coenzyme A (PAMDB110248)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110248
Identification
Name: coenzyme A
Description:Tetraanion of coenzyme A.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • HS-CoA
  • CoA
  • co-A-SH
  • co-enzyme-A
  • co-A
Chemical Formula: C21H32N7O16P3S
Average Molecular Weight: 763.5
Monoisotopic Molecular Weight: 767.1152083656
InChI Key: RGJOEKWQDUBAIZ-IBOSZNHHSA-J
InChI: InChI=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)/p-4/t11-,14-,15-,16+,20-/m1/s1
CAS number: 85-61-0
IUPAC Name:3'-phosphonatoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-({3-oxo-3-[(2-sulfanylethyl)amino]propyl}amino)butyl] diphosphate}
Traditional IUPAC Name: coenzyme A
SMILES:CC(C)(C(O)C(=O)NCCC(=O)NCCS)COP(=O)(OP(=O)(OCC1(OC(C(C1OP([O-])(=O)[O-])O)N3(C2(=C(C(N)=NC=N2)N=C3))))[O-])[O-]
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as coenzyme a and derivatives. These are derivative of vitamin B5 containing a 4'-phosphopantetheine moiety attached to a diphospho-adenosine.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Nucleosides, nucleotides, and analogues
Sub ClassPurine nucleotides
Direct Parent Coenzyme 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
  • Primary aromatic amine
  • Pyrimidine
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Oxolane
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Amino acid or derivatives
  • Alkylthiol
  • Organoheterocyclic compound
  • Azacycle
  • Oxacycle
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organosulfur compound
  • Hydrocarbon derivative
  • Alcohol
  • Amine
  • Organopnictogen compound
  • Primary amine
  • Carbonyl group
  • Organic oxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors Not Available
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 Solubility4.64 mg/mLALOGPS
logP-0.61ALOGPS
logP-6.8ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area346.56 Å2ChemAxon
Rotatable Bond Count18ChemAxon
Refractivity162.74 m3·mol-1ChemAxon
Polarizability66.81 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
Odd-Straight-Chain-234-Sat-FA + ATP + coenzyme A → Odd-Saturated-Fatty-Acyl-CoA + AMP + diphosphate
Citronellates + coenzyme A + ATP → citronellyll-CoA + AMP + diphosphate
coenzyme A + acetoacetate + ATP → acetoacetyl-CoA + diphosphate + AMP
3-amino-4-hydroxybenzaldehyde + acetyl-CoA → Hydrogen ion + 3-acetylamino-4-hydroxybenzaldehyde + coenzyme A
coenzyme A + acetate + ATP → phosphate + acetyl-CoA + ADP
malonyl-CoA → coenzyme A
3-Methyl-Saturated-Fatty-Acids + coenzyme A + ATP → 3-Methyl-Saturated-Fatty-Acyl-CoA + AMP + diphosphate
sn-glycerol 3-phosphate + oleoyl-CoA → 1-oleyl-2-lyso-phosphatidate + coenzyme A
2-methylbutanoyl-CoA + BCAA-dehydrogenase-DH-lipoyl → BCAA-dehydrogenase-2MB-DH-lipoyl + coenzyme A
acetyl-CoA + Hydrogen ion → coenzyme A + Carbon dioxide
eicosapentaenoyl-CoA + Water → eicosapentaenoate + coenzyme A + Hydrogen ion
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
trans-cinnamate + coenzyme A + ATP → (E)-cinnamoyl-CoA + AMP + diphosphate
Hydrogen ion + Glycine + succinyl-CoA → Carbon dioxide + coenzyme A + 5-Aminolevulinic acid
succinyl-CoA + acetyl-CoA → 3-oxoadipyl-CoA + coenzyme A
OPC6-CoA + acetyl-CoA → OPC8-3-ketoacyl-CoA + coenzyme A
malonyl-CoA + Hydrogen ion → Carbon dioxide + coenzyme A
coenzyme A + propanoate + ATP → propanoyl-CoA + diphosphate + AMP
3-trans,5-cis-tetradecadienoyl-CoA + Water → Hydrogen ion + (3E,5Z)-tetradecadienoate + coenzyme A
OPC4-CoA + acetyl-CoA → OPC6-3-ketoacyl-CoA + coenzyme A
linoleate + coenzyme A + ATP → linoleoyl-CoA + diphosphate + AMP
5-methyl-3-oxo-4-hexenoyl-CoA + coenzyme A → 3-methylcrotonyl-CoA + acetyl-CoA
jasmonoyl-CoA + acetyl-CoA → OPC4-3-ketoacyl-CoA + coenzyme A
ATP + α-linolenate + coenzyme A → α-linolenoyl-CoA + diphosphate + AMP
3-amino-4-hydroxybenzoate + acetyl-CoA → 3-acetylamino-4-hydroxybenzoate + coenzyme A
3-oxopropanoate + coenzyme A + NAD+ → acetyl-CoA + Carbon dioxide + NADH
oleate + coenzyme A + ATP → oleoyl-CoA + AMP + diphosphate
4-hydroxybenzoyl-CoA + acetyl-CoA → 4-hydroxybenzoyl-acetyl-CoA + coenzyme A
palmitoyl-CoA + Water → Hydrogen ion + palmitate + coenzyme A
coenzyme A → octanoyl-CoA
butanoyl-CoA + acetyl-CoA → 3-oxohexanoyl-CoA + coenzyme A
2-methylacetoacetyl-CoA + coenzyme A → propanoyl-CoA + acetyl-CoA
2-Keto-3-methyl-valerate + NAD+ + coenzyme A → 2-methylbutanoyl-CoA + NADH + Carbon dioxide
Long-Chain-Fatty-Acids + coenzyme A + ATP → Long-Chain-Acyl-CoAs + diphosphate + AMP
eicosapentaenoate + ATP + coenzyme A → eicosapentaenoyl-CoA + diphosphate + AMP
jasmonoyl-CoA + Water → Hydrogen ion + (+)-7-iso-jasmonate + coenzyme A
hexadecanedioyl-CoA + sn-glycerol 3-phosphate → coenzyme A + 1-C16:0-α,ω-dicaboxyl-2-lysophosphatidate
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
L-ornithine + succinyl-CoA → Hydrogen ion + N2-succinyl-L-ornithine + coenzyme A
3-oxocholest-4-en-26-oate + ATP + coenzyme A → 3-oxocholest-4-en-26-oyl-CoA + AMP + diphosphate
decanoyl-CoA + acetyl-CoA → 3-oxododecanoyl-CoA + coenzyme A
hexanoyl-CoA + acetyl-CoA → 3-oxooctanoyl-CoA + coenzyme A
acetyl-CoA + spermine → N1-acetylspermine + coenzyme A + Hydrogen ion
arachidoyl-CoA + Hydrogen ion → coenzyme A + Carbon dioxide
CPD66-39 + coenzyme A + ATP → Saturated-Fatty-Acyl-CoA + diphosphate + AMP
3-cis-dodecenoyl-CoA + acetyl-CoA → 3-keto-5-cis-tetradecenoyl-CoA + coenzyme A
phytenate + ATP + coenzyme A → phytenoyl-CoA + AMP + diphosphate
Propanal + coenzyme A + NAD+ → propanoyl-CoA + NADH + Hydrogen ion
dihomo γ-linolenoyl-CoA + Water → di-homo-γ-linolenate + coenzyme A + Hydrogen ion
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
phenylacetate + ATP + coenzyme A → phenylacetyl-CoA + AMP + diphosphate
L-Methionine + acetyl-CoA → N-α-acetyl-L-methionine + coenzyme A + Hydrogen ion
ACYL-COA + Water → coenzyme A + Carboxylates + Hydrogen ion
R2OH-Straight-Chain-234-Sat-FA + ATP + coenzyme A → R2-2OH-Straight-Chain-234-Sat-FA-CoA + AMP + diphosphate
7-methyl-3-oxooct-6-enoyl-CoA + coenzyme A → 5-methylhex-4-enoyl-CoA + acetyl-CoA
stearoyl-CoA + Water → Hydrogen ion + Octadecanoate (N-C18:0) + coenzyme A
coenzyme A → (R)-3-hydroxydecanoyl-CoA
(15Z)-tetracosenoate + coenzyme A + ATP → (Z)-15-tetracosenoyl-CoA + diphosphate + AMP
oxaloacetate + Water + propanoyl-CoA → Hydrogen ion + (2S,3S)-2-methylcitrate + coenzyme A
cyclohexane-1-carbonyl-CoA + Water → cyclohexane-1-carboxylate + coenzyme A + Hydrogen ion
palmitate + coenzyme A + ATP → palmitoyl-CoA + diphosphate + AMP
1-oleyl-2-lyso-phosphatidate + oleoyl-CoA → 1-18:1-2-18:1-phosphatidate + coenzyme A
3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoate + ATP + coenzyme A → 3-[(3aS,4S,7aS)-7a-methyl-1,5-dioxo-octahydro-1H-inden-4-yl]propanoyl-CoA + AMP + diphosphate
pristanate + coenzyme A + ATP → pristanoyl-CoA + diphosphate + AMP
glycerone phosphate + oleoyl-CoA → 1-oleoyl-2-lyso-glycerone phosphate + coenzyme A
acetyl-CoA + putrescine → N-acetylputrescine + coenzyme A + Hydrogen ion
2-Me-Branched-234-Sat-FA + coenzyme A + ATP → 2-Me-Branched-234-Sat-Fatty-Acyl-CoA + diphosphate + AMP
2,3-didehydroadipyl-CoA + acetyl-CoA → 3-oxo-5,6-didehydrosuberyl-CoA + coenzyme A
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-014i-0000000900-7edeffc9e7f47049c6afView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-0090200000-1bf2c11b25a8c3f528a7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03di-0490000000-b4270769e635660752ddView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Wendel U, Zass R, Leupold D: Contribution of odd-numbered fatty acid oxidation to propionate production in neonates with methylmalonic and propionic acidaemias. Eur J Pediatr. 1993 Dec;152(12):1021-3. [8131803 ]
  • Bergstrom T, Greter J, Levin AH, Steen G, Tryding N, Wass U: Propionyl-CoA carboxylase deficiency: case report, effect of low-protein diet and identification of 3-oxo-2-methylvaleric acid 3-hydroxy-2-methylvaleric acid, and maleic acid in urine. Scand J Clin Lab Invest. 1981 Apr;41(2):117-26. [7313494 ]
  • 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 ]
  • Yano S, Li L, Le TP, Moseley K, Guedalia A, Lee J, Gonzalez I, Boles RG: Infantile mitochondrial DNA depletion syndrome associated with methylmalonic aciduria and 3-methylcrotonyl-CoA and propionyl-CoA carboxylase deficiencies in two unrelated patients: a new phenotype of mtDNA depletion syndrome. J Inherit Metab Dis. 2003;26(5):481-8. [14518828 ]
  • Kretschmer RE, Bachmann C: Methylcitric acid determination in amniotic fluid by electron-impact mass fragmentography. J Clin Chem Clin Biochem. 1988 May;26(5):345-8. [3404093 ]
  • Osmundsen H, Bremer J, Pedersen JI: Metabolic aspects of peroxisomal beta-oxidation. Biochim Biophys Acta. 1991 Sep 11;1085(2):141-58. [1892883 ]
  • Reihner E, Angelin B, Rudling M, Ewerth S, Bjorkhem I, Einarsson K: Regulation of hepatic cholesterol metabolism in humans: stimulatory effects of cholestyramine on HMG-CoA reductase activity and low density lipoprotein receptor expression in gallstone patients. J Lipid Res. 1990 Dec;31(12):2219-26. [2090716 ]
  • Salen G, Batta AK, Tint GS, Shefer S: Comparative effects of lovastatin and chenodeoxycholic acid on plasma cholestanol levels and abnormal bile acid metabolism in cerebrotendinous xanthomatosis. Metabolism. 1994 Aug;43(8):1018-22. [8052141 ]
  • Lehnert W, Junker A: [2-Methyl-3-oxovaleric acid: a characteristic metabolite in propionic acidemia] Clin Chim Acta. 1980 May 21;104(1):47-51. [7389125 ]
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CAS85-61-0
ChEBI57287
HMDBHMDB01423
IAF126033502
KEGGC00010
KNApSAcKC00007258
MetaboLightsMTBLC57287
PubChem25113190
WikipediaCoenzyme_a