Acetyl-CoA (CHEM035121)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:30:23 UTC
Update Date2016-11-09 01:21:15 UTC
Accession NumberCHEM035121
Identification
Common NameAcetyl-CoA
ClassSmall Molecule
Description
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
AcCoAChEBI
Acetyl coenzyme AChEBI
S-Acetyl-CoAChEBI
S-Acetyl-coenzyme AChEBI
Ac-CoAHMDB
Ac-coenzyme AHMDB
Ac-S-CoAHMDB
Ac-S-coenzyme AHMDB
Acetyl-coenzyme AHMDB
Acetyl-S-CoAHMDB
Acetyl-S-coenzyme AHMDB
Acetylcoenzyme AHMDB
S-Acetate CoAHMDB
S-Acetate coenzyme AHMDB
S-Acetyl coenzyme AHMDB
coenzyme A, AcetylHMDB
Acetyl CoAHMDB
CoA, AcetylHMDB
Chemical FormulaC23H38N7O17P3S
Average Molecular Mass809.571 g/mol
Monoisotopic Mass809.126 g/mol
CAS Registry Number72-89-9
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 Nameacetyl-CoA
SMILESCC(=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 IdentifierInChI=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 KeyZSLZBFCDCINBPY-ZSJPKINUSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as o-glucuronides. These are glucuronides in which the aglycone is linked to the carbohydrate unit through an O-glycosidic bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glucuronides
Alternative Parents
Substituents
  • 1-o-glucuronide
  • O-glucuronide
  • Glycosyl compound
  • O-glycosyl compound
  • Pyrrolidinylpyridine
  • Alkaloid or derivatives
  • Beta-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Oxane
  • Pyran
  • Pyridine
  • Pyrrolidone
  • 2-pyrrolidone
  • N-alkylpyrrolidine
  • Pyrrolidine
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxamide group
  • Lactam
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid
  • Oxacycle
  • Carboxylic acid derivative
  • Polyol
  • Acetal
  • Monocarboxylic acid or derivatives
  • Organopnictogen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility4.3 g/LALOGPS
logP-0.58ALOGPS
logP-5.9ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity172.21 m³·mol⁻¹ChemAxon
Polarizability70.62 ųChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 35V, positivesplash10-0fb9-0035910000-cecfaf54528fc3ef9f00Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 35V, positivesplash10-0ufr-0005900000-491971eb7a5c2b327554Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 35V, negativesplash10-0a4i-0900000000-1b259612c3897ed851f0Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 35V, negativesplash10-08i0-0001901200-8d4f5232c27f2875cf8bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT 35V, negativesplash10-08i0-0000901200-33f8d3ced8c83336df0cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 33V, Negativesplash10-0a4i-1101800090-5031dc04edf8ba0f3afbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 33V, Negativesplash10-0a4i-1101900080-6691464da5a030f7d086Spectrum
LC-MS/MSLC-MS/MS Spectrum - 33V, Negativesplash10-0a4i-1101900080-8a1491c56fc1331c5df1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 33V, Negativesplash10-0a4i-1101900080-9ec3eecc20f19a822002Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1901000300-57c996f08055dba75dd7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0902000000-dffb00601bfc54014ae4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2901000000-155f0890adf4c76dca85Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0arr-6820231930-984ae0f98e0d17e4a7fcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3910100000-87da6b6d742efbc6e74aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900000000-8701decc3b2311880b97Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0000000090-fd17a06b039262f96463Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05vx-9100203430-9e39d5da3afdd3a15f91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00b9-9101401200-719cb55952a06d96d3c8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0000000090-02de4c2ee732e6d50b2dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p9-1901002440-79ee9e61778bd08a750fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0209000000-84f7f68fc2e83a8ae770Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001206
FooDB IDFDB022491
Phenol Explorer IDNot Available
KNApSAcK IDC00007259
BiGG ID33558
BioCyc IDACETYL-COA
METLIN ID6082
PDB IDNot Available
Wikipedia LinkAcetyl-CoA
Chemspider ID392413
ChEBI ID15351
PubChem Compound ID444493
Kegg Compound IDC00024
YMDB IDYMDB00312
ECMDB IDECMDB01206
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. 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.
2. 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.
3. 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.
4. 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.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.
12. 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.
13. Peters SJ: Regulation of PDH activity and isoform expression: diet and exercise. Biochem Soc Trans. 2003 Dec;31(Pt 6):1274-80.
14. 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.
15. 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.
16. 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.
17. 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.
18. 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.
19. 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.
20. 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.
21. 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.
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27. https://www.ncbi.nlm.nih.gov/pubmed/?term=16708165
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34. https://www.ncbi.nlm.nih.gov/pubmed/?term=19914586
35. https://www.ncbi.nlm.nih.gov/pubmed/?term=3950616