Record Information
Version1.0
Creation date2011-09-21 00:14:50 UTC
Update date2019-11-26 03:21:03 UTC
Primary IDFDB022491
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameAcetyl-CoA
DescriptionThe 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. [HMDB]. Acetyl-CoA is found in many foods, some of which are grapefruit/pummelo hybrid, oriental wheat, ostrich fern, and jute.
CAS Number72-89-9
Structure
Thumb
Synonyms
SynonymSource
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
ac-CoAhmdb
ac-Coenzyme Ahmdb
ac-S-CoAhmdb
ac-S-Coenzyme Ahmdb
acetyl coenzyme-Ahmdb
acetyl-CoAhmdb
acetyl-Coenzyme Ahmdb
acetyl-S-CoAhmdb
acetyl-S-Coenzyme Ahmdb
acetylcoenzyme-Ahmdb
S-acetate CoAhmdb
S-acetate Coenzyme Ahmdb
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 FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC23H38N7O17P3S
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
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
Isomeric 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
Average Molecular Weight809.571
Monoisotopic Molecular Weight809.125773051
Classification
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentAcyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside 3',5'-bisphosphate
  • Purine ribonucleoside bisphosphate
  • Purine ribonucleoside diphosphate
  • Ribonucleoside 3'-phosphate
  • Pentose phosphate
  • Pentose-5-phosphate
  • Beta amino acid or derivatives
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Pyrimidine
  • Alkyl phosphate
  • Fatty amide
  • Phosphoric acid ester
  • Tetrahydrofuran
  • Imidazole
  • Azole
  • Heteroaromatic compound
  • Carbothioic s-ester
  • Secondary alcohol
  • Thiocarboxylic acid ester
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Organosulfur compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic nitrogen compound
  • Primary amine
  • Organopnictogen compound
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Alcohol
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1901000300-57c996f08055dba75dd7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0902000000-dffb00601bfc54014ae4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-2901000000-155f0890adf4c76dca85JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0arr-6820231930-984ae0f98e0d17e4a7fcJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-3910100000-87da6b6d742efbc6e74aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-5900000000-8701decc3b2311880b97JSpectraViewer
ChemSpider ID392413
ChEMBL IDNot Available
KEGG Compound IDC00024
Pubchem Compound ID444493
Pubchem Substance IDNot Available
ChEBI ID15351
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01206
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID33558
KNApSAcK IDNot Available
HET IDACO
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDAcetyl-CoA
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Glycine N-acyltransferaseGLYATQ6IB77
Glycine N-acyltransferase-like protein 1GLYATL1Q969I3
Glycine N-acyltransferase-like protein 2GLYATL2Q8WU03
2-amino-3-ketobutyrate coenzyme A ligase, mitochondrialGCATO75600
Bile acid-CoA:amino acid N-acyltransferaseBAATQ14032
Carnitine O-acetyltransferaseCRATP43155
Hepatic triacylglycerol lipaseLIPCP11150
Diacylglycerol O-acyltransferase 1DGAT1O75907
2-acylglycerol O-acyltransferase 2MOGAT2Q3SYC2
Diacylglycerol O-acyltransferase 2DGAT2Q96PD7
2-acylglycerol O-acyltransferase 1MOGAT1Q96PD6
2-acylglycerol O-acyltransferase 3MOGAT3Q86VF5
Glycerol-3-phosphate acyltransferase 3AGPAT9Q53EU6
Choline O-acetyltransferaseCHATP28329
Fatty acyl-CoA reductase 2FAR2Q96K12
Acyl-CoA wax alcohol acyltransferase 2AWAT2Q6E213
Serotonin N-acetyltransferaseAANATQ16613
ATP-citrate synthaseACLYP53396
Citrate synthase, mitochondrialCSO75390
Diamine acetyltransferase 2SAT2Q96F10
Diamine acetyltransferase 1SAT1P21673
Malonyl-CoA decarboxylase, mitochondrialMLYCDO95822
Fatty acid synthaseFASNP49327
Sterol O-acyltransferase 1SOAT1P35610
Peroxisome proliferator-activated receptor gammaPPARGP37231
Long-chain fatty acid transport protein 3SLC27A3Q5K4L6
Long-chain fatty acid transport protein 4SLC27A4Q6P1M0
Fatty acyl-CoA reductase 1FAR1Q8WVX9
Acyl-CoA wax alcohol acyltransferase 1AWAT1Q58HT5
Cytosolic acyl coenzyme A thioester hydrolaseACOT7O00154
Acyl-coenzyme A thioesterase 2, mitochondrialACOT2P49753
Acyl-coenzyme A thioesterase 4ACOT4Q8N9L9
Acyl-coenzyme A thioesterase 8ACOT8O14734
Acyl-coenzyme A thioesterase 1ACOT1Q86TX2
Diacylglycerol O-acyltransferase 2-like protein 6DGAT2L6Q6ZPD8
Putative diacylglycerol O-acyltransferase 2-like protein 7DGAT2L7Q6IED9
Acyl-CoA-binding proteinDBIP07108
Peroxisome proliferator-activated receptor deltaPPARDQ03181
Pyruvate dehydrogenase E1 component subunit beta, mitochondrialPDHBP11177
Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrialPDHA1P08559
Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrialPDHA2P29803
2-oxoisovalerate dehydrogenase subunit beta, mitochondrialBCKDHBP21953
Arylamine N-acetyltransferase 1NAT1P18440
Arylamine N-acetyltransferase 2NAT2P11245
Acetyl-coenzyme A synthetase, cytoplasmicACSS2Q9NR19
Acetyl-coenzyme A synthetase 2-like, mitochondrialACSS1Q9NUB1
Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrialDLATP10515
Hydroxymethylglutaryl-CoA lyase, mitochondrialHMGCLP35914
Acyl-coenzyme A thioesterase 12ACOT12Q8WYK0
Cytosolic acyl coenzyme A thioester hydrolase-likeACOT7LQ6ZUV0
Long-chain-fatty-acid--CoA ligase ACSBG2ACSBG2Q5FVE4
Long-chain-fatty-acid--CoA ligase ACSBG1ACSBG1Q96GR2
Nuclear receptor coactivator 1NCOA1Q15788
3-ketoacyl-CoA thiolase, mitochondrialACAA2P42765
Peroxisomal trans-2-enoyl-CoA reductasePECRQ9BY49
N-acetylglutamate synthase, mitochondrialNAGSQ8N159
Nuclear receptor coactivator 3NCOA3Q9Y6Q9
Bile acyl-CoA synthetaseSLC27A5Q9Y2P5
Sterol O-acyltransferase 2SOAT2O75908
Acyl-CoA synthetase family member 4AASDHQ4L235
Hydroxymethylglutaryl-CoA synthase, mitochondrialHMGCS2P54868
Hydroxymethylglutaryl-CoA synthase, cytoplasmicHMGCS1Q01581
3-oxoacyl-[acyl-carrier-protein] synthase, mitochondrialOXSMQ9NWU1
Glycerol-3-phosphate acyltransferase 1, mitochondrialGPAMQ9HCL2
Glycerol-3-phosphate acyltransferase 4AGPAT6Q86UL3
Glycerol-3-phosphate acyltransferase 2, mitochondrialGPAT2Q6NUI2
3-hydroxymethyl-3-methylglutaryl-CoA lyase, cytoplasmicHMGCLL1Q8TB92
Very long-chain acyl-CoA synthetaseSLC27A2O14975
Lysophospholipid acyltransferase 5LPCAT3Q6P1A2
Lysophosphatidylcholine acyltransferase 2LPCAT2Q7L5N7
1-acyl-sn-glycerol-3-phosphate acyltransferase gammaAGPAT3Q9NRZ7
1-acyl-sn-glycerol-3-phosphate acyltransferase betaAGPAT2O15120
1-acyl-sn-glycerol-3-phosphate acyltransferase alphaAGPAT1Q99943
1-acyl-sn-glycerol-3-phosphate acyltransferase epsilonAGPAT5Q9NUQ2
1-acyl-sn-glycerol-3-phosphate acyltransferase deltaAGPAT4Q9NRZ5
Lysocardiolipin acyltransferase 1LCLAT1Q6UWP7
Lipoamide acyltransferase component of branched-chain alpha-keto acid dehydrogenase complex, mitochondrialDBTP11182
3-ketoacyl-CoA thiolase, peroxisomalACAA1P09110
Trifunctional enzyme subunit beta, mitochondrialHADHBP55084
Dihydroxyacetone phosphate acyltransferaseGNPATO15228
Peroxisome proliferator-activated receptor alphaPPARAQ07869
Fatty acid-binding protein, heartFABP3P05413
Acyl-CoA dehydrogenase family member 10ACAD10Q6JQN1
Acyl-CoA dehydrogenase family member 11ACAD11Q709F0
Lysophospholipid acyltransferase LPCAT4LPCAT4Q643R3
Enoyl-CoA delta isomerase 2, mitochondrialECI2O75521
Nef-associated protein 1C9orf156Q9BU70
Acyl-coenzyme A thioesterase 9, mitochondrialACOT9Q9Y305
Acyl-CoA synthetase family member 3, mitochondrialACSF3Q4G176
Acyl-CoA synthetase family member 2, mitochondrialACSF2Q96CM8
Acyl-coenzyme A thioesterase 11ACOT11Q8WXI4
Glucosamine 6-phosphate N-acetyltransferaseGNPNAT1Q96EK6
Acetyl-CoA acetyltransferase, cytosolicACAT2Q9BWD1
Acetyl-CoA acetyltransferase, mitochondrialACAT1P24752
General transcription factor 3C polypeptide 4GTF3C4Q9UKN8
Histone acetyltransferase KAT2BKAT2BQ92831
Testis-specific chromodomain protein Y 1CDY1Q9Y6F8
Histone acetyltransferase KAT5KAT5Q92993
Testis-specific chromodomain protein Y 2CDY2AQ9Y6F7
Histone acetyltransferase KAT2AKAT2AQ92830
Acetyl-coenzyme A transporter 1SLC33A1O00400
Histone acetyltransferase KAT6BKAT6BQ8WYB5
MYST3 proteinMYST3A5PKX7
Histone acetyltransferase KAT8KAT8Q9H7Z6
Histone acetyltransferase type B catalytic subunitHAT1O14929
Chromodomain Y-like proteinCDYLQ9Y232
Circadian locomoter output cycles protein kaputCLOCKO15516
Histone acetyltransferase KAT7KAT7O95251
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045 map00520
Beta Oxidation of Very Long Chain Fatty AcidsSMP00052 map01040
Beta-Alanine MetabolismSMP00007 map00410
Butyrate MetabolismSMP00073 map00650
Citric Acid CycleSMP00057 map00020
Ethanol DegradationSMP00449 Not Available
Fatty Acid BiosynthesisSMP00456 Not Available
Fatty acid MetabolismSMP00051 map00071
Glycine and Serine MetabolismSMP00004 map00260
Ketone Body MetabolismSMP00071 map00072
Lysine DegradationSMP00037 map00310
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty AcidsSMP00482 Not Available
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty AcidsSMP00481 Not Available
Mitochondrial Beta-Oxidation of Short Chain Saturated Fatty AcidsSMP00480 Not Available
Oxidation of Branched Chain Fatty AcidsSMP00030 Not Available
Phytanic Acid Peroxisomal OxidationSMP00450 Not Available
Propanoate MetabolismSMP00016 map00640
Pyruvate MetabolismSMP00060 map00620
Steroid BiosynthesisSMP00023 map00100
Transfer of Acetyl Groups into MitochondriaSMP00466 Not Available
Valine, Leucine and Isoleucine DegradationSMP00032 map00280
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference