Showing Compound Homocitric acid (FDB023186)

Record Information

Version

1.0

Creation date

2011-09-21 00:25:55 UTC

Update date

2015-07-21 06:57:35 UTC

Primary ID

FDB023186

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Homocitric acid

Description

Homocitric acid 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 a-ketoglutarate with acetyl coenzyme A and propionyl coenzyme A). (PMID: 7850997) [HMDB]

CAS Number

3562-74-1

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Search:

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

Showing 1 to 10 of 17 entries

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

Chemical Formula

C7H10O7

IUPAC name

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

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

Isomeric SMILES

OC(=O)CC[C@@](O)(CC(O)=O)C(O)=O

Average Molecular Weight

206.1501

Monoisotopic Molecular Weight

206.042652674

Classification

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 )

Ontology

Disposition

Biological location:

Subcellular:

Cytoplasm

Source:

Endogenous

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Homocitric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fsr-2900000000-1b6221744212821d13a4	Spectrum
Predicted GC-MS	Homocitric acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004i-6039700000-bbcdc859874cb31d16db	Spectrum
Predicted GC-MS	Homocitric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Homocitric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06ya-0910000000-10ce2a6c7dde8f6414f9	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03kc-6900000000-cc774f0962c580270a86	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-3900000000-1dbf32a3d216327d832a	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-08fr-1910000000-24186d115834b7a98219	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-07vi-3900000000-78ce979f1c8cb053a6d2	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0aor-9600000000-dc1759e8907b4db138bd	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-07wl-1910000000-93d90a9e9b47624dde71	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-014r-2900000000-10b9bd64cc7e5be41000	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00ku-9800000000-3926d2bdbaae25830936	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052u-0930000000-b304c640e74bcbd68b82	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9200000000-f4181d391bb21114c3e1	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9200000000-28608fc4dea9afb51354	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

388564

ChEMBL ID

Not Available

KEGG Compound ID

C01251

Pubchem Compound ID

439459

Pubchem Substance ID

Not Available

ChEBI ID

17852

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB03518

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

HCA

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Homocitrate

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

Showing Compound Homocitric acid (FDB023186)

Structure for FDB023186 (Homocitric acid)