Statistical Inference for Networks

56

Transcript of Statistical Inference for Networks

Page 1: Statistical Inference for Networks
Page 2: Statistical Inference for Networks
Page 3: Statistical Inference for Networks
Page 4: Statistical Inference for Networks
Page 5: Statistical Inference for Networks
Page 6: Statistical Inference for Networks
Page 7: Statistical Inference for Networks

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

TR A NS 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

!2

1 "!

"

#

10 c-s ub-unitsAD P+ Pi

H+

3.6.1.34

H+ -transporting AT P synthase

"

$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-CH2CH2

H2NCH2C=O

F ADH2

F ADC yt.b

F e-S

S UC C INA T EII

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

1.2.4.12.3.1.123.1.3.43

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

IS OC IT R A T E

2.6.1.12.3.1.16

4.1.1.71

1.2.1.16

5.1.99.15.4.99.2

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 !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+

GlyceraldehydeRibulose-1,5-bis-P

2!

88

H +c

32

%

a

32

"1 "

%

"

!21

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+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-

Cyclic Photophosphorylation

PQ

PHOTO-SYSTEM II

Cyt bc

Non-cyclic electron flow2e-2e-

Mn2e-

*

Protons from Water

H2O

H+

H+

2H+

2H+

#

ATP synthase

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

A T P

A DP

A T P

1/2O2

H2O

PQH2

T o B rain -

AMI

NO

ACI

DS

PYRI

MI

DI

NES

PURI

NES

CATECHOLAMI

NES

AROMATI

C

AMI

NO

ACI

DS

hvV IS ION

LIPI

D

PHOTOSYNTHESIS

PORPHYRI

NS

STEROI

DS

ISOPRENOI

DS

PHOSPHOLIPI

DS

DEGRADATI

ON

LIPI

D

BI

OSYNTHESIS

PENTOSES

HEXOSES

POLYSACCHARI

DES

C O C H C H(NH )C OO2 3+

F OL ICA C ID

C 1P 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 OUPS 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 TO

OH

OH

O

OHAC 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

pyruvateN-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 HO

HOC H 2 C C C C C O

OH OHH OH

H HO

HOC H 2 C C C C O C O

OHH

H

OH H

C C

OH

C O

P -R ibos ylamine

G lyc erate2, 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 eUDP -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-Hydroxykynurenine

3-Hydroxyanthranilate

2-A mino-3-c arboxymuc 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

NH

C -C H(OH)C H(OH)C H O2 PC 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-5enolpyruvate 3-P

C horis mateP E P

2.7.1.71

1.4.1.19

Homogentis ate P henylpyruvate

C innamate

C oumarate

P rephenate

2-A minomuc onate

F umarate A s partate

G LY C INE

S arc os ine

Hydroxy-pyruvate

P -Hydroxy-pyruvate

S E R INE

Imidazoleglyc erol-P

P -R ibos yl-A T P P -R ibos ylformimino5-aminoimidazole-c arboxamide-R P

F ormiminoglutamate

Imidazolonepropionate

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 tidinal3.1.3.15 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 ulphinylpyruvate

Oxobutyrate

2-A c eto-2-hydroxy-butyrate

O-P hos pho-homos erine

HO S C H C H NH2 2 2 2

HypotaurineHO S C H C H NH3 2 2 2

T aurine

G lutamate

#-G lutamylc ys teine

G lutathione

G lyc ine

C ys teine

ß-A lanine

C ys teateS -A denos yl

homoc ys teine

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 -A denos ylmethionine

(S A M)

2-Methylac eto-ac etyl-C oA

2-A c etolac tate 2-3-Dihydroxyis ovalerate

2-Oxo-is ovalerate

3-Hydroxy-is obutyrate

3-Hydroxy-Is obutyryl-C oA

Methylac 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-methylvalerate

Is obutyryl-C oA

C ys teines 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

OHOHO

C OO

OHOH

HO P

C OO

OHOH

O

C H2

P

C OO

O-C -C OOOH

OOH

OOC C H C OC OO2

N H

HOC -C H(OH)C H(OH)C H 2OPC H

C OO

NH2

C OO

OHNH2C 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

#-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 IDA 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 holineG lyc erophos phoc holine

L ys olec ithin

C holineplas 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 oAA c yl-C oA

C erebros ideG 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)

"-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

OHOH

C HOHC H NHC H2 3

OHOH

C HOHC H NH2 2

4-OH-3-Methoxy-phenylglyc ol

C HOHC H NH2 2

OHOC H 3OC H 3

C HOHC H OH2

OH

OC H 3

4-OH-3-Methoxy-D-mandelate

C yc lic A MPA 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

OHOC H 3

C H(OH)C OO

H2

NH3

+C H-C OO

CO

O

C OO

NR ibose- PN+

C OO

NH

C H C OO2

O

OH

C H O2 P

NHC OC H NH2 2

OH

F ormylglyc inamide-R P

Urea

F ormylglyc 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 minoimidazole-R P

5-A mino-4-imidazolec arboxylate-R P

5-A mino-4-imidazole(N-s uc c inylc arboxamide)-R P

5-A minoimidazolec arboxamide-R P

F ormylamido-imidazole-

c arboxamide-R P

H NC ONH2 2

HNH C2 C HO

NHR P

NH

C

CCO

CC O

OCNH

N H

HN

HN

H

CCO

CC H

OCNH

N

N

HN

C arbamoylß-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-Ureidois obutyrate

Dihydrothymine

T hymine d-UMP d-C MP d-C DP

C DP

C arbamoylas partate

Dihydroorotate

Orotate Orotidine-P Uridine-P(UMP )

UDP

3-A mino-is obutyrate

C HCNH 2

C HOCNH

NC HCO

C HOCN H

HN

C H-C H3CO

OCN H

HN

C H 2

C H2C H2

CO

OCNH

HN

CO

C HOCN H

HN C C H3

Methylmalonyls emialdehyde

OHC C HC OO

C H3

C H2CO

C H-C OOOCN H

HN C HCO

C -C OOOCN H

HN

H NC ONHC H C H C OO2 2 2

CC

CC H

R PHC

NH

NH

OOC -C H-C H C OO2

N

N

N

C HO

NHR P

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 -C OOH

Oxalate

G lyc olate

HOC H C HO2

G lyc olaldehyde

E thanolamine-P

2.7.1.30

2.3.1.7

3.7.1.2

4.1.3.5

2.7.8.8

2.1.1.172.1.1.71

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

2.4.2.112.7.7.18

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

A C E T A T E

2.4.2.4

2.1.1.45

R P

C HCO

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

1.17.4.12.7.7.7

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 2P ropanoyl-C oA

1.1.1.31

2.1.3.14.1.1.415.1.99.1

6.4.1.3

6.3.2.5

2.1.1.14

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 etylneuraminate

C DP -diac ylglyc erol

C HOL INE

E thanolamine

G lyoxylate

HIS T A MINE

2.3.1.46Homos erine

T yramine

P lant P igmentsT annins

Maleylac etoac etate

F umarylac etoac etate

5.2.1.2

C H C OO2

OH

OH

OH

C H C H NH2 2 2

OHOH

C H C H NH2 2 2

Hydroxyphenylpyruvate

"-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

1.10.3.31.10.2.1

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

OHO

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 uanineDNA

6.3.4.44.3.2.2

CCO

CC H

HCNH

N

N

HN CCO

CC H

HCNH

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

2.7.4.62.7.4.32.7.4.4

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

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 ineH 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 minoadipates emialdehyde

2-A minoadipate2-Oxoadipate

A rginino-s uc c inate

G uanidoac etate

Methylmalonyl-C oA

4.1.2.12

A s partylS emialdehyde

2, 3-Dihydro-dipic olinate

1.2.1.114.2.1.52 1.3.1.26 P iperideine-

2, 6-dic arboxylateN-S uc c inyl-

2-amino-6-oxo-pimelate

2.6.1.17N-S uc c inyl-2, 6diaminopimelate

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 H3C 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 OOC 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

1.1.1.85Oxoleuc ine

C OOH

(C H ) C HC HC H(OH)C OO3 2

S -A denos ylmethylthiopropylamine

(Dec arboxylated S A M)

P R OL INE

C oenzyme A

C H C = C HC H3 2

C H 3

OC H

C H

3

3HO

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 phatidylethanolamine

C E P HA L IN

3.1.4.12

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 2.7.7.42.7.1.251.8.99.1A 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

2.1.1.102.1.1.20

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

G lyoxylate

2.1.1.6

1.4.3.41.14.18.1

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

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

S O -42

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

1.1.1.22

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

OP P U

C H OH2

C H OH2

HO OH

OH

HO

2.4.1.21

4.2.1.521.2.1.18

4.2.1.18

O

C HC

C HOCN

HN

DP

C HCO

C HOCN

HN

R P P P

OC H 2

H

C C

H

OHOH

C H

NHNCH

CP

H

O

OC H2 C C

H

OH

H

OH

C

H

C CC

NH2

CC H

HCN

R P (P P )

N

N

N+

P

NH2H

O

OC H 2 C C

H

OH

H

OH

C

H

C COC

CC H

HCN

R P

N

N

NHP

H

OC H 2 C C

H

OHOH

C O C H2 C

C ONH 2

CC H

HCN

R P

N

N

NHP

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

B etaine

B etainealdehyde

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

6.3.2.136.3.2.7-10

2.7.7.27

2.7.7.9

3.5.4.10

CCO

CC H

OCN R P

N

NH

HN

CCO

CC H

N

N

N

HN

R PH 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

NHNC

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 -

OC HOHC HOHAcNH

HO

OP C

OC O -C H OH2

OC HOHC HOHAcNH

HO

OH

C OOC H OH2

O

OHOH HOHO

C H O2 P

O

OHAC 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 PO

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 OH2O

OHO

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

OH

H 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 2C 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

OHOOH

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 oAC 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+

OHOH

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

C O

NH2

C H C H(NH )C OO2 3+

NHOC

C O

NHOC

NH

CH

H N2

HCC H

N

N

C

R PH N2

C HC

C HOCN

N

DP

NH2

R P P P

C HC

C HOCN

N

NH 2

CC

CC 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

NHNC

HC

H

C H C H(NH )C H OH2 3 2

+C

NHNC

HC

H

C H C H(NH )C H OP2 3 2C

NHNCH

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

CO

C -C OOOCN

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 H3CO

C HOCN 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 HC 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 C3N

H

NH

NH

NH

C H

C H

H C2

C

CH2

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

NH

-

-

C H2

H C2

H C2

H C2

H2

H2

C H2

C H2 C H2

C H2

C H2

C H2

NH

NH

NH

NH

C OO

C OO

C OOC 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

NH

NH

NH

NH

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 CNH 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 C2NH

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 2CH

OOC CN

HCC H-C OO

C H2CH2

C H-C OO OOC CN

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

+AdenosylS 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

NHNC

HC C H C HC OO2

NHC OC H C H NH2 2 2+

H

C

NHNC

HC C H C H(NH )C OO2 3

C HC H C H C OO2 2

NHNC H

O C C C H C HC OO

NHNC H

C H

C H C OO3

NH

OOC

C H-C OOOC

NH2 C H2

H NC H C H C OO2 2 2

H NC H2 2

C H3C HC OO H NC ONHC H C HC OO2 2

C H3

CCO

C H

R PHC N

N

N

HN

C

CCO

C HHC O

N

N

N R P

CC H

N

NH N2

HC

CCO

C H

N

NC

CC H

N

N

R P

H N2

H N2C

O

O

O P~ ~P O

O

O O

P O

O

C H2

N

N

N

N

O

OHOH

NH2

HCC HN

N

N

N O

O

P O O

O

C H2

OH

NH2

HCC H

C OOC O

NHOC

NH

CH

H N2NH2

OOC -C H-C H C OO2

HNC O CC H

N

N

C

R PR PH N2

OOCC

C H

NR P

N

CH N2

C H=C HC OO

OH

C H=C HC OO

C H C OC OO2

C H2

P

C OO

OHO

O

O

C OO

O

C H C OO2O

C H C OO2-OOC

OC H 2 C H2

OHHC

P

HOC H HC OH

OCC OO

C OOHO

OHOHO

NH2C OOOC H

NH

C H C OC OO2NH

C HO

C O

NH2OH

C H C H(NH )C OO2 3

+

N

C OO

C OO

N+

C OO

C OOR P

O

OH

OH

HO OP P U

C OO

O

OH

NHC OC H 3

HO

OP P U

C OOC H OH2

O

OCC H2 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 OOHO 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

NR ibose - O - P - O - P - O -Adenosine

O

O

O

O

II

IIOH

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

++

HOH

HOH

HHO

HHO

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-R23.1.1.32

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

NHNC

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-PDehydro-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 ylformimino5-aminoimidazole-c arboxamide-R P

Imidazoleac etol-P

HS HS O -

P A NTOT HE NA T E

3-Is opropyl-malate

S uc c inics emialdehyde

2.4.1.17

Diac ylglyc 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

2.4.1.1etc.

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

A DP

P -G luc onolac tone

1.1.1.44

O

OOHHO

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 ININEHY DR OXYP R OL INE

P HOS P HA T IDY LS 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

2.4.2.146.3.4.7

5.3.1.9

3.1.3.11

1.2.1.13

2.7.2.3

H

OH OH

C C C

H

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

2.7.1.362.7.4.2

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

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 erolF 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 INSG 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 O2O-

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 2C 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

Malonics emi-

aldehyde

2.7.2.4

2.1.3.3

3.5.1.26.3.1.2

6.3.5.5

C arbohydratesB iosynthes is

Degradation

A mino A c idsB iosynthes is

Degradation

L ipidsB iosynthes is

Degradation

P urines &P yrimidines

B iosynthes is

Degradation

B iosynthes is DegradationV 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 IONT 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 theMIT OC HONDR IAL INNE R ME MB R ANE

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

E lectron F low P roton F low

S mall Numbers ( eg. 2.4.6.7) refer to the IUB MB E nzymeC 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

TRANS L O C A T E D P R OTONS

2.7.1.1

A T P2.7.1.2

sigma-aldrich.com/pathw ays

A rgentinaSIGMA-ALDRICH DE ARGENTINA, S.A.Tel: 54 11 4556 1472Fax: 54 11 4552 1698

A ustraliaSIGMA-ALDRICH PTY., LIMITEDFree Tel: 1800 800 097 Free Fax: 1800 800 096Tel: 612 9841 0555Fax: 612 9841 0500

A ustriaSIGMA-ALDRICH HANDELS GmbHTel: 43 1 605 81 10Fax: 43 1 605 81 20

BelgiumSIGMA-ALDRICH NV/SA.Free Tel: 0800-14747Free Fax: 0800-14745Tel: 03 899 13 01Fax: 03 899 13 11

BrazilSIGMA-ALDRICH BRASIL LTDA.Tel: 55 11 3732-3100Fax: 55 11 3733-5151

CanadaSIGMA-ALDRICH CANADA LTD.Free Tel: 800-565-1400Free Fax: 800-265-3858Tel: 905-829-9500Fax: 905-829-9292

ChinaSIGMA-ALDRICH CHINA INC.Tel: 86-21-6386 2766Fax: 86-21-6386 3966

Czech RepublicSIGMA-ALDRICH s.r.o.Tel: 246 003 200Fax: 246 003 291

DenmarkSIGMA-ALDRICH DENMARK A/STel: 43 56 59 10Fax: 43 56 59 05

FinlandSIGMA-ALDRICH FINLANDTel: 358-9-350-92 50Fax: 358-9-350-92 555

FranceSIGMA-ALDRICH CHIMIE S.à.r.l.Tel appel gratuit: 0800 211 408Fax appel gratuit: 0800 031 052

GermanySIGMA-ALDRICH CHEMIE GmbHFree Tel: 0800-51 55 000Free Fax: 0800-649 00 00

GreeceSIGMA-ALDRICH (O.M.) LTDTel: 30 210 9948010Fax: 30 210 9943831

HungarySIGMA-ALDRICH KftTel: 06-1-235-9054Fax: 06-1-269-6470Ingyenes zöld telefon: 06-80-355-355Ingyenes zöld fax: 06-80-344-344

IndiaSIGMA-ALDRICH CHEMICALS PRIVATE LIMITEDTelephoneBangalore: 91-80-5112-7272Hyderabad:91-40-5531 5548 / 2784 2378Mumbai:91-22-2579 7588 / 2570 2364New Delhi:91-11-2616 5477 / 2619 5360FaxBangalore: 91-80-5112-7473Hyderabad: 91-40-5531 5466Mumbai: 91-22-2579 7589New Delhi: 91-11-2616 5611

IrelandSIGMA-ALDRICH IRELAND LTD.Free Tel: 1800 200 888Free Fax: 1800 600 222

IsraelSIGMA-ALDRICH ISRAEL LTD.Tel: 08-948-4100Fax: 08-948-4200

ItalySIGMA-ALDRICH S.r.l.Telefono: 02 33417310Fax: 02 38010737Numero Verde: 800-827018

JapanSIGMA-ALDRICH JAPAN K.K.Tokyo Tel: 03 5821 3111Tokyo Fax: 03 5821 3170

K oreaSIGMA-ALDRICH KOREATel: 031-329-9000Fax: 031-329-9090

M alaysiaSIGMA-ALDRICH (M) SDN. BHDTel: 603-56353321Fax: 603-56354116

M exicoSIGMA-ALDRICH QUÍMICA,S.A. de C.V.Free Tel: 01-800-007-5300Free Fax: 01-800-712-9920

The NetherlandsSIGMA-ALDRICH CHEMIE BVTel Gratis: 0800-0229088Fax Gratis: 0800-0229089Tel: 078-6205411Fax: 078-6205421

New ZealandSIGMA-ALDRICH PTY., LIMITEDFree Tel: 0800 936 666Free Fax: 0800 937 777

Norw aySIGMA-ALDRICH NORWAY ASTel: 23 17 60 60Fax: 23 17 60 50

PolandSIGMA-ALDRICH Sp. z o.o.Tel: (+61) 829 01 00Fax: (+61) 829 01 20

PortugalSIGMA-ALDRICH QUÍMICA, S.A.Free Tel: 800 20 21 80Free Fax: 800 20 21 78

RussiaSIGMA-ALDRICH RUSSIATechCare Systems, Inc.(SAF-LAB)Tel: 095-975-1917/3321Fax: 095-975-4792

SingaporeSIGMA-ALDRICH PTE. LTD.Tel: 65-6271 1089Fax: 65-6271 1571

South A fricaSIGMA-ALDRICH SOUTH AFRICA (PTY) LTD.Tel: 27 11 979 1188Fax: 27 11 979 1119

SpainSIGMA-ALDRICH QUÍMICA S.A.Free Tel: 900101376Free Fax: 900102028

Sw edenSIGMA-ALDRICH SWEDEN ABTel: 020-350510Fax: 020-352522Outside Sweden Tel: +46 8 7424200Outside Sweden Fax: +46 8 7424243

Sw itzerlandFLUKA CHEMIE GmbHSwiss Free Call: 0800 80 00 80Tel: +41 81 755 2828Fax: +41 81 755 2815

United K ingdomSIGMA-ALDRICH COMPANY LTD.Free Tel: 0800 717181Free Fax: 0800 378785Tel: 01747 833000Fax: 01747 833313

United StatesSIGMA-ALDRICHP.O. Box 14508St. Louis, Missouri 63178Toll-free: 800-325-3010Call Collect: 314-771-5750Toll-Free Fax: 800-325-5052Tel: 314-771-5765Fax: 314-771-5757Internet: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 ldrichProduct No. M 3907

XXX

Page 8: Statistical Inference for Networks
Page 9: Statistical Inference for Networks
Page 10: Statistical Inference for Networks
Page 11: Statistical Inference for Networks
Page 12: Statistical Inference for Networks
Page 13: Statistical Inference for Networks
Page 14: Statistical Inference for Networks
Page 15: Statistical Inference for Networks
Page 16: Statistical Inference for Networks
Page 17: Statistical Inference for Networks
Page 18: Statistical Inference for Networks
Page 19: Statistical Inference for Networks
Page 20: Statistical Inference for Networks
Page 21: Statistical Inference for Networks
Page 22: Statistical Inference for Networks
Page 23: Statistical Inference for Networks
Page 24: Statistical Inference for Networks
Page 25: Statistical Inference for Networks
Page 26: Statistical Inference for Networks
Page 27: Statistical Inference for Networks
Page 28: Statistical Inference for Networks
Page 29: Statistical Inference for Networks
Page 30: Statistical Inference for Networks
Page 31: Statistical Inference for Networks
Page 32: Statistical Inference for Networks
Page 33: Statistical Inference for Networks
Page 34: Statistical Inference for Networks
Page 35: Statistical Inference for Networks
Page 36: Statistical Inference for Networks
Page 37: Statistical Inference for Networks
Page 38: Statistical Inference for Networks
Page 39: Statistical Inference for Networks
Page 40: Statistical Inference for Networks
Page 41: Statistical Inference for Networks
Page 42: Statistical Inference for Networks
Page 43: Statistical Inference for Networks
Page 44: Statistical Inference for Networks
Page 45: Statistical Inference for Networks
Page 46: Statistical Inference for Networks
Page 47: Statistical Inference for Networks
Page 48: Statistical Inference for Networks
Page 49: Statistical Inference for Networks
Page 50: Statistical Inference for Networks
Page 51: Statistical Inference for Networks
Page 52: Statistical Inference for Networks
Page 53: Statistical Inference for Networks
Page 54: Statistical Inference for Networks
Page 55: Statistical Inference for Networks
Page 56: Statistical Inference for Networks