Record Information
Version 1.0
Update Date 1/22/2018 12:54:53 PM
Metabolite IDPAMDB000298
Identification
Name: Acetyl-CoA
Description:Acetyl-CoA is the thioester formed between coenzyme A (a thiol) and acetic acid (an acyl group carrier). Acetyl-CoA is produced during the second step of aerobic cellular respiration, pyruvate decarboxylation. Its main function is to convey the carbon atoms within the acetyl group to the citric acid cycle (Krebs cycle) to be oxidized for energy production.
Structure
Thumb
Synonyms:
  • Ac-S-CoA
  • Ac-CoA
  • Ac-Coenzyme A
  • Ac-S-CoA
  • Ac-S-Coenzyme A
  • AcCoA
  • Acetyl coenzyme A
  • Acetyl coenzyme-A
  • Acetyl-S-CoA
  • Acetyl-CoA
  • Acetyl-Coenzyme A
  • Acetyl-S-CoA
  • Acetyl-S-Coenzyme A
  • Acetylcoenzyme A
  • Acetylcoenzyme-A
  • S-Acetate CoA
  • S-Acetate Coenzyme A
  • S-Acetic acid CoA
  • S-Acetic acid Coenzyme A
  • S-Acetyl coenzyme A
Chemical Formula: C23H38N7O17P3S
Average Molecular Weight: 809.571
Monoisotopic Molecular Weight: 809.125773051
InChI Key: ZSLZBFCDCINBPY-ZSJPKINUSA-N
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)/t13-,16-,17-,18+,22-/m1/s1
CAS number: 72-89-9
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: acetyl-CoA
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
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 diphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Beta amino acid or derivatives
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • N-acyl-amine
  • Monosaccharide
  • Fatty amide
  • Saccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Thiocarboxylic acid ester
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Sulfenyl compound
  • Thioether
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-4
Melting point: Not Available
Experimental Properties:
PropertyValueSource
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: Cytoplasm
Reactions:
Coenzyme A + 2 flavodoxin semi oxidized + Pyruvic acid <> Acetyl-CoA + Carbon dioxide +2 Flavodoxin reduced + Hydrogen ion
Coenzyme A + Pyruvic acid <> Acetyl-CoA + Formic acid
Coenzyme A + NAD + Pyruvic acid > Acetyl-CoA + Carbon dioxide + NADH
Acetyl-CoA + Adenosine triphosphate + Hydrogen carbonate <> ADP + Hydrogen ion + Malonyl-CoA + Phosphate
Acetaldehyde + Coenzyme A + NAD <> Acetyl-CoA + Hydrogen ion + NADH
acyl carrier protein + Acetyl-CoA <> Acetyl-ACP + Coenzyme A
3-Oxo-5,6-dehydrosuberyl-CoA + Coenzyme A <> 5-Carboxy-2-pentenoyl-CoA + Acetyl-CoA
Acetoacetic acid + Acetyl-CoA > Acetoacetyl-CoA + Acetic acid
Acetyl-CoA + Butyric acid > Acetic acid + Butyryl-CoA
Acetyl-CoA + Hexanoate (N-C6:0) > Acetic acid + Hexanoyl-CoA
2 Acetyl-CoA <> Acetoacetyl-CoA + Coenzyme A
Acetyl-CoA + Phosphate <> Acetylphosphate + Coenzyme A
Acetyl-CoA + Octanoyl-CoA <> 3-Oxodecanoyl-CoA + Coenzyme A
Acetyl-CoA + Butyryl-CoA <> 3-Oxohexanoyl-CoA + Coenzyme A
Acetyl-CoA + Tetradecanoyl-CoA <> 3-Oxohexadecanoyl-CoA + Coenzyme A
Acetyl-CoA + Hexanoyl-CoA <> 3-Oxooctanoyl-CoA + Coenzyme A
Acetyl-CoA + Lauroyl-CoA <> 3-Oxotetradecanoyl-CoA + Coenzyme A
Acetyl-CoA + Decanoyl-CoA (N-C10:0CoA) <> 3-Oxododecanoyl-CoA + Coenzyme A
3-Oxooctadecanoyl-CoA + Coenzyme A <> Acetyl-CoA + Palmityl-CoA
Acetyl-CoA + Glyoxylic acid + Water <> Coenzyme A + Hydrogen ion + L-Malic acid
alpha-Ketoisovaleric acid + Acetyl-CoA + Water + a-Ketoisovaleric acid <> 2-Isopropylmalic acid + Coenzyme A + Hydrogen ion
Acetyl-CoA + D-Glucose <> 6-Acetyl-D-glucose + Coenzyme A
Acetyl-CoA + D-Maltose <> Acetyl-maltose + Coenzyme A
Acetyl-CoA + Water + Oxalacetic acid <> Citric acid + Coenzyme A + Hydrogen ion
Acetyl-CoA + Hydrogen ion + Malonyl-[acyl-carrier protein] > Acetoacetyl-ACP + Carbon dioxide + Coenzyme A
Coenzyme A + 3-Oxoadipyl-CoA <> Acetyl-CoA + Succinyl-CoA
Acetyl-CoA + 2-Aminobenzoic acid > N-Acetylanthranilate + Coenzyme A
Acetyl-CoA + Spermidine > N1-Acetylspermidine + Coenzyme A + Hydrogen ion
Acetyl-CoA + Spermidine > Coenzyme A + Hydrogen ion + N8-Acetylspermidine
Acetyl-CoA + Rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate > O-Acetyl-rhamanosyl-N-acetylglucosamyl-undecaprenyl diphosphate + Coenzyme A
Acetyl-CoA + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acid
Acetyl-CoA + L-Serine <> O-Acetylserine + Coenzyme A
Acetyl-CoA + Glycine <> L-2-Amino-3-oxobutanoic acid + Coenzyme A
Acetyl-CoA + N-Acetyl-glucosamine 1-phosphate > N-Acetyl-glucosamine 1-phosphate + Coenzyme A + Hydrogen ion
Acetyl-CoA + dTDP-D-Fucosamine > Coenzyme A + dTDP-4-Acetamido-4,6-dideoxy-D-galactose + Hydrogen ion
Acetic acid + Adenosine triphosphate + Coenzyme A <> Acetyl-CoA + Adenosine monophosphate + Pyrophosphate
Acetyl-CoA + L-Glutamate <> Coenzyme A + N-Acetyl-L-alanine
Citric acid + Coenzyme A <> Acetyl-CoA + Water + Oxalacetic acid
L-Malic acid + Coenzyme A <> Acetyl-CoA + Water + Glyoxylic acid
Adenosine triphosphate + Acetyl-CoA + Hydrogen carbonate <> ADP + Phosphate + Malonyl-CoA
Propionyl-CoA + Acetyl-CoA <> Coenzyme A + 2-Methylacetoacetyl-CoA
Acetyl-CoA + Putrescine <> Coenzyme A + N-Acetylputrescine
Acetyl-CoA + Butanoyl-CoA <> Coenzyme A + 3-Oxohexanoyl-CoA
Butanoyl-CoA + Acetic acid <> Butyric acid + Acetyl-CoA
2 Reduced ferredoxin + Acetyl-CoA + Carbon dioxide + 2 Hydrogen ion + Oxidized ferredoxin <>2 Oxidized ferredoxin + Pyruvic acid + Coenzyme A + Reduced ferredoxin
2-Isopropylmalic acid + Coenzyme A <> Acetyl-CoA + alpha-Ketoisovaleric acid + Water
Acetyl-CoA + Acyl-carrier protein <> Coenzyme A + Acetyl-[acyl-carrier protein]
Acetyl-CoA + Enzyme N6-(dihydrolipoyl)lysine + Enzyme N6-(dihydrolipoyl)lysine <> Coenzyme A + [Dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine
Acetyl-CoA + Carboxybiotin-carboxyl-carrier protein <> Malonyl-CoA + Holo-[carboxylase]
Acetyl-CoA + alpha-D-Glucosamine 1-phosphate <> Coenzyme A + Glucosamine-1P
3-Hydroxy-5-oxohexanoate + Acetyl-CoA <> 3-Hydroxy-5-oxohexanoyl-CoA + Acetic acid
7-Methyl-3-oxo-6-octenoyl-CoA + Coenzyme A <> 5-Methylhex-4-enoyl-CoA + Acetyl-CoA
5-Methyl-3-oxo-4-hexenoyl-CoA + Coenzyme A <> 3-Methylcrotonyl-CoA + Acetyl-CoA
Demethylphosphinothricin + Acetyl-CoA <> N-Acetyldemethylphosphinothricin + Coenzyme A
L-Methionine + Acetyl-CoA N-&alpha;-acetyl-L-methionine + Coenzyme A
alpha-Ketoisovaleric acid + Acetyl-CoA + Water > Hydrogen ion + 3-Carboxy-3-hydroxy-isocaproate + Coenzyme A
an <i>N</i>-hydroxy-arylamine + Acetyl-CoA <> an <i>N</i>-acetoxyarylamine + Coenzyme A
Glucosamine-1P + Acetyl-CoA > Hydrogen ion + <i>N</i>-acetyl-&alpha;-D-glucosamine 1-phosphate + Coenzyme A
a 2,3,4-saturated fatty acyl CoA + Acetic acid <> a fatty acid + Acetyl-CoA
Glycine + Acetyl-CoA <> Hydrogen ion + L-2-Amino-3-oxobutanoic acid + Coenzyme A
an aliphatic &alpha;,&omega;-diamine + Acetyl-CoA <> an aliphatic <i>N</i>-acetyl-diamine + Coenzyme A + Hydrogen ion
Acetyl-CoA + Dihydrolipoamide Coenzyme A + S-Acetyldihydrolipoamide
a &beta;-D-galactoside + Acetyl-CoA <> a 6-acetyl-&beta;-D-galactoside + Coenzyme A
a 2,3,4-saturated fatty acyl CoA + Acetyl-CoA < a 3-oxoacyl-CoA + Coenzyme A
L-Glutamate + Acetyl-CoA <> Hydrogen ion + <i>N</i>-acetyl-L-glutamate + Coenzyme A
3-Oxo-5,6-dehydrosuberyl-CoA + Coenzyme A > 2,3-dehydroadipyl-CoA + Acetyl-CoA
Adenosine triphosphate + Acetyl-CoA + Carbonic acid > ADP + Inorganic phosphate + Malonyl-CoA
Acyl-CoA + Acetic acid > a fatty acid anion + Acetyl-CoA
Acetyl-CoA + Citric acid > Acetic acid + (3S)-Citryl-CoA
(3S)-Citryl-CoA > Acetyl-CoA + Oxalacetic acid
Acetyl-CoA + Ribosomal-protein L-alanine <> Coenzyme A + Ribosomal-protein N-acetyl-L-alanine
Acetyl-CoA + N-Hydroxyarylamine <> Coenzyme A + N-Acetoxyarylamine
Acetyl-CoA + Alkane-alpha,omega-diamine <> Coenzyme A + N-Acetyldiamine
Acyl-CoA + Acetic acid <> Fatty acid anion + Acetyl-CoA
Acetyl-CoA + dTDP-D-Fucosamine <> Coenzyme A + dTDP-4-acetamido-4,6-dideoxy-alpha-D-galactose
Acetyl-CoA + beta-D-Galactoside <> Coenzyme A + 6-Acetyl-beta-D-galactoside
Acetyl-CoA + Oxalic acid <> Acetic acid + Oxalyl-CoA
Acyl-CoA + Acetyl-CoA <> Coenzyme A + 3-Oxoacyl-CoA
Acetyl-CoA + Malonyl-[acyl-carrier protein] <> Acetoacetyl-[acp] + Coenzyme A + Carbon dioxide
Acetyl-CoA + 3-Hydroxy-5-oxohexanoate > Acetic acid + 3-Hydroxy-5-oxohexanoyl-CoA + 3-Hydroxy-5-oxohexanoyl-CoA
a 3-oxoacyl-CoA? + Coenzyme A > Acetyl-CoA + a 2,3,4-saturated fatty acyl CoA?
Acetoacetyl-CoA + Coenzyme A + Acetoacetyl-CoA > Acetyl-CoA + Succinyl-CoA + Succinyl-CoA
3-Oxodecanoyl-CoA + Coenzyme A > Acetyl-CoA + Lauroyl-CoA
3-Oxohexanoyl-CoA + Coenzyme A > Acetyl-CoA + Octanoyl-CoA + Octanoyl-CoA
3-Oxododecanoyl-CoA + Coenzyme A > Acetyl-CoA + Tetradecanoyl-CoA
3-Oxotetradecanoyl-CoA + Coenzyme A > Acetyl-CoA + Palmityl-CoA
3-Oxooctanoyl-CoA + Coenzyme A > Acetyl-CoA + Decanoyl-CoA (n-C10:0CoA) + Decanoyl-CoA (N-C10:0CoA)
3-Oxohexadecanoyl-CoA + Coenzyme A > Acetyl-CoA + Stearoyl-CoA + Stearoyl-CoA
3-Oxooctadecanoyl-CoA + Coenzyme A + 3-Oxooctadecanoyl-CoA > Acetyl-CoA + Stearoyl-CoA + Stearoyl-CoA
Coenzyme A + 7-Methyl-3-oxo-6-octenoyl-CoA > Acetyl-CoA + 5-Methylhex-4-enoyl-CoA
Coenzyme A + 5-Methyl-3-oxo-4-hexenoyl-CoA > Acetyl-CoA + 3-Methylcrotonyl-CoA
2 Acetyl-CoA <> Acetoacetyl-CoA + Coenzyme A + Acetoacetyl-CoA
L-Glutamic acid + Acetyl-CoA + L-Glutamate > Coenzyme A + Hydrogen ion + N-Acetylglutamic acid + N-Acetylglutamic acid
Decanoyl-CoA (n-C10:0CoA) + Acetyl-CoA + Decanoyl-CoA (N-C10:0CoA) > 3-Oxododecanoyl-CoA + Coenzyme A
Octanoyl-CoA + Acetyl-CoA + Octanoyl-CoA <> 3-Oxodecanoyl-CoA + Coenzyme A
Acetyl-CoA + Hexanyl-CoA <> 3-Oxooctanoyl-CoA + Coenzyme A
Acetyl-CoA + Butyryl-CoA + Butyryl-CoA > 3-Oxohexanoyl-CoA + Coenzyme A
Acetyl-CoA + Hydrogen carbonate + Adenosine triphosphate > Adenosine diphosphate + Phosphate + Hydrogen ion + Malonyl-CoA + ADP + Malonyl-CoA
a malonyl-[acp] + Hydrogen ion + Acetyl-CoA > Carbon dioxide + Coenzyme A + acetoacetyl-[acp]
Acetyl-CoA + a holo-[acyl-carrier protein] > Coenzyme A + an acetyl-[acp]
L-Serine + Acetyl-CoA + L-Serine > Coenzyme A + O-Acetylserine
3-Methyl-2-oxovaleric acid + Water + Acetyl-CoA + 3-Methyl-2-oxovaleric acid > Coenzyme A + Hydrogen ion + 2-Isopropylmalic acid
Glyoxylic acid + Water + Acetyl-CoA > Coenzyme A + Hydrogen ion + L-Malic acid + L-Malic acid
3-hydroxy-2,4-pentanedione 5-phosphate + Coenzyme A + 3-hydroxy-2,4-pentanedione 5-phosphate > Acetyl-CoA + Dihydroxyacetone phosphate
Glucosamine-1P + Acetyl-CoA + Glucosamine-1P > N-Acetyl-glucosamine 1-phosphate + Coenzyme A + Hydrogen ion + N-Acetyl-glucosamine 1-phosphate
Acetyl-CoA + dTDP-thomosamine > TDP-Fuc4NAc + Coenzyme A + Hydrogen ion
Acetyl-CoA + L-Glutamic acid + L-Glutamate <> N-Acetyl-L-alanine + Coenzyme A + Hydrogen ion + N-Acetylglutamic acid + N-Acetyl-L-alanine + N-Acetylglutamic acid
Acetyl-CoA + Dihydrolipoamide + Dihydrolipoamide <> Coenzyme A + S-Acetyldihydrolipoamide
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:
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  • 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
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  • 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
  • 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
  • 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
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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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
CHEBI ID15351
HMDB IDHMDB01206
Pubchem Compound ID6302
Kegg IDC00024
ChemSpider ID392413
WikipediaAcetyl-CoA
BioCyc IDACETYL-COA
EcoCyc IDACETYL-COA
Ligand ExpoACO