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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.
In the Vinony graph
Vinony's link graph records 31 inbound references to benzoyl-CoA, and connects out to International Standard Book Number, digital object identifier and chemical formula.
It sits within the topics Chembox image size set and Thioesters of coenzyme A.
Vinony links it to 7 Wikipedia language editions.
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.