| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:10:06 -0700 |
| HMDB ID |
HMDB01206 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Acetyl-CoA |
| Description |
The main function of coenzyme A is to carry acyl groups (such as the acetyl group) or thioesters. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. (wikipedia). acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent. |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- Ac-CoA
- Ac-Coenzyme A
- Ac-S-CoA
- Ac-S-Coenzyme A
- Acetyl coenzyme-A
- Acetyl-CoA
- Acetyl-Coenzyme A
- Acetyl-S-CoA
- Acetyl-S-Coenzyme A
- Acetylcoenzyme-A
- S-Acetate CoA
- S-Acetate Coenzyme A
- S-Acetyl coenzyme A
|
| Chemical Formula |
C23H38N7O17P3S |
| Average Molecular Weight |
809.571 |
| Monoisotopic Molecular Weight |
809.125773051 |
| IUPAC Name |
{[(2R,3S,4R,5R)-2-({[({[(3R)-3-[(2-{[2-(acetylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-5-(6-amino-9H-purin-9-yl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid |
| Traditional IUPAC Name |
[(2R,3S,4R,5R)-2-[({[(3R)-3-[(2-{[2-(acetylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)methyl]-5-(6-aminopurin-9-yl)-4-hydroxyoxolan-3-yl]oxyphosphonic acid |
| CAS Registry Number |
72-89-9 |
| SMILES |
CC(=O)SCCNC(=O)CCNC(=O)[C@H](O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N |
| InChI Identifier |
InChI=1S/C23H38N7O17P3S/c1-12(31)51-7-6-25-14(32)4-5-26-21(35)18(34)23(2,3)9-44-50(41,42)47-49(39,40)43-8-13-17(46-48(36,37)38)16(33)22(45-13)30-11-29-15-19(24)27-10-28-20(15)30/h10-11,13,16-18,22,33-34H,4-9H2,1-3H3,(H,25,32)(H,26,35)(H,39,40)(H,41,42)(H2,24,27,28)(H2,36,37,38)/t13-,16-,17-,18+,22-/m1/s1 |
| InChI Key |
ZSLZBFCDCINBPY-ZSJPKINUSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Fatty Acid Esters |
| Sub Class |
Acyl CoAs |
| Other Descriptors |
- Aromatic Heteropolycyclic Compounds
- acyl-CoA(ChEBI)
|
| Substituents |
- 1 Phosphoribosyl Imidazole
- Aminopyrimidine
- Carboxamide Group
- Carboxylic Thioester
- Coenzyme A
- Glycosyl Compound
- Imidazole
- Imidazopyrimidine
- Monosaccharide Phosphate
- N Glycosyl Compound
- Organic Hypophosphite
- Organic Phosphite
- Organic Pyrophosphate
- Oxolane
- Pentose Monosaccharide
- Phosphoric Acid Ester
- Purine
- Purine Ribonucleoside 3',5' Bisphosphate
- Pyrimidine
- Saccharide
- Secondary Alcohol
- Secondary Carboxylic Acid Amide
- Thiocarboxylic Acid Ester
|
| Direct Parent |
Acyl CoAs |
| Ontology |
|---|
| Status |
Expected and Not Quantified |
| Origin |
|
| Biofunction |
- Cell signaling
- Component of Alanine and aspartate metabolism
- Component of Aminosugars metabolism
- Component of Arginine and proline metabolism
- Component of Bile acid biosynthesis
- Component of Butanoate metabolism
- Component of Fatty acid metabolism
- Component of Glutamate metabolism
- Component of Glycerophospholipid metabolism
- Component of Glycine, serine and threonine metabolism
- Component of Glyoxylate and dicarboxylate metabolism
- Component of Propanoate metabolism
- Component of Pyruvate metabolism
- Component of Tetracycline biosynthesis
- Component of Tryptophan metabolism
- Component of beta-Alanine metabolism
- Fuel and energy storage
- Fuel or energy source
- Membrane integrity/stability
|
| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
|
| Cellular locations |
- Cytoplasm
- Extracellular
- Membrane
- Mitochondria
- Nucleus
- Endoplasmic reticulum
- Golgi apparatus
- Peroxisome
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
Not Available
|
| Biological Properties |
|---|
| Cellular Locations |
- Cytoplasm
- Extracellular
- Membrane
- Mitochondria
- Nucleus
- Endoplasmic reticulum
- Golgi apparatus
- Peroxisome
|
| Biofluid Locations |
Not Available
|
| Tissue Location |
- Muscle
- Skeletal Muscle
- Brain
- Prostate
- Adipose Tissue
- Platelet
- Spleen
|
| Pathways |
|
| Normal Concentrations |
|---|
|
Not Available |
| Abnormal Concentrations |
|---|
|
Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB022491 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
392413  |
| KEGG Compound ID |
C00024 |
| BioCyc ID |
ACETYL-COA |
| BiGG ID |
33558 |
| Wikipedia Link |
Acetyl-CoA |
| NuGOwiki Link |
HMDB01206 |
| Metagene Link |
HMDB01206 |
| METLIN ID |
6082 |
| PubChem Compound |
444493 |
| PDB ID |
ACO |
| ChEBI ID |
15351 |
| References |
|---|
| Synthesis Reference |
Tucek, S. The synthesis of acetyl coenzyme A and acetylcholine from citrate and acetate in the nerve endings of mammalian brain. Biochimica et Biophysica Acta, General Subjects (1966), 117(1), 278-80. |
| Material Safety Data Sheet (MSDS) |
Not Available
|
| General References |
- Michno A, Skibowska A, Raszeja-Specht A, Cwikowska J, Szutowicz A: The role of adenosine triphosphate citrate lyase in the metabolism of acetyl coenzyme a and function of blood platelets in diabetes mellitus. Metabolism. 2004 Jan;53(1):66-72.
Pubmed: 14681844
- Al-Buheissi SZ, Patel HR, Meinl W, Hewer A, Bryan RL, Glatt H, Miller RA, Phillips DH: N-Acetyltransferase and sulfotransferase activity in human prostate: potential for carcinogen activation. Pharmacogenet Genomics. 2006 Jun;16(6):391-9.
Pubmed: 16708048
- Griffin MJ, Sul HS: Insulin regulation of fatty acid synthase gene transcription: roles of USF and SREBP-1c. IUBMB Life. 2004 Oct;56(10):595-600.
Pubmed: 15814457
- Putman CT, Spriet LL, Hultman E, Dyck DJ, Heigenhauser GJ: Skeletal muscle pyruvate dehydrogenase activity during acetate infusion in humans. Am J Physiol. 1995 May;268(5 Pt 1):E1007-17.
Pubmed: 7762627
- Szutowicz A, Tomaszewicz M, Jankowska A, Madziar B, Bielarczyk H: [Mechanisms of selective vulnerability of cholinergic neurons to neurotoxic stimuli] Postepy Hig Med Dosw. 1999;53(2):263-75.
Pubmed: 10355292
- Ingebretsen OC, Bakken AM, Farstad M: The content of coenzyme A, acetyl-CoA and long-chain acyl-CoA in human blood platelets. Clin Chim Acta. 1982 Dec 23;126(3):307-13.
Pubmed: 7151284
- Michno A, Raszeja-Specht A, Jankowska-Kulawy A, Pawelczyk T, Szutowicz A: Effect of L-carnitine on acetyl-CoA content and activity of blood platelets in healthy and diabetic persons. Clin Chem. 2005 Sep;51(9):1673-82. Epub 2005 Jul 14.
Pubmed: 16020499
- Constantin-Teodosiu D, Peirce NS, Fox J, Greenhaff PL: Muscle pyruvate availability can limit the flux, but not activation, of the pyruvate dehydrogenase complex during submaximal exercise in humans. J Physiol. 2004 Dec 1;561(Pt 2):647-55. Epub 2004 Oct 7.
Pubmed: 15579544
- Crystal HA, Davies P: Cortical substance P-like immunoreactivity in cases of Alzheimer's disease and senile dementia of the Alzheimer type. J Neurochem. 1982 Jun;38(6):1781-4.
Pubmed: 6176686
- Wysocki SJ, Wilkinson SP, Hahnel R, Wong CY, Panegyres PK: 3-Hydroxy-3-methylglutaric aciduria, combined with 3-methylglutaconic aciduria. Clin Chim Acta. 1976 Aug 2;70(3):399-406.
Pubmed: 947633
- Evans MK, Savasi I, Heigenhauser GJ, Spriet LL: Effects of acetate infusion and hyperoxia on muscle substrate phosphorylation after onset of moderate exercise. Am J Physiol Endocrinol Metab. 2001 Dec;281(6):E1144-50.
Pubmed: 11701427
- Peters SJ: Regulation of PDH activity and isoform expression: diet and exercise. Biochem Soc Trans. 2003 Dec;31(Pt 6):1274-80.
Pubmed: 14641042
- Roe CR, Sweetman L, Roe DS, David F, Brunengraber H: Treatment of cardiomyopathy and rhabdomyolysis in long-chain fat oxidation disorders using an anaplerotic odd-chain triglyceride. J Clin Invest. 2002 Jul;110(2):259-69.
Pubmed: 12122118
- Skibowska A, Raszeja-Specht A, Szutowicz A: Platelet function and acetyl-coenzyme A metabolism in type 1 diabetes mellitus. Clin Chem Lab Med. 2003 Sep;41(9):1136-43.
Pubmed: 14598862
- Girard J: [Contribution of free fatty acids to impairment of insulin secretion and action. mechanism of beta-cell lipotoxicity] Med Sci (Paris). 2005 Dec;21 Spec No:19-25.
Pubmed: 16598900
- Szutowicz A, Jankowska A, Tomaszewicz M: [Disturbances of glucose metabolism in epilepsy and other neurodegenerative diseases] Neurol Neurochir Pol. 2000;34 Suppl 8:59-66.
Pubmed: 11780590
- Spriet LL, MacLean DA, Dyck DJ, Hultman E, Cederblad G, Graham TE: Caffeine ingestion and muscle metabolism during prolonged exercise in humans. Am J Physiol. 1992 Jun;262(6 Pt 1):E891-8.
Pubmed: 1616022
- Constantin-Teodosiu D, Carlin JI, Cederblad G, Harris RC, Hultman E: Acetyl group accumulation and pyruvate dehydrogenase activity in human muscle during incremental exercise. Acta Physiol Scand. 1991 Dec;143(4):367-72.
Pubmed: 1815472
- Boden G, Jadali F, White J, Liang Y, Mozzoli M, Chen X, Coleman E, Smith C: Effects of fat on insulin-stimulated carbohydrate metabolism in normal men. J Clin Invest. 1991 Sep;88(3):960-6.
Pubmed: 1885781
- Blank ML, Smith ZL, Fitzgerald V, Snyder F: The CoA-independent transacylase in PAF biosynthesis: tissue distribution and molecular species selectivity. Biochim Biophys Acta. 1995 Feb 9;1254(3):295-301.
Pubmed: 7857969
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| Enzymes |
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| Name: |
ATP-citrate synthase
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| Reactions: |
- ADP + phosphate + acetyl-CoA + oxaloacetate = ATP + citrate + CoA [RN:R00352]
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| Gene Name: |
ACLY |
| Uniprot ID: |
P53396 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Fatty acid synthase
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| Reactions: |
- a (3R)-3-hydroxypalmitoyl-[acyl-carrier protein] = a hexadec-2-enoyl-[acyl-carrier protein] + H2O [RN:R04462]
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| Gene Name: |
FASN |
| Uniprot ID: |
P49327 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Peroxisomal acyl-coenzyme A oxidase 2
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| Reactions: |
- (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oyl-CoA + H2O + acceptor = (24R,25R)-3alpha,7alpha,12alpha,24-tetrahydroxy-5beta-cholestan-26- oyl-CoA + reduced acceptor [RN:R07374]
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| Gene Name: |
ACOX2 |
| Uniprot ID: |
Q99424 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
2-oxoisovalerate dehydrogenase subunit beta, mitochondrial
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| Reactions: |
- 3-methyl-2-oxobutanoate + [dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] lipoyllysine = [dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(2-methylpropanoyl)dihydrolipoyllysine + CO2 [RN:R01701]
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| Gene Name: |
BCKDHB |
| Uniprot ID: |
P21953 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial
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| Reactions: |
- 3-methyl-2-oxobutanoate + [dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] lipoyllysine = [dihydrolipoyllysine-residue (2-methylpropanoyl)transferase] S-(2-methylpropanoyl)dihydrolipoyllysine + CO2 [RN:R01701]
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| Gene Name: |
BCKDHA |
| Uniprot ID: |
P12694 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Acyl-CoA desaturase
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| Reactions: |
- stearoyl-CoA + 2 ferrocytochrome b5 + O2 + 2 H+ = oleoyl-CoA + 2 ferricytochrome b5 + 2 H2O [RN:R02222]
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| Gene Name: |
SCD |
| Uniprot ID: |
O00767 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Bile acyl-CoA synthetase
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| Reactions: |
- (1) ATP + cholate + CoA = AMP + diphosphate + choloyl-CoA [RN:R02794]
- (2) ATP + (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestan-26-oate + CoA = AMP + diphosphate + (25R)-3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoyl-CoA [RN:R04580]
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| Gene Name: |
SLC27A5 |
| Uniprot ID: |
Q9Y2P5 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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