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O

OH H
R SCoA N
O
H CH3 OH
Eicosanoid polyunsaturated acyl-CoA H +
O CH3
HO (HGLA or AA or EPA) O N H O NH3 O O O
cascades N
OH + +
CH CH2 NH3 HO CH CH2 CO 2H
CH3 LPA CH2
+ - PLP N + - - - H3N
+

Enoyl-CoA N NH3 O H threonine NH3 O phenylalanine O O tryptophan


H H
estradiol Phosphotidyl inositol isomerase histidine
aldosterone HO Cardiolipin histamine
O Phospholipase A2 4,5-bis-phosphate phenylpyruvate
O2
(- cortisol)
PLP ("phenyl ketone")
CDP-DAG ATP H2O
Histidine amonia Tetrahydrobiopterin
OH ATP lyase H2O Excreted in urine H
Phosphotidyl- SCoA N
H3C CH3 OH Phosphotidylserine Phosphotidyl-
glycerol Phosphotidyl- R
CH3 O CH3 O choline O O O Threonine dehydratase NAD(P)+
HO inositol Nh4+

Metabolic Map
CH3 O R1 O O R1 O R1 O OH O
OH OH Phospholipase A2 O Phenylalanine
CH3 CH3 Serine O O Lipase R2 O Nh4+ hydroxylase CO 2H OH
G-3-P HO R2 O R2 O O +
Inositol 1 B oxidation cycle and NAD(P)H H3N
testosterone Phosphotidyl- O P O R3 O P O R3 O R3 OH O 5-hydroxytryptophan
first oxidation of next cycle H O HO CH2 H
cortisol progesterone O
ethanolamine CDP-choline CDP-diacylglycerol O O monoacylglycerol N
H3C - phosphatide O
- triacylglycerol O H3C CH2
O O O
CH3 Dihydrobiopterin phenylacetate
lysophosphatide - O O
-
Acetyl-CoA N H O
Lecithin CH3 CH3 H 2-ketobuterate
(phosphotidyl choline) CDP-ethanolamine CTP urocanate H2O H
H3C N
Lecithin cholesterol O Diacylglycerol (DAG)
Pregnenolone O SCoA
acyl transferase (LCAT) R2 O +
cholesterol ester R NH3 O
H OH
R SCoA O I
O HO CH2 + +
Phosphotidase cis acyl-CoA NH3 H3N
serotonin
H3C - O H
R tyrosine O

Copyright 2005 Nathaniel Whitney Cholesteryl


esters
Acyl-CoA
acyltransferase
(ACAT) CH3
CH3

CH3
CH3
Bile acids
O O
O

R1
O
-

fatty acid Dienoyl-CoA


reductase
NADPH
HO

3-monoiodotyrosine (MIT)
CH2

O
-

R2 O O Enoyl-CoA isomerase
H
cholesterol (C27)
-
NADP+ OH N
HO O P O
CO 2H
- O O
phosphatidic acid O + O
Enoyl-CoA H3N CH2 OH
O O O H OH
isomerase
H3C H I NH
- R SCoA R SCoA + H3C N-acetylserotonin
CH3 O P O P O P O adenosine NH3 H
CH3 L-dopa O
Acyl transferase - - -
(onto C-2) O O O HO CH2
CH3 - B oxidation
CH3 O -
proceeds O
CH3 R as usual OH I 3,3'-diiodotyrosine (DIT)
HO lanosterol (C30) O H H
H3C CH3 N
Acyl transferase H3N
+
CH2 OH
Sphingomyelin Cerebrosides (onto C-1)
Cyclase Acetyl-CoA H O
Fatty acyl-CoA synthase H OCH3
DAG dopamine I I
O O H3C NH
OH + melatonin
NH3 H
NADH + H2O - - O
Squalene UDP-sugars HO O O P O P O
monoxygenase HO O CH2
- -
Phosphotidyl- - O O
NADPH + O2 O P O OH O
-
choline Fatty acyl-CoA glycerol O
- H OH
3-phosphate O CoA SH O OH I
Squalene O P O adenosine +
Oligosaccharide H3N OH 3,5,3'-triiodothyronine (T3)
O HO CH CH (CH2)12 CH3 O O CH2 CH2 R1 CH2 CH3
containing HO (CH2)14 CH3 2 Pi Ppi + AMP NAD+ R -
ADP O - H H
4Pi 2Ppi N-acetylneura- R NH + H3C O O O
H3N Acetyl-CoA O fatty acyl-adenylate Pi D-B-hydroxybutyrate
minic acid Acyl-CoA synthase RCOO- O2 + NADPH norepinephrine
Ganglioside OH Acyl-CoA Serine Glycerol 3-phosphate O P O choline
OH (enzyme bound)
Squalene synthase ceramide dehydrogenase platelet-activating -
NADH Glycerol O
sphinganine (Adipose) AdoMet
ATP kinase factor (PAF) O Cyto P-450-2E1 I I
OH
Fernesylated Fernesyl pyrophosphate (Liver) CYP2E1 +
D-3-hydroxybutyrate Phenylethanolamine NH3
proteins NADPH CoA-SH H3C (SER) H2O + NADP+ O
Fatty acyl-CoA synthase H3C CH3 Acetoacetate dehydrogenase NAD+ N-methyltransferase
O ATP NADH H
1-alkyl 2-acyl decarboxylase HO O CH2
Fatty acid Plasmologen acetone ethanol
O
-
P O
-
phosphotidylcholine AdoHcy -
O O O O
O Alcohol HO
H3C Dihydroxyacetone
O dehydrogenase I I
Glycerol phosphate CH2 CH3 H3C CH2 H3C OH OH
OH O (cytosol)
O P O O - H OH
H3C CH3 CH3 O acetoacetate H 3,5,3',5'-tetraiodothyronine
- acetoacetyl-CoA SCoA O
Geramylgeramyl O Dehydration H2O + ADP H3C NH OH
O fernesyl pyrophosphate H3C S (thyroxine [T4])
R SCoA H3C
- pyrophosphate NADH CYP2E1
O P O NADPH ACP acyl-CoA Acetyl-CoA Succinate H H H
-
O O O
SH CoASH acetaldehyde epinephrine
FMN FAD HMG-CoA lyase Succinyl-CoA
OH Longer saturated H2O + NAD+
KS
2Pi Ppi H3C S fatty acids Alhehyde
HO OH
Dolichol Coenzyme Q

Purine synthesis
Prenyl transferase Acyl-CoA dehydrogenase
NADP+ Reduction ACP O (mitochondria)
dehydrogenase
FMNH2 SH
(CH2)n O OH O
Ribose phosphate Elongation FADH2 NADH + H+
Geramylgeramylated H3C (CH2)m O
-
phosphofructokinase KS CH2 CH2
proteins O
Desaturation -
monounsaturated fatty acyl-CoA O SCoA
O O O CH3 H3C
glutamine Stearate 18:0 [Palmitoleate 16:1 (9), oleate 18:1 (9)]
O
- - OH
- O P O O FMNH2 NADP+ B-hydroxy-B-methylglutarul-CoA acetate
H2N O O
O
H3C SCoA
- NH2 O R (HMG-CoA)
O P
-
O
Reduction 2Cyt b5 trans enoyl-CoA Leucine
O H3C S
O O O
CH3 CH3 O P O (Fe3+) Cyt b5 reductase Lysine
Fatty acid synthase (FADH2) NADP+ H2O Acetate-CoA
O P O P O
-
ACP NADPH Fatty acyl-CoA CoASH
- - geranyl pyrophosphate
O
-
FMN Phenylalanine Mg++ ligase
O O
spiral continues until Elongation desaturase
HO OH
SH Enoyl-CoA Tryptophan HMG synthase
palmitoyl-S-ACP is formed
5'-phosphoribosyl 1-pyrophosphate (PRPP) hydratase Tyrosine O O O
KS KS = b-ketoacyl-ACP synthase O O
Ppi O Acetyl-CoA - -
2Pi ACP = acyl carrier protein
O P O P O + H3C
(CH2)n 2 Cyt b5
Prenyl transferase - Cyt b5 reductase O
O P O adenosine
H3C (CH2)m O NADPH + H+ O - -
H3C S
(Fe2+) (FAD) O
O O
-
OH O
Co2 saturated fatty acyl-CoA H3C CH2 inorganic pyrophosphate
glycine
acetyl adenylate
Branched-chain amino acid catabolism
H2N ACP
[Palmitate 16:0] SCoA
SH R SCoA acetoacetyl-CoA (PPi)
O O H CoASH
- H2O ACP-SH
O P O HO O Condensation KS L-B-hydroxyacyl-CoA CoASH
- NH2
O + PPi O Acetate-CoA
O
O
-
P O
- NAD+
CH3 ligase -
+ glutamate - - - O O
CH3
O P O O O
H3C CH O
HO OH Translocation B-hydroxyacyl-CoA dehydrogenase Thiolase O O
-
H2C CH2 O +
+
O P O O O Acetyl-CoA H3N H3N
5'-phosphoribosyl amine dimethyl Allyl O
O P O - NADH +
isopentenyl pyrophosphate (DMAP) O H3C H3N CH2 H3C
- - SH
O O S SCoA
pyrophosphate (IPP) O O O H3C H3C CH2
O ACP O
O ACP
CH3 CH3 CH3
NH3 + CO2 + ATP -
Pyrimadine synthesis

Pi O S-CoA
S R SCoA valine
H2N H3C
B-ketoacyl-CoA leucine isoleucine
O H3C S
O
- O malonyl-CoA
carbamoyl NH2 O P O KS
O O Co2 KS
phosphate O
- NH
NH O
- CH2 R3 H CoASH
O O P O O O Branched-chain Branched-chain
N
Pyrophosphomevalonate Acyl-CoA Branched-chain
- O H N aminotransferase aminotransferase
O R1 N O -
decarboxylate acetyltransferase aminotransferase
H3N
+
N H - O HO OH
O H
N
O
SCoA
(thiolase)
5'-phosphoribosylglycinamide (Glucagon) R
O
-
(epinephrine)
Acetyl-CoA
O ACC-P acyl-CoA O O
- -
R2 N H
H2N N N carboxylase (ACC) O O
-
O
-
H N10-formyl tetrahydrofolate (inactive) O O
aspartic acid H
O complex
H
- - (- palmitoyl-CoA) O O
O P O
5,10-methylene-THF O CH3 Transcarboxylase O
O O H3C CH2
glutamine O
CH2 CH2 O
H3C
- - CH3 H3C
O NH2 O O O P O
Biotin Biotin-CO2 CH2
H2N - - H3C S-CoA CH3
Loading 1 carbon O P O O
O CoASH CH3
(1 carbon pool) O NH - ATP + acetyl-CoA CoASH
- OH O ADP + Pi CoASH
NH2 O O
-
O
HCO3- Biotin carboxylase Branched-chain
O P O H
- a-keto acid NAD+ Branched-chain
NH R3 O O NH ADP dehydrogenase
O H
N HMG-CoA reductase - P a-keto acid NAD+ Branched-chain
NH2 O complex
R1 N
H dehydrogenase a-keto acid
-
H2O complex NAD+
O O O
HO OH
Pyrophosphomevalonate Co2 dehydrogenase
H NH
decarboxylate Co2
carbamoyl aspartate (LDL) Cholesterol Glucagon Co2 complex
O 5'-phosphoribosyl
O
-
H Insulin Acetyl-CoA
R2 N O H NH N-formylglycinamide
ADP Adenylate
O - O SCoA
glycine H H
N H
O
- O ATP cyclase Thiolase
N Pi CAMP
H2O PKA O SCoA
10-hydroxymethyl-THF H3C O SCoA
H2N N N H tetrahydrofolate
O
CoA-SH
H O ADP ATP ATP CH3 CH2
NH CoA-SH
O
O
-
P O
-
O CH3 ADP ATP Acetyl-CoA H3C
O OH O CH3
O
-
P O H - H3C
H O CH2 CH2 O O CH3 OH O OH O O CH2
- NH CH2 CH2 O
H
O O NH HMG-CoA reductase CH3
HN -
serine NH2 Reduction H O
-
OH O P O Phosphomevalonate O OH O P O CH2 CH2 CH2 CH2 H3C CH2