Ketopantoic acid

Ketopantoic acid is the organic compound with the formula HOCH₂(CH₃)₂CC(O)CO₂H. At physiological conditions, ketopantoic acid exists as its conjugate base, ketopantoate (HOCH₂(CH₃)₂CC(O)CO₂⁻).

Ketopantoic acid

Names
Other names 4-Hydroxy-3,3-dimethyl-2-oxobutanoic acid; 2-Dehydropantoic acid
Identifiers
CAS Number	470-30-4
3D model (JSmol)	Interactive image
Beilstein Reference	2242422
ChEBI	CHEBI:17094
ChemSpider	37
DrugBank	DB03795
KEGG	C00966
PubChem CID	38
CompTox Dashboard (EPA)	DTXSID90274258
InChI InChI=1S/C6H10O4/c1-6(2,3-7)4(8)5(9)10/h7H,3H2,1-2H3,(H,9,10) Key: PKVVTUWHANFMQC-UHFFFAOYSA-N
SMILES CC(C)(CO)C(=O)C(=O)O
Properties
Chemical formula	C6H10O4
Molar mass	146.142 g·mol−1
Appearance	colorless or white
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Biosynthetic context

Its biosynthesis proceeds from ketoisovalerate by hydroxymethylation:

(CH₃)₂CHC(O)CO₂⁻ + CH₂O → HOCH₂(CH₃)₂CC(O)CO₂⁻

This conversion is catalyzed by ketopantoate hydroxymethyltransferase, which gives ketopantoate.

Ketopantoate is substrate for 2-dehydropantoate 2-reductase,^[1] which produces pantoate, a precursor to pantothenic acid, a common prosthetic group.^[2]