Structure via PubChem · Public domain (PubChem)
benzoyl-CoA
Sign in to saveBenzoyl-CoA is the thioester derived from benzoic acid and coenzyme A. The term benzoyl-CoA also include diverse conjugates of coenzyme A and aromatic carboxylic acids. Benzoate, vanillin, anthranilic acid, 4-ethylphenol, p-cresol, phenol, aniline, terephthalic acid, [3-hydroxybenzoic acid, and phenylalanine are all metabolized to benzoyl-CoA. Additionally, cinnamic acid, p-coumaric acid, ferulic acid, toluene, caffeic acid, benzyl alcohol, and mandelic acid are suspected to be processed similarly.
Chemical data
- Formula
- C28H36N7O17P3S-4
- Molecular weight
- 867.6 g/mol
- IUPAC name
- [5-(6-aminopurin-9-yl)-2-[[[[4-[[3-(2-benzoylsulfanylethylamino)-3-oxopropyl]amino]-3-hydroxy-2,2-dimethyl-4-oxobutoxy]-oxidophosphoryl]oxy-oxidophosphoryl]oxymethyl]-4-hydroxyoxolan-3-yl] phosphate
- SMILES
- CC(C)(COP(=O)([O-])OP(=O)([O-])OCC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)([O-])[O-])C(C(=O)NCCC(=O)NCCSC(=O)C4=CC=CC=C4)O
- InChIKey
- VEVJTUNLALKRNO-UHFFFAOYSA-J
- XLogP
- -4.3
- Polar surface area
- 400 Ų
- H-bond donors
- 5
- H-bond acceptors
- 22
- Formal charge
- -4
via PubChem
Wikidata facts
- Mass
- 867.1123179016404
Show 2 more facts
- canonical SMILES
- CC(C)(COP(=O)([O-])OP(=O)([O-])OCC1C(C(C(O1)N2C=NC3=C2N=CN=C3N)O)OP(=O)([O-])[O-])C(C(=O)NCCC(=O)NCCSC(=O)C4=CC=CC=C4)O
- chemical formula
- C₂₈H₃₆N₇O₁₇P₃S⁴⁻
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- As substrate for reductases
- As a benzoyl donor
- References
Benzoyl-CoA is the thioester derived from benzoic acid and coenzyme A. The term benzoyl-CoA also include diverse conjugates of coenzyme A and aromatic carboxylic acids. Benzoate, vanillin, anthranilic acid, 4-ethylphenol, p-cresol, phenol, aniline, terephthalic acid, [3-hydroxybenzoic acid, and phenylalanine are all metabolized to benzoyl-CoA. Additionally, cinnamic acid, p-coumaric acid, ferulic acid, toluene, caffeic acid, benzyl alcohol, and mandelic acid are suspected to be processed similarly.
==As substrate for reductases== thumb|Benzoyl CoA is processed anaerobically to the cyclohexadiene derivative.|center|400px Benzoyl-CoA is a substrate for diverse reductases: 4-hydroxybenzoyl-CoA reductase, benzoyl-CoA reductase, benzoyl-CoA 3-monooxygenase, benzoate-CoA ligase, 2alpha-hydroxytaxane 2-O-benzoyltransferase, anthranilate N-benzoyltransferase, biphenyl synthase, glycine N-benzoyltransferase, ornithine N-benzoyltransferase and phenylglyoxylate dehydrogenase (acylating). Benzoyl-CoA reductase converts benzoyl-CoA to cyclohex-1,5-diene-1-carbonyl-CoA, which is susceptible to hydrolysis, eventually giving acetyl coenzyme A. In this way, many aromatic compounds are biodegraded.
Excerpted from Wikipedia’s “benzoyl-CoA” article, available under the CC BY-SA 4.0 licence.