Human Metabolome Database: Showing metabocard for Isovaleric acid (HMDB00718)

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

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

Record Information

Version

3.6

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2017-03-02 21:26:07 UTC

HMDB ID

HMDB00718

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Isovaleric acid

Description

Isovaleric acid, is a natural fatty acid found in a wide variety of plants and essential oils. Isovaleric acid is clear colorless liquid that is sparingly soluble in water, but well soluble in most common organic solvents. It has been suggested that isovaleric acid from pilot whales, a species frequently consumed in the Faroe Islands, may be the unusual dietary factor in prolonged gestation in the population of the Faroe Islands. Previous studies suggested that was due to the high intake of n-3 polyunsaturated fatty acids has been, but fatty acid data for eicosapentaenoic acid (EPA) and docosahexanoic acid (DHA) in blood lipids of Faroese and Norwegians was reviewed in terms of the type of fish eaten (mostly lean white fish with DHA much greater than EPA); the popular lean fish, thus, probably provides too little EPA to produce a marked effect on human biochemistry. (PMID 2646392 ).

Structure

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

Synonyms

Value	Source
3-Methyl-N-butyric acid	ChEBI
3-Methylbutanoic acid	ChEBI
3-Methylbuttersaeure	ChEBI
3-Methylbutyric acid	ChEBI
beta-Methylbutyric acid	ChEBI
Delphinic acid	ChEBI
Isobutylformic acid	ChEBI
Isopentanoic acid	ChEBI
Isopropylacetic acid	ChEBI
Isovalerate	ChEBI
Isovalerianic acid	ChEBI
Isovaleriansaeure	ChEBI
3-Methyl-N-butyrate	Generator
3-Methylbutanoate	Generator
3-Methylbutyrate	Generator
b-Methylbutyrate	Generator
b-Methylbutyric acid	Generator
beta-Methylbutyrate	Generator
β-methylbutyrate	Generator
β-methylbutyric acid	Generator
Delphinate	Generator
Isobutylformate	Generator
Isopentanoate	Generator
Isopropylacetate	Generator
Isovalerianate	Generator
3-Methyl butyric acid	HMDB
3-Methylbutyric acid: isopropyl-acetate	HMDB
3-Methylbutyric acid: isopropyl-acetic acid	HMDB

Chemical Formula

C₅H₁₀O₂

Average Molecular Weight

102.1317

Monoisotopic Molecular Weight

102.068079564

IUPAC Name

3-methylbutanoic acid

Traditional Name

isovaleric acid

CAS Registry Number

503-74-2

SMILES

CC(C)CC(O)=O

InChI Identifier

InChI=1S/C5H10O2/c1-4(2)3-5(6)7/h4H,3H2,1-2H3,(H,6,7)

InChI Key

GWYFCOCPABKNJV-UHFFFAOYSA-N

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Methyl-branched fatty acids

Alternative Parents

Substituents

Methyl-branched fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

branched-chain saturated fatty acid (CHEBI:28484 )
short-chain fatty acid (CHEBI:28484 )
methylbutyric acid (CHEBI:28484 )
Branched fatty acids (C08262 )
Branched fatty acids (LMFA01020181 )

Ontology

Status

Detected and 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

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-29.3 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	40.7 mg/mL	Not Available
LogP	1.16	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	64.9 mg/mL	ALOGPS
logP	1.26	ALOGPS
logP	1.21	ChemAxon
logS	-0.2	ALOGPS
pKa (Strongest Acidic)	5.01	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	26.42 m³·mol^-1	ChemAxon
Polarizability	10.99 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
GC-MS	GC-MS Spectrum - EI-B	splash10-03dl-9000000000-9e19eb5f5137b78591df	View in MoNA
GC-MS	GC-MS Spectrum - EI-B	splash10-03dl-9000000000-43967f1315b6b575f330	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0gvo-9300000000-16b5d15d26810b72bb36	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-692791435c37fa74a692	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-b4c1b59653cd4d803637	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-03dl-9000000000-b0f7e399edb7f95572ed	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-03dl-9000000000-c8be68873f336c8de6d6	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0900000000-d0f20bc9813dcba79e8b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-0900000000-63b09019c280c88ee64d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0udi-1900000000-ef9ee29c1febd59e6a00	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9200000000-e825f0aa9ab54c1695d3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-9000000000-9ba126f982634fdc9406	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-afb863a56c8763c30251	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-8900000000-244535e4070d536a29b3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pc0-9300000000-93ed2bc326380cb0d880	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-44b2fa11a5a6daab8dd0	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-03dl-9000000000-e7c77b2bc7f3ac5191e9	View in MoNA
1D NMR	13C NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
1D NMR	1H NMR Spectrum	Not Available
1D NMR	13C NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Location

Not Available

Pathways

Not Available

Normal Concentrations

Biofluid	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	1.6 (0.3-2.7) uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Cerebrospinal Fluid (CSF)	Detected and Quantified	1.35 (0-2.7) uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Feces	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Both	Normal	23454028	details
Feces	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Both	Normal	21761941	details
Feces	Detected but not Quantified	Not Applicable	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Applicable	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected and Quantified	1622.807 +/- 672.465 uM	Not Specified	Not Specified	Normal	19573517	details
Feces	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Both	Normal	20055983	details
Feces	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Both	Normal	18085514	details
Feces	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Both	Normal	18085514	details
Feces	Detected and Quantified	1280 +/- 920 nmol/g of feces	Adult (>18 years old)	Female	Normal	23997757	details
Feces	Detected and Quantified	0 - 28.65 ppm	Children (1-13 years old)	Not Specified	Normal	21970810	details
Feces	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Both	Normal	17314143	details
Feces	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Both	Normal	25670064	details
Feces	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Both	Normal	23940645	details
Saliva	Detected and Quantified	54.03 +/- 39.40 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected and Quantified	3.415 +/- 0.858 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Mordechai, Hien, ...	details
Urine	Detected and Quantified	1.4 (0.8-2.5) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	41.0 +/- 25.0 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	0.42 ± 0.02 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	17374376	details
Urine	Detected and Quantified	0.07 (0.0-0.13) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	3.5 (1.1-6.7) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	Geigy Scientific ...	details

Abnormal Concentrations

Biofluid	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Both	Irritable bowel syndrome	21761941	details
Feces	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Both	Ulcerative colitis	21761941	details
Feces	Detected and Quantified	0 - 53.24 ppm	Children (1-13 years old)	Not Specified	Treated celiac disease	21970810	details
Feces	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Both	Campylobacter jejuni infection	17314143	details
Feces	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Both	Clostridium difficile infection	17314143	details
Feces	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Both	Ulcerative Colitis	17314143	details
Feces	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Both	Colorectal cancer	23940645	details
Feces	Detected but not Quantified	Not Applicable	Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	details
Urine	Detected and Quantified	2.559 +/- 2.305 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Mordechai, Hien, ...	details

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB03750

DrugBank Metabolite ID

Not Available

Phenol Explorer Compound ID

Not Available

Phenol Explorer Metabolite ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

NuGOwiki Link

Metagene Link

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

References

Synthesis Reference

Imada, Yukio; Mizuno, Sumiko; Mikawa, Takashi. Manufacture of isovaleric acid and 2-methylbutyric acid. Jpn. Kokai Tokkyo Koho (1986), 3 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Silva MF, Selhorst J, Overmars H, van Gennip AH, Maya M, Wanders RJ, de Almeida IT, Duran M: Characterization of plasma acylcarnitines in patients under valproate monotherapy using ESI-MS/MS. Clin Biochem. 2001 Nov;34(8):635-8. [PubMed:11849623 ]
Hoffmann GF, von Kries R, Klose D, Lindner M, Schulze A, Muntau AC, Roschinger W, Liebl B, Mayatepek E, Roscher AA: Frequencies of inherited organic acidurias and disorders of mitochondrial fatty acid transport and oxidation in Germany. Eur J Pediatr. 2004 Feb;163(2):76-80. Epub 2004 Jan 9. [PubMed:14714182 ]
Arthur K, Hommes FA: Simple isotope dilution assay for propionic acid and isovaleric acid. J Chromatogr B Biomed Appl. 1995 Nov 3;673(1):132-5. [PubMed:8925066 ]
Ara K, Hama M, Akiba S, Koike K, Okisaka K, Hagura T, Kamiya T, Tomita F: Foot odor due to microbial metabolism and its control. Can J Microbiol. 2006 Apr;52(4):357-64. [PubMed:16699586 ]
Ackman RG: Birthweights in the Faroe Islands: possible role of isovaleric acid. J Intern Med. 1989 Feb;225(2):73-5. [PubMed:2646392 ]

Showing metabocard for Isovaleric acid (HMDB00718)

Structure for HMDB00718 (Isovaleric acid)