acetyl-CoA (PAMDB110382)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110382
Identification
Name: acetyl-CoA
Description:An acyl-CoA(4−) that is the tetraanion of acetyl-CoA, arising from deprotonation of the phosphate and diphosphate OH groups.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • acetyl coenzyme-A
  • ac-CoA
  • acetylcoenzyme-A
  • acetyl-S-CoA
  • ac-S-CoA
Chemical Formula: C23H34N7O17P3S
Average Molecular Weight: 805.54
Monoisotopic Molecular Weight: 809.1257730519
InChI Key: ZSLZBFCDCINBPY-ZSJPKINUSA-J
InChI: 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)/p-4/t13-,16-,17-,18+,22-/m1/s1
CAS number: 72-89-9
IUPAC Name:3'-phosphonatoadenosine 5'-(3-{(3R)-4-[(3-{[2-(acetylsulfanyl)ethyl]amino}-3-oxopropyl)amino]-3-hydroxy-2,2-dimethyl-4-oxobutyl} diphosphate)
Traditional IUPAC Name: acetyl-CoA
SMILES:CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(=O)(OP(=O)(OCC1(C(OP([O-])(=O)[O-])C(O)C(O1)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-]
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent Acyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Pentose phosphate
  • Ribonucleoside 3'-phosphate
  • Pentose-5-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • 6-aminopurine
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Imidolactam
  • N-acyl-amine
  • Fatty amide
  • Phosphoric acid ester
  • Alkyl phosphate
  • N-substituted imidazole
  • Pyrimidine
  • Heteroaromatic compound
  • Azole
  • Oxolane
  • Imidazole
  • Thiocarboxylic acid ester
  • Amino acid or derivatives
  • Carboxamide group
  • Carbothioic s-ester
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Organic oxide
  • Organic nitrogen compound
  • Primary amine
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Amine
  • Organic oxygen compound
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic anion
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
  • a CoA derivative (ACETYL-COA)
Physical Properties
State: Solid
Charge:-4
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.3 mg/mLALOGPS
logP-0.58ALOGPS
logP-7ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 Å2ChemAxon
Rotatable Bond Count20ChemAxon
Refractivity172.21 m3·mol-1ChemAxon
Polarizability71.4 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
3-oxopimeloyl-CoA + coenzyme A → glutaryl-CoA + acetyl-CoA
L-Glutamine + acetyl-CoA → N-acetylglutaminylglutamine + coenzyme A + Water + Hydrogen ion
3-amino-4-hydroxybenzaldehyde + acetyl-CoA → Hydrogen ion + 3-acetylamino-4-hydroxybenzaldehyde + coenzyme A
coenzyme A + acetate + ATP → phosphate + acetyl-CoA + ADP
ATP + acetyl-CoA + Water → malonyl-CoA + ADP + phosphate + Hydrogen ion
acetyl-CoA + Hydrogen ion → coenzyme A + Carbon dioxide
UDP-2-acetamido-3-amino-2,3-dideoxy-α-D-glucuronate + acetyl-CoA → UDP-2,3-diacetamido-2,3-dideoxy-α-D-glucuronate + coenzyme A + Hydrogen ion
succinyl-CoA + acetyl-CoA → 3-oxoadipyl-CoA + coenzyme A
OPC6-CoA + acetyl-CoA → OPC8-3-ketoacyl-CoA + coenzyme A
OPC4-CoA + acetyl-CoA → OPC6-3-ketoacyl-CoA + coenzyme A
5-methyl-3-oxo-4-hexenoyl-CoA + coenzyme A → 3-methylcrotonyl-CoA + acetyl-CoA
jasmonoyl-CoA + acetyl-CoA → OPC4-3-ketoacyl-CoA + coenzyme A
3-amino-4-hydroxybenzoate + acetyl-CoA → 3-acetylamino-4-hydroxybenzoate + coenzyme A
3-oxopropanoate + coenzyme A + NAD+ → acetyl-CoA + Carbon dioxide + NADH
4-hydroxybenzoyl-CoA + acetyl-CoA → 4-hydroxybenzoyl-acetyl-CoA + coenzyme A
butanoyl-CoA + acetyl-CoA → 3-oxohexanoyl-CoA + coenzyme A
2-methylacetoacetyl-CoA + coenzyme A → propanoyl-CoA + acetyl-CoA
3-oxo-23,24-bisnorchol-4-en-22-oyl-CoA + acetyl-CoA → 3,22-dioxochol-4-en-24-oyl-CoA + coenzyme A
Aryl-Amines + acetyl-CoA → N-acetylarylamines + coenzyme A
acetyl-CoA + propanoyl-CoA → β-ketovaleryl-CoA + coenzyme A
lauroyl-CoA + acetyl-CoA → 3-oxo-myristoyl-CoA + coenzyme-A-group
decanoyl-CoA + acetyl-CoA → 3-oxododecanoyl-CoA + coenzyme A
3-[(3aS,4S,5R,7aS)-5-hydroxy-7a-methyl-1-oxo-octahydro-1H-inden-4-yl]-3-oxopropanoyl-CoA + Water → 3-[(3aS,4S,5R,7aS)-5-hydroxy-7a-methyl-1-oxo-octahydro-1H-indene-4-carboxylate + acetyl-CoA
hexanoyl-CoA + acetyl-CoA → 3-oxooctanoyl-CoA + coenzyme A
acetyl-CoA + spermine → N1-acetylspermine + coenzyme A + Hydrogen ion
3-cis-dodecenoyl-CoA + acetyl-CoA → 3-keto-5-cis-tetradecenoyl-CoA + coenzyme A
6-cis, 3-oxo-tridecenoyl-CoA + coenzyme A → 4-cis-undecenoyl-CoA + acetyl-CoA
6-trans-3-oxo-tridecenoyl-CoA + coenzyme A → 4-trans-undecenoyl-CoA + acetyl-CoA
acetyl-CoA + spermidine → N1-acetylspermidine + Hydrogen ion + coenzyme A
4-trans-3-oxo-undecenoyl-CoA + coenzyme A → 2-trans-nonenoyl-CoA + acetyl-CoA
5-trans-3-oxo-dodecenoyl-CoA + coenzyme A → 3-trans-decenoyl-CoA + acetyl-CoA
5-cis, 7-trans-3-oxo-tetradecadienoyl-CoA + coenzyme A → 3-cis, 5-trans-dodecadienoyl-CoA + acetyl-CoA
L-Methionine + acetyl-CoA → N-α-acetyl-L-methionine + coenzyme A + Hydrogen ion
7-methyl-3-oxooct-6-enoyl-CoA + coenzyme A → 5-methylhex-4-enoyl-CoA + acetyl-CoA
ATP + acetyl-CoA + Hydrogen carbonate → Hydrogen ion + malonyl-CoA + phosphate + ADP
acetyl-CoA + putrescine → N-acetylputrescine + coenzyme A + Hydrogen ion
crotonate + acetyl-CoA → crotonyl-CoA + acetate
2,3-didehydroadipyl-CoA + acetyl-CoA → 3-oxo-5,6-didehydrosuberyl-CoA + coenzyme A
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1901000300-57c996f08055dba75dd7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0902000000-dffb00601bfc54014ae4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2901000000-155f0890adf4c76dca85View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0arr-6820231930-984ae0f98e0d17e4a7fcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3910100000-87da6b6d742efbc6e74aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900000000-8701decc3b2311880b97View in MoNA
References
References:
  • 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. [7857969 ]
  • 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. [947633 ]
  • 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. [16708048 ]
  • 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. [14681844 ]
  • 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. [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. [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. [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. [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. [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. [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. [6176686 ]
  • 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. [11701427 ]
  • Peters SJ: Regulation of PDH activity and isoform expression: diet and exercise. Biochem Soc Trans. 2003 Dec;31(Pt 6):1274-80. [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. [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. [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. [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. [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. [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. [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. [1885781 ]
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
External Links:
ResourceLink
CAS72-89-9
ChEBI57288
HMDBHMDB01206
IAF126033558
KEGGC00024
KNApSAcKC00007259
MetaboLightsMTBLC57288
PubChem45266541
UMBBD-Compoundsc0031