Human Metabolome Database: Showing metabocard for 4-Hydroxyisovaleric acid (HMDB0002011)

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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

4.0

Creation Date

2006-05-22 14:17:31 UTC

Update Date

2017-09-21 18:58:49 UTC

HMDB ID

HMDB0002011

Secondary Accession Numbers

HMDB02011

Metabolite Identification

Common Name

4-Hydroxyisovaleric acid

Description

4-hydroxyisovaleric acid is a metabolite of isovaleric acid that has been reported to be found in the urine of patients with isovaleric acidemia. It seems to be an intermediate product in the formation of methylsuccinic acid from isovaleric acid by omega-. oxidation.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
4-Hydroxyisopentanoate	HMDB
4-Hydroxyisopentanoic acid	HMDB
4-Hydroxyisovalerate	HMDB

Chemical Formula

C₅H₁₀O₃

Average Molecular Weight

118.1311

Monoisotopic Molecular Weight

118.062994186

IUPAC Name

4-hydroxy-3-methylbutanoic acid

Traditional Name

4-hydroxyisopentanoate

CAS Registry Number

77220-86-1

SMILES

CC(CO)CC(O)=O

InChI Identifier

InChI=1S/C5H10O3/c1-4(3-6)2-5(7)8/h4,6H,2-3H2,1H3,(H,7,8)

InChI Key

ZGYGEPZZMAXSKH-UHFFFAOYSA-N

Chemical Taxonomy

Description

This compound belongs to the class of chemical entities known as hydroxy fatty acids. These are fatty acids in which the chain bears a hydroxyl group.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Lipids and lipid-like molecules

Sub Class

Fatty Acyls

Direct Parent

Hydroxy fatty acids

Alternative Parents

Substituents

Methyl-branched fatty acid
Short-chain hydroxy acid
Hydroxy fatty acid
Branched fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Hydroxy fatty acids (LMFA01050399 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Food

Biofunction

Cell signaling
Fuel and energy storage
Fuel or energy source
Membrane integrity/stability

Application

Nutrients
Stabilizers
Surfactants and Emulsifiers

Cellular locations

Extracellular
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	276.0 mg/mL	ALOGPS
logP	-0.09	ALOGPS
logP	-0.15	ChemAxon
logS	0.37	ALOGPS
pKa (Strongest Acidic)	4.59	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	28.27 m³·mol^-1	ChemAxon
Polarizability	11.91 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Blood
Urine

Tissue Location

Not Available

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

No entries found

Normal Concentrations

Biofluid	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified		Not Available	Not Available	Normal		details

Abnormal Concentrations

Biofluid	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified		Not Available	Not Available	Isovaleric acidemia	11978597	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

DrugBank Metabolite ID

Not Available

Phenol Explorer Compound ID

Not Available

Phenol Explorer Metabolite ID

Not Available

FoodDB ID

FDB022793

KNApSAcK ID

Not Available

Chemspider ID

116413

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

NuGOwiki Link

HMDB0002011

METLIN ID

6434

PubChem Compound

131760

PDB ID

Not Available

ChEBI ID

384411

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Truscott RJ, Malegan D, McCairns E, Burke D, Hick L, Sims P, Halpern B, Tanaka K, Sweetman L, Nyhan WL, Hammond J, Bumack C, Haan EA, Danks DM: New metabolites in isovaleric acidemia. Clin Chim Acta. 1981 Mar 5;110(2-3):187-203. [PubMed:6452974 ]

Showing metabocard for 4-Hydroxyisovaleric acid (HMDB0002011)

Structure for HMDB0002011 (4-Hydroxyisovaleric acid)