Record Information |
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Version |
1.0 |
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Update Date |
1/22/2018 12:54:54 PM |
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Metabolite ID | PAMDB110248 |
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Identification |
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Name: |
coenzyme A |
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Description: | Tetraanion of coenzyme A. |
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Structure |
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Synonyms: | -
HS-CoA
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CoA
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co-A-SH
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co-enzyme-A
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co-A
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Chemical Formula: |
C21H32N7O16P3S
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Average Molecular Weight: |
763.5 |
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Monoisotopic Molecular
Weight: |
767.1152083656 |
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InChI Key: |
RGJOEKWQDUBAIZ-IBOSZNHHSA-J |
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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 |
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CAS
number: |
85-61-0 |
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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} |
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Traditional IUPAC Name: |
coenzyme A |
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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-] |
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Chemical Taxonomy |
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Taxonomy Description | This 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. |
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Kingdom |
Chemical entities |
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Super Class | Organic compounds |
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Class |
Nucleosides, nucleotides, and analogues |
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Sub Class | Purine nucleotides |
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Direct Parent |
Coenzyme A and derivatives |
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Alternative Parents |
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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
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Molecular Framework |
Aromatic heteropolycyclic compounds |
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External Descriptors |
Not Available |
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Physical Properties |
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State: |
Solid |
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Charge: | -4 |
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Melting point: |
Not Available |
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Experimental Properties: |
Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties |
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Biological Properties |
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Cellular Locations: |
Not Available |
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Reactions: | succinyl-CoA + acetyl-CoA → 3-oxoadipyl-CoA + coenzyme AOPC6-CoA + acetyl-CoA → OPC8-3-ketoacyl-CoA + coenzyme Amalonyl-CoA + Hydrogen ion → Carbon dioxide + coenzyme Acoenzyme A + propanoate + ATP → propanoyl-CoA + diphosphate + AMP3-trans,5-cis-tetradecadienoyl-CoA + Water → Hydrogen ion + (3E,5Z)-tetradecadienoate + coenzyme AOPC4-CoA + acetyl-CoA → OPC6-3-ketoacyl-CoA + coenzyme Alinoleate + coenzyme A + ATP → linoleoyl-CoA + diphosphate + AMP5-methyl-3-oxo-4-hexenoyl-CoA + coenzyme A → 3-methylcrotonyl-CoA + acetyl-CoAjasmonoyl-CoA + acetyl-CoA → OPC4-3-ketoacyl-CoA + coenzyme AATP + α-linolenate + coenzyme A → α-linolenoyl-CoA + diphosphate + AMP3-amino-4-hydroxybenzoate + acetyl-CoA → 3-acetylamino-4-hydroxybenzoate + coenzyme A3-oxopropanoate + coenzyme A + NAD+ → acetyl-CoA + Carbon dioxide + NADHoleate + coenzyme A + ATP → oleoyl-CoA + AMP + diphosphate4-hydroxybenzoyl-CoA + acetyl-CoA → 4-hydroxybenzoyl-acetyl-CoA + coenzyme Apalmitoyl-CoA + Water → Hydrogen ion + palmitate + coenzyme Acoenzyme A → octanoyl-CoAbutanoyl-CoA + acetyl-CoA → 3-oxohexanoyl-CoA + coenzyme A2-methylacetoacetyl-CoA + coenzyme A → propanoyl-CoA + acetyl-CoA2-Keto-3-methyl-valerate + NAD+ + coenzyme A → 2-methylbutanoyl-CoA + NADH + Carbon dioxideLong-Chain-Fatty-Acids + coenzyme A + ATP → Long-Chain-Acyl-CoAs + diphosphate + AMPeicosapentaenoate + ATP + coenzyme A → eicosapentaenoyl-CoA + diphosphate + AMPjasmonoyl-CoA + Water → Hydrogen ion + (+)-7-iso-jasmonate + coenzyme Ahexadecanedioyl-CoA + sn-glycerol 3-phosphate → coenzyme A + 1-C16:0-α,ω-dicaboxyl-2-lysophosphatidate3-oxo-23,24-bisnorchol-4-en-22-oyl-CoA + acetyl-CoA → 3,22-dioxochol-4-en-24-oyl-CoA + coenzyme AAryl-Amines + acetyl-CoA → N-acetylarylamines + coenzyme Aacetyl-CoA + propanoyl-CoA → β-ketovaleryl-CoA + coenzyme AL-ornithine + succinyl-CoA → Hydrogen ion + N2-succinyl-L-ornithine + coenzyme A3-oxocholest-4-en-26-oate + ATP + coenzyme A → 3-oxocholest-4-en-26-oyl-CoA + AMP + diphosphatedecanoyl-CoA + acetyl-CoA → 3-oxododecanoyl-CoA + coenzyme Ahexanoyl-CoA + acetyl-CoA → 3-oxooctanoyl-CoA + coenzyme Aacetyl-CoA + spermine → N1-acetylspermine + coenzyme A + Hydrogen ionarachidoyl-CoA + Hydrogen ion → coenzyme A + Carbon dioxideCPD66-39 + coenzyme A + ATP → Saturated-Fatty-Acyl-CoA + diphosphate + AMP3-cis-dodecenoyl-CoA + acetyl-CoA → 3-keto-5-cis-tetradecenoyl-CoA + coenzyme Aphytenate + ATP + coenzyme A → phytenoyl-CoA + AMP + diphosphatePropanal + coenzyme A + NAD+ → propanoyl-CoA + NADH + Hydrogen iondihomo γ-linolenoyl-CoA + Water → di-homo-γ-linolenate + coenzyme A + Hydrogen ion6-cis, 3-oxo-tridecenoyl-CoA + coenzyme A → 4-cis-undecenoyl-CoA + acetyl-CoA6-trans-3-oxo-tridecenoyl-CoA + coenzyme A → 4-trans-undecenoyl-CoA + acetyl-CoAacetyl-CoA + spermidine → N1-acetylspermidine + Hydrogen ion + coenzyme A4-trans-3-oxo-undecenoyl-CoA + coenzyme A → 2-trans-nonenoyl-CoA + acetyl-CoA5-trans-3-oxo-dodecenoyl-CoA + coenzyme A → 3-trans-decenoyl-CoA + acetyl-CoA5-cis, 7-trans-3-oxo-tetradecadienoyl-CoA + coenzyme A → 3-cis, 5-trans-dodecadienoyl-CoA + acetyl-CoAphenylacetate + ATP + coenzyme A → phenylacetyl-CoA + AMP + diphosphateL-Methionine + acetyl-CoA → N-α-acetyl-L-methionine + coenzyme A + Hydrogen ionACYL-COA + Water → coenzyme A + Carboxylates + Hydrogen ionR2OH-Straight-Chain-234-Sat-FA + ATP + coenzyme A → R2-2OH-Straight-Chain-234-Sat-FA-CoA + AMP + diphosphate7-methyl-3-oxooct-6-enoyl-CoA + coenzyme A → 5-methylhex-4-enoyl-CoA + acetyl-CoAstearoyl-CoA + Water → Hydrogen ion + Octadecanoate (N-C18:0) + coenzyme Acoenzyme A → (R)-3-hydroxydecanoyl-CoA(15Z)-tetracosenoate + coenzyme A + ATP → (Z)-15-tetracosenoyl-CoA + diphosphate + AMPoxaloacetate + Water + propanoyl-CoA → Hydrogen ion + (2S,3S)-2-methylcitrate + coenzyme Acyclohexane-1-carbonyl-CoA + Water → cyclohexane-1-carboxylate + coenzyme A + Hydrogen ionpalmitate + coenzyme A + ATP → palmitoyl-CoA + diphosphate + AMP1-oleyl-2-lyso-phosphatidate + oleoyl-CoA → 1-18:1-2-18:1-phosphatidate + coenzyme A3-[(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 + diphosphatepristanate + coenzyme A + ATP → pristanoyl-CoA + diphosphate + AMPglycerone phosphate + oleoyl-CoA → 1-oleoyl-2-lyso-glycerone phosphate + coenzyme Aacetyl-CoA + putrescine → N-acetylputrescine + coenzyme A + Hydrogen ion2-Me-Branched-234-Sat-FA + coenzyme A + ATP → 2-Me-Branched-234-Sat-Fatty-Acyl-CoA + diphosphate + AMP2,3-didehydroadipyl-CoA + acetyl-CoA → 3-oxo-5,6-didehydrosuberyl-CoA + coenzyme A More...
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Pathways: |
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Spectra |
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Spectra: |
Spectrum Type | Description | Splash Key | |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-014i-0000000900-7edeffc9e7f47049c6af | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-03di-0090200000-1bf2c11b25a8c3f528a7 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-03di-0490000000-b4270769e635660752dd | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | Not Available |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | Not Available |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | Not Available |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | Not Available |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | Not Available |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | Not Available |
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1D NMR | 1H NMR Spectrum | Not Available |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available |
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References |
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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 ]
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Synthesis Reference: |
Not Available |
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Material Safety Data Sheet (MSDS) |
Download (PDF) |
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Links |
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External Links: |
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