Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:27:22 UTC
Update Date2024-04-30 19:54:59 UTC
Metabolite IDMMDBc0032919
Metabolite Identification
Common Name(2R)-Homocitric acid
DescriptionHomocitric acid (CAS: 3562-74-1) is a normal urinary organic acid (PMID: 14708889 ). Homocitric acid is a citric acid analogue found as a minor metabolite in urine samples from patients with propionic acidaemia. Homocitric acid is formed by citrate synthase due to propionyl-CoA carboxylase deficiency (by the citrate synthase condensation reaction of alpha-ketoglutarate with acetyl coenzyme A and propionyl coenzyme A) (PMID: 7850997 ). Homocitric acid has been identified in the human placenta (PMID: 32033212 ).
Structure
Synonyms
ValueSource
(R)-2-Hydroxy-1,2,4-butanetricarboxylic acidChEBI
(R)-2-Hydroxybutane-1,2,4-tricarboxylic acidChEBI
(R)-Homocitric acidChEBI
3-Hydroxy-3-carboxyadipic acidChEBI
HomocitrateChEBI
(R)-2-Hydroxy-1,2,4-butanetricarboxylateGenerator
(R)-2-Hydroxybutane-1,2,4-tricarboxylateGenerator
(R)-HomocitrateGenerator
3-Hydroxy-3-carboxyadipateGenerator
2-Hydroxybutane-1,2,4-tricarboxylateHMDB
(2R)-2-Hydroxy-1,2,4-butanetricarboxylateHMDB
(2R)-2-Hydroxy-1,2,4-butanetricarboxylic acidHMDB
(±)-homocitrateHMDB
(±)-homocitric acidHMDB
2-Hydroxy-1,2,4-butanetricarboxylateHMDB
2-Hydroxy-1,2,4-butanetricarboxylic acidHMDB
Homocitric acidHMDB
Molecular FormulaC7H10O7
Average Mass206.1501
Monoisotopic Mass206.042652674
IUPAC Name(2R)-2-hydroxybutane-1,2,4-tricarboxylic acid
Traditional Name(R)-homocitric acid
CAS Registry Number3562-74-1
SMILES
OC(=O)CC[C@@](O)(CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C7H10O7/c8-4(9)1-2-7(14,6(12)13)3-5(10)11/h14H,1-3H2,(H,8,9)(H,10,11)(H,12,13)/t7-/m1/s1
InChI KeyXKJVEVRQMLKSMO-SSDOTTSWSA-N