Koenzim A

Also known as CoA, CoASH, HSCoA, CoA-SH, HS-CoA

coenzyme, notable for its role in the synthesis and oxidation of fatty acids, and the oxidation of pyruvate in the citric acid cycle

OverviewAI-generated

Coenzyme A is a chemical compound with the formula C₂₁H₃₆N₇O₁₆P₃S. It has a molecular mass of 767.115209 and a weight of 767.5. The substance possesses a charge of 0 and an xlogp value of -5.8. Its structure includes 10 hydrogen bond donors and 21 hydrogen bond acceptors, with a topological polar surface area of 348.

The canonical SMILES representation for coenzyme A is 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)NCCS)O. An isomeric SMILES string is also available. The compound is associated with a PubMed query count of 34094 and is referenced by 640 other encyclopedia articles.

Synthesized by Vinony from 17 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.

In the Vinony graph

Vinony's link graph records 640 inbound references to Koenzim A, and connects out to pantothenic acid, cofactor and acyl group.

Vinony files it under Chembox image size set, Chemical articles with multiple CAS registry numbers and Chemical articles with multiple compound IDs.

Vinony links it to 40 Wikipedia language editions.

Chemical data

Formula: C21H36N7O16P3S
Molecular weight: 767.5 g/mol
IUPAC name: [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-[[3-oxo-3-(2-sulfanylethylamino)propyl]amino]butyl] hydrogen phosphate
SMILES: CC(C)(COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)[C@H](C(=O)NCCC(=O)NCCS)O
InChIKey: RGJOEKWQDUBAIZ-IBOSZNHHSA-N
XLogP: -5.8
Polar surface area: 348 Å²
H-bond donors: 10
H-bond acceptors: 21
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Phase 3
Molecule type: Small molecule
Indications: hyperlipoproteinemia, prostate cancer

via ChEMBL · EBI

Research

34,094 papers

Coenzyme A metabolism.The American journal of physiology · 1985
Hereditary diseases of coenzyme A thioester metabolism.Biochemical Society transactions · 2019
The two faces of coenzyme A in cellular biology.Free radical biology & medicine · 2025
Quantification of Coenzyme A in Cells and Tissues.Journal of visualized experiments : JoVE · 2019
Biosensors for coenzyme A thioester derivatives: Development, optimization and applications.Biotechnology advances · 2026

via PubMed

Wikidata facts

Has part: carbon
Mass: 767.115209

Show 6 more facts

Commons category: Coenzyme A
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)NCCS)O
chemical formula: C₂₁H₃₆N₇O₁₆P₃S
found in taxon: Caenorhabditis elegans
isomeric SMILES: CC(C)(COP(=O)(O)OP(=O)(O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=NC3=C(N=CN=C32)N)O)OP(=O)(O)O)[C@H](C(=O)NCCC(=O)NCCS)O
subject has role: primary metabolite

Sources (4)

via Wikidata · CC0