ChemFOnt: Showing chemical card for Homocitric acid (CFc000001908)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:46:39 UTC

Chemfont ID

CFc000001908

Molecule Identification

Common Name

Homocitric acid

Definition

Homocitric 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(R)-2-Hydroxy-1,2,4-butanetricarboxylic acid	ChEBI
(R)-2-Hydroxybutane-1,2,4-tricarboxylic acid	ChEBI
(R)-Homocitric acid	ChEBI
3-Hydroxy-3-carboxyadipic acid	ChEBI
Homocitrate	ChEBI
(R)-2-Hydroxy-1,2,4-butanetricarboxylate	Generator
(R)-2-Hydroxybutane-1,2,4-tricarboxylate	Generator
(R)-Homocitrate	Generator
3-Hydroxy-3-carboxyadipate	Generator
2-Hydroxybutane-1,2,4-tricarboxylate	HMDB
(2R)-2-Hydroxy-1,2,4-butanetricarboxylate	HMDB
(2R)-2-Hydroxy-1,2,4-butanetricarboxylic acid	HMDB
(±)-homocitrate	HMDB
(±)-homocitric acid	HMDB
2-Hydroxy-1,2,4-butanetricarboxylate	HMDB
2-Hydroxy-1,2,4-butanetricarboxylic acid	HMDB
Homocitric acid	HMDB

Chemical Formula

C₇H₁₀O₇

Average Molecular Weight

206.1501

Monoisotopic Molecular Weight

206.042652674

IUPAC Name

(2R)-2-hydroxybutane-1,2,4-tricarboxylic acid

Traditional Name

(R)-homocitric acid

CAS Registry Number

13052-73-8

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 Key

XKJVEVRQMLKSMO-SSDOTTSWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Hydroxy acid
Alpha-hydroxy acid
Tertiary alcohol
Carboxylic acid
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

homocitric acid (CHEBI:52222 )

Functional Ontology

Not Available

Placenta (HMDB: HMDB0003518)

Excreta

Biofluid or Excreta

Feces (PMID: 27543620)

Cellular substructure

Cytoplasm (HMDB: HMDB0003518)

Source

Endogenous

Endogenous (HMDB: HMDB0003518)

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Pyruvate Metabolism (PathBank: SMP0002355)
Lysine Metabolism (PathBank: SMP0002337)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	191 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-1	ChemAxon
logS	-0.03	ALOGPS
pKa (Strongest Acidic)	3.09	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	40.38 m³·mol⁻¹	ChemAxon
Polarizability	17.44 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon