Record Information
Version1.0
Creation date2011-09-21 00:16:54 UTC
Update date2019-11-26 03:21:04 UTC
Primary IDFDB022614
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCoenzyme A
DescriptionCoenzyme A (CoA, CoASH, or HSCoA) is a coenzyme, notable for its role in the synthesis and oxidization of fatty acids, and the oxidation of pyruvate in the citric acid cycle. It is adapted from beta-mercaptoethylamine, panthothenate and adenosine triphosphate. Acetyl-CoA is an important molecule itself. It is the precursor to HMG CoA, which is a vital component in cholesterol and ketone synthesis. Furthermore, it contributes an acetyl group to choline to produce acetylcholine, in a reaction catalysed by choline acetyltransferase. Its main task is conveying the carbon atoms within the acetyl group to the citric acid cycle to be oxidized for energy production. -- Wikipedia [HMDB]. Coenzyme A is found in many foods, some of which are grape, cowpea, pili nut, and summer savory.
CAS Number85-61-0
Structure
Thumb
Synonyms
SynonymSource
CoAMeSH
CoASHMeSH
Acetoacetyl coenzyme A sodium saltHMDB
CoA HydrateHMDB
CoA-SHHMDB
coenzyme A HydrateHMDB
coenzyme A-SHHMDB
coenzyme ASHHMDB
Coenzymes aHMDB
Depot-zeelHMDB
Propionyl CoAHMDB
Propionyl coenzyme AHMDB
S-PropanoateHMDB
S-Propanoate CoAHMDB
S-Propanoate coenzyme AHMDB
S-Propanoic acidHMDB
S-Propionate CoAHMDB
S-Propionate coenzyme AHMDB
ZeelHMDB
[(2R,3S,4R,5R)-5-(6-amino-9H-Purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl 3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphateHMDB
a, CoenzymeMeSH
[(2R,3S,4R,5R)-5-(6-amino-9H-Purin-9-yl)-4-hydroxy-3-(onooxy)tetrahydrofuran-2-yl]methyl 3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diateHMDB
[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)tetrahydrofuran-2-yl]methyl 3-hydroxy-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)-2,2-dimethyl-4-oxobutyl dihydrogen diphosphatehmdb
CoA hydratehmdb
Coenzyme Ahmdb
Coenzyme A hydratehmdb
Coenzyme A-SHhmdb
Coenzyme ASHhmdb
coenzymes Ahmdb
Depot-Zeelhmdb
Propionyl Coenzyme Ahmdb
S-propanoatehmdb
S-propanoate CoAhmdb
S-propanoate Coenzyme Ahmdb
S-propanoic acidhmdb
S-propionate CoAhmdb
S-propionate Coenzyme Ahmdb
Predicted Properties
PropertyValueSource
Water Solubility5.35 g/LALOGPS
logP-0.63ALOGPS
logP-5.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area346.56 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity162.74 m³·mol⁻¹ChemAxon
Polarizability66.82 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC21H36N7O16P3S
IUPAC name{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[3-hydroxy-2,2-dimethyl-3-({2-[(2-sulfanylethyl)carbamoyl]ethyl}carbamoyl)propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
InChI IdentifierInChI=1S/C21H36N7O16P3S/c1-21(2,16(31)19(32)24-4-3-12(29)23-5-6-48)8-41-47(38,39)44-46(36,37)40-7-11-15(43-45(33,34)35)14(30)20(42-11)28-10-27-13-17(22)25-9-26-18(13)28/h9-11,14-16,20,30-31,48H,3-8H2,1-2H3,(H,23,29)(H,24,32)(H,36,37)(H,38,39)(H2,22,25,26)(H2,33,34,35)/t11-,14-,15-,16?,20-/m1/s1
InChI KeyRGJOEKWQDUBAIZ-DRCCLKDXSA-N
Isomeric SMILESCC(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)C(O)C(=O)NCCC(=O)NCCS
Average Molecular Weight767.534
Monoisotopic Molecular Weight767.115208365
Classification
Description Belongs to the class of organic compounds known as coenzyme a and derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassPurine ribonucleotides
Direct ParentCoenzyme A and derivatives
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • 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
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Fatty amide
  • Monosaccharide
  • N-acyl-amine
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Fatty acyl
  • Imidolactam
  • Alkyl phosphate
  • Phosphoric acid ester
  • Pyrimidine
  • Tetrahydrofuran
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Carboxamide group
  • Alkylthiol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxide
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organosulfur compound
  • Alcohol
  • Amine
  • Organopnictogen compound
  • Primary amine
  • Organic oxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
OntologyNo ontology term
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
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSCoenzyme A, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-9423572000-e15b71f4fd7a2baa5a35Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0000000900-7edeffc9e7f47049c6af2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0090200000-1bf2c11b25a8c3f528a72012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03di-0490000000-b4270769e635660752dd2012-07-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002s-5900000100-c920e6430f49f066a6442016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002r-6910000000-4dcac54e50dd5309af5c2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002r-8900000000-c9fc1dcc0fa2fecbf2f02016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-6910232700-7e01b474d15249f13f3e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2900200000-23c6af6438be416c3b4e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-6900100000-a9a1d2f2162117f6ad812016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID6557
ChEMBL IDCHEMBL1623949
KEGG Compound IDC00010
Pubchem Compound ID6816
Pubchem Substance IDNot Available
ChEBI ID15346
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01423
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID33502
KNApSAcK IDNot Available
HET ID1A59
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDCoenzyme A
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
Serine palmitoyltransferase 1SPTLC1O15269
Carnitine O-acetyltransferaseCRATP43155
Peroxisomal carnitine O-octanoyltransferaseCROTQ9UKG9
Carnitine O-palmitoyltransferase 1, muscle isoformCPT1BQ92523
Carnitine O-palmitoyltransferase 1, liver isoformCPT1AP50416
Carnitine O-palmitoyltransferase 2, mitochondrialCPT2P23786
Carnitine O-palmitoyltransferase 1, brain isoformCPT1CQ8TCG5
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
Fatty acid synthaseFASNP49327
Sterol O-acyltransferase 1SOAT1P35610
Lysosomal thioesterase PPT2PPT2Q9UMR5
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
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-oxoglutarate dehydrogenase, mitochondrialOGDHQ02218
2-oxoglutarate dehydrogenase-like, mitochondrialOGDHLQ9ULD0
Arylamine N-acetyltransferase 1NAT1P18440
Arylamine N-acetyltransferase 2NAT2P11245
3-hydroxy-3-methylglutaryl-coenzyme A reductaseHMGCRP04035
Ceramide synthase 1CERS1P27544
Phosphatidylinositol-glycan biosynthesis class W proteinPIGWQ7Z7B1
Acetyl-coenzyme A synthetase, cytoplasmicACSS2Q9NR19
Acetyl-coenzyme A synthetase 2-like, mitochondrialACSS1Q9NUB1
Dihydrolipoyllysine-residue acetyltransferase component of pyruvate dehydrogenase complex, mitochondrialDLATP10515
Acyl-coenzyme A thioesterase 12ACOT12Q8WYK0
Palmitoyl-protein thioesterase 1PPT1P50897
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
Elongation of very long chain fatty acids protein 4ELOVL4Q9GZR5
N-acetylglutamate synthase, mitochondrialNAGSQ8N159
Nuclear receptor coactivator 3NCOA3Q9Y6Q9
Serine palmitoyltransferase 2SPTLC2O15270
Serine palmitoyltransferase 3SPTLC3Q9NUV7
Bile acyl-CoA synthetaseSLC27A5Q9Y2P5
Sterol O-acyltransferase 2SOAT2O75908
Bifunctional coenzyme A synthaseCOASYQ13057
Acetoacetyl-CoA synthetaseAACSQ86V21
3-hydroxyisobutyryl-CoA hydrolase, mitochondrialHIBCHQ6NVY1
L-aminoadipate-semialdehyde dehydrogenase-phosphopantetheinyl transferaseAASDHPPTQ9NRN7
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
Very long-chain acyl-CoA synthetaseSLC27A2O14975
Non-specific lipid-transfer proteinSCP2P22307
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
Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex, mitochondrialDLSTP36957
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
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
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
Malonyl-CoA-acyl carrier protein transacylase, mitochondrialMCATQ8IVS2
Glycylpeptide N-tetradecanoyltransferase 1NMT1P30419
Glycylpeptide N-tetradecanoyltransferase 2NMT2O60551
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045 map00520
Beta Oxidation of Very Long Chain Fatty AcidsSMP00052 map01040
Beta-Alanine MetabolismSMP00007 map00410
Bile Acid BiosynthesisSMP00035 map00120
Butyrate MetabolismSMP00073 map00650
Citric Acid CycleSMP00057 map00020
Ethanol DegradationSMP00449 Not Available
Fatty acid MetabolismSMP00051 map00071
Glycine and Serine MetabolismSMP00004 map00260
Ketone Body MetabolismSMP00071 map00072
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
Pantothenate and CoA BiosynthesisSMP00027 map00770
Phenylacetate MetabolismSMP00126 map00360
Plasmalogen SynthesisSMP00479 Not Available
Threonine and 2-Oxobutanoate DegradationSMP00452 Not Available
Transfer of Acetyl Groups into MitochondriaSMP00466 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference