coenzyme 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.

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

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

~10 min read

Encyclopedic overview

Coenzyme A (CoA, SHCoA, CoASH) is a coenzyme, notable for its role in the synthesis and oxidation of fatty acids, and the oxidation of pyruvate in the citric acid cycle. Every genome sequenced to date encodes enzymes that use coenzyme A as a substrate, and around 4% of cellular enzymes use it (or a thioester) as a substrate. In humans, CoA biosynthesis requires cysteine, pantothenate (vitamin B5), and adenosine triphosphate (ATP).

In its acetyl form, coenzyme A is a highly versatile molecule, serving metabolic functions in both the anabolic and catabolic pathways. Acetyl-CoA is utilised in the post-translational regulation and allosteric regulation of pyruvate dehydrogenase and carboxylase to maintain and support the partition of pyruvate synthesis and degradation.

Excerpted from Wikipedia’s “coenzyme A” article, available under the CC BY-SA 4.0 licence.