HOL INE

UQH 2

F UMA R A T E
F ADH 2
F e-S C yt.b
1.3.5.1

OOCCH=CHCOO-

+ P OOC C H 2 C H (NH 3 )C OO

A s partyl-P

1 .2

.1 .1

+ NH 3 C H 3 (C H 2 ) 12 C H=C HC H(OH)C HC H 2 O- G alac tos e

C H 3 C (OH)C H 2 C H 2 O P P

Diphos phomevalonate

S UC C INY L -C oA
6.2.1.4

-OOCCH2CH2CO.SCoA

5.1.99.1 5.4.99.2

1.2.1.16

P s yc hos ine
NHC OR

2.4.1.23

UDP -G alac tos e

A c yl-C oA
C H2

UQ
4.1.1.33

F AD

II

S UC C INA T E

-OOCCH2CH2COO-

OOC C H 2 C H 2 C HO A s partyl 4.2.1.52 2, 3-DihydroP iperideineN-S uc c inylS emialdehyde dipic olinate 2, 6-dic arboxylate 2-amino-6-oxoS uc c inic pimelate s emialdehyde OH + (C H 3 ) 3 NC H 2 C H(OH)C H 2 C OO

+ OHC C H 2 C H (NH 3 )C OO

HC OOC C

C H2 C H-C OO

H 2C OOC C

C H2 C H-C OO

OOC C H 2 C H 2 C ONH OOC C H 2 C H 2 C ONH OOC C OC H 2 C H 2 C H 2 C H-C OO OOC C HC H 2 C H 2 C H 2 C H-C OO + NH 3

A M I N O A C I D S

1.3.1.26

2.6.1.17

N-S uc c inyl-2, 63.5.1.18 Diaminodiaminopimelate pimelate

+ H 2 N(C H 2 ) 4 C H(NH 3 )C OO

Glycine
2.3.1.37

UQH 2
C H 3 C -C H 2 C H 2 O P P

2H+

+ H 2 NOC C H 2 C H (NH 3 C OO

C arnitine

+ + (C H 3 ) 3 N(C H 2 ) 3 C H 2 C H(NH 3 )C OO

C H 3 (C H 2 ) 12 C H=C HC H(OH)C HC H 2 O- G alac tos e

3.2.1.46 2.4.1.47 1.3.99.7

C erebros ide
C H3

Is opentenyl-P P
(C 5)

1.10.2.2

2UQH 2

UQH 2 1e_ UQ.

5-A minolevulinate

A s paragine

1.14.11.1

2.6.1.19 1.3.99.7
OOC C H 2 C H 2 C H 2 C OS C oA

N 6 -T rimethyl3-OH-lys ine

+ + (C H 3 ) 3 N(C H 2 ) 3 C H 2 C H(NH 3 )C OO

1.14.11.8

N 6 -T rimethyllys ine

LY S INE

.7 5 .1 .1 20 4. 1. 1. 1.5.1.7 - 10

P hytoene
(C 40)
2.5.1.32

Dimethylallyl-P P
(C 5)
2.5.1.1
CH3 C H3

C H 3 C = C HC H 2 O P P

4H+

2.5.1.29

C H 3 C = C HC H 2 C H 2 C = C HC H 2 O P P C H 2O P P

G eranyl-P P
(C 10)
2.5.1.10

2e- 2UQ _ . III 2eF e-S C yt.bL C yt.c 1 2UQ

1.10.2.2

2H+
TR A

2-A MINO A C ID
R -C O-C OO

+ R -C H(NH 3 ) C OO

4.1.1.70

G lutaryl-C oA

OOC C H 2 C H 2 C H 2 C OC OO

2-Oxoadipate

+ OOC C H 2 C H 2 C H 2 C H (NH 3 ) C OO

4-A minobutyrate
(G A B A )
H 2 N(C H 2 ) 3 NH (C H 2 ) 4 NH (C H 2 ) 3 NH 2

OOC C H 2 C H 2 C H 2 NH 2

2.6.1.39

2-A minoadipate 1.2.1.31 2-A minoadipate s emialdehyde

A denos yl
+

+ OHC C H 2 C H 2 C H 2 C H (NH 3 ) C OO

C OO NH C HC H 2 C H 2 C OO

+ C H 2 C H 2 C H 2 C H 2 C H (NH 3 ) C OO

1.5.1.9

S ac c haropine

C H 3 -S C H 2 C H 2 C HNH 2

2-OXO A C ID
2.6.1.-

1eC yt.bH UQ

+ OOC C H 2 C H 2 C H (NH 3 ) C OO

MI

4.
2. 7. 2.

1.

1.

15

S permine

S -A denos ylmethyl thiopropylamine

(Dec arboxylated S A M)
B ios ynthes is Degradation

L E G E ND
C arbohydrates A mino A c ids
B ios ynthes is Degradation

NS

NA

G eranyl-geranyl-P P
(C 20)

T IO N

G L UT A MA T E
1.4.1.14

11 P OOC C H C H C H (NH ) C OO 3 2 2

2.5.1.22
H 2 N(C H 2 ) 4 NH (C H 2 ) 3 NH 2

G lutamyl-P
1.2.1.41

S permidine

P hytol
C H3

(C 20)

C H 2 OH

OPP C H2

C yt.c

1.4.1.2

3.5.1.2 6.3.1.2
+ H 2 NOC C H 2 C H 2 C H (NH 3 ) C OO

L ipids
2.5.1.16
H 2 NC H 2 C H 2 C H 2 C H 2 NH 2

F arnes yl-P P
(C 15)

C uA C uA
Heme a

+-

n tra

ting A s por . 6 . 1 . 3 T P s y 4 nth 3 os cp

NO 3 1.6.6.1 1.7.99.4

2H+

NO 2 -

F1

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

+ NH 4

ATP C O2

G lutamine

+ OHC C H 2 C H 2 C H (NH 3 ) C OO

B ios ynthes is Degradation

P urines & P yrimidines

B ios ynthes is Degradation

G lutamic s emialdehyde
2.6.1.13

P utres c ine
C H2 C H2 CH N C HC OO

as

6.3.5.5

P yruvate G lyoxylate
4.1.3.16
OOC C H(OH)C H 2 C OC OO

C H 3 C OC OO

OHC C OO

V itamins C o-enzymes & Hormones

B ios ynthes is Degradation

2H+ C uB Heme a 3
2e-

2H +

AT P
AD

C arbamoyl-P
2

H 2 NC OO P

ATP

+ H 2 NC ONHC H 2 C H 2 C H 2 C H (NH 3 ) C OO

P entos e P hos phate P athway P hotos ynthes is Dark R eac tions

Human Metabolis m is identified as far pos s ible by black arrows

C IT R UL L INE
2.1.3.3

P yrroline-5c arboxylate
4.1.1.17 1.5.99.8 C H2 1.5.1.2
C H2 C HC OO

2.1.3.3
+ H 2 NC H 2 C H 2 C H 2 C H (NH 3 ) C OO

C H2

4-Hydroxy2-oxoglutarate
2.6.1.23

B ios ynthes is

Degradation

F1

H+ H+

OR NIT HINE
F0
H+

NH

6.3.4.5
OOC C HC H 2 C OO N + H 2 NC NHC H 2 C H 2 C H 2 C H (NH 3 ) C OO

P R OL INE
1.14.11.2
HOC H H 2C N H C H2 C HC OO

C OMP A R T ME NT A T ION
T he "B ackbone" of metabolis m 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 s panning the MIT OC HONDR IAL INNE R ME MB R ANE

H 2 NC ONH 2

+ OOC C H(OH)C H 2 C H(NH 3 )C OO

2.1.4.1

UR E A

C H2 C H2 C H2 C H2 C H2 C OO -

CH2 H2NCH2C=O

H+ H+

C OO levulinate - OOC
H 2C H 2C

5-A mino-

b- u 1 0 c - s uc

s n it

G lyc ine +

3.5.3.1

3.5.3.6

CH 2 CH 2 N H

+ H 2 NC NHC H 2 C H 2 C H 2 C H (NH 3 ) C OO

NH 2

NO
1.14.13.39

A rgininos uc c inate

4-Hydroxyglutamate
HOC H HC N

1.5.1.12

C H2 C HC OO

TE

D P R OTONS

4.2.1.24

OOC

C H2 C H2 C OO -

A DP

Pi

H+ H+ H+ H+

A R G ININE
4.3.2.1
+ NH
2

HY DR OXY P R OL INE
HN C NH CO CH2 N C H3

3-Hydroxypyrroline5-c arboxylate

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

C OO -

4.1.1.37

Uroporphyrinogen

4.3.1.8 4.2.1.75

H2N

ATP
E ND
E R G O N IC R E

Y
A C T IO N

+ NH 2

+ NH 2

E lectron F low

P roton F low

H 2 NC NHC H 2 C OO

G uanidoac etate

2.1.1.2

H 2 NC N(C H 3 )C H 2 C OO

C reatine

2.7.3.2

P - HNC N(C H 3 )C H 2 C OO

1.5.1.2
S mall Numbers ( eg. 2.4.6.7) refer to the IUB MB E nzyme C ommis s ion (E C ) R eference Numbers of E nzymes

P -C reatine
3.5.2.10

P orphobilinogen

C reatinine

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