Livestock Metabolome Database: Showing metabocard for Isovaleric acid (LMDB00228)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:45:11 UTC

Update Date

2016-09-23 18:44:57 UTC

Lmdb

LMDB00228

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 animal biochemistry. (PMID 2646392 ).

Structure

MOL SDF PDB SMILES InChI

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
3-Methyl-1-butanoic acid	HMDB
Isovaleric acid	KEGG

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

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

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

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
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	Yes	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	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dl-9000000000-9e19eb5f5137b78591df	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dl-9000000000-43967f1315b6b575f330	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dl-9000000000-9e19eb5f5137b78591df	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03dl-9000000000-43967f1315b6b575f330	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052f-9000000000-2825512cee017b3ab87c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-059f-9200000000-628e11f1ffbaa913ef57	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0gvo-9300000000-16b5d15d26810b72bb36	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-692791435c37fa74a692	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-b4c1b59653cd4d803637	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positive	splash10-03dl-9000000000-b0f7e399edb7f95572ed	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-03dl-9000000000-c8be68873f336c8de6d6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0udi-0900000000-d0f20bc9813dcba79e8b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0udi-0900000000-63b09019c280c88ee64d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0udi-1900000000-ef9ee29c1febd59e6a00	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-d0f20bc9813dcba79e8b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-0900000000-63b09019c280c88ee64d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0udi-1900000000-ef9ee29c1febd59e6a00	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-014i-9000000000-871b21c20bba686fb915	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-1900000000-6ce72c7a41bfb4bc1b2d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-0nmi-9300000000-efcb74e7796ba9769f97	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-9200000000-e825f0aa9ab54c1695d3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-9000000000-9ba126f982634fdc9406	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-afb863a56c8763c30251	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0zfr-8900000000-244535e4070d536a29b3	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0pc0-9300000000-93ed2bc326380cb0d880	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-44b2fa11a5a6daab8dd0	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000f-9000000000-f59a47a684453302cbed	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-83176e54a19e36af76f2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-81052c8b00621fcf0443	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-4c159e60dacc58e6ba98	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ue9-7900000000-fd28737d49ed09628cfa	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03dl-9000000000-e7c77b2bc7f3ac5191e9	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Feces
Ruminal Fluid
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Feces	Detected but not Quantified	Not Applicable	Not Available	Equine	E. E. Escalona, J...	details
Ruminal Fluid	Detected and Quantified	4800 uM	Not Available	Ovine	M.L.K. Bonsi, P.O...	details
Ruminal Fluid	Detected and Quantified	4400-4700 uM	Not Available	Ovine	M.L.K. Bonsi, P.O...	details
Ruminal Fluid	Detected and Quantified	5700-7200 uM	Not Available	Ovine	M.L.K. Bonsi, P.O...	details
Ruminal Fluid	Detected and Quantified	720 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	891 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	932 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	998 uM	Not Available	Bovine	Burim NA, Qendrim...	details
Ruminal Fluid	Detected and Quantified	900 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	1080 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	1090 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	1130 uM	Not Available	Bovine	22959937	details
Ruminal Fluid	Detected and Quantified	1,094 +/- 207 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	1,094 +/- 207 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	1,133 +/- 192 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	1,180 +/- 420 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	805 +/- 121 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	900 +/- 140 uM	Not Available	Bovine	Saleem F, Bouatra...	details
Ruminal Fluid	Detected and Quantified	533 +/- 82 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	681 +/- 120 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	726 +/- 99 uM	Not Available	Bovine	22706048	details
Ruminal Fluid	Detected and Quantified	490 uM	Not Available	Caprine	25471302	details
Ruminal Fluid	Detected and Quantified	620 uM	Not Available	Caprine	25471302	details
Ruminal Fluid	Detected and Quantified	710 uM	Not Available	Caprine	25471302	details
Ruminal Fluid	Detected and Quantified	1,280 +/- 98 uM	Not Available	Caprine	22706048	details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	24617926	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Porcine	21761043	details