Np mrd loader

You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on NP-MRD.
Record Information
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:39:50 UTC
NP-MRD IDNP0000073
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsovaleric acid
DescriptionIsovaleric 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 ). Isovaleric acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism.
3-Methyl-N-butyric acidChEBI
3-Methylbutanoic acidChEBI
3-Methylbutyric acidChEBI
beta-Methylbutyric acidChEBI
Delphinic acidChEBI
Isobutylformic acidChEBI
Isopentanoic acidChEBI
Isopropylacetic acidChEBI
Isovalerianic acidChEBI
b-Methylbutyric acidGenerator
Β-methylbutyric acidGenerator
3-Methyl butyric acidHMDB
3-Methylbutyric acid: isopropyl-acetateHMDB
3-Methylbutyric acid: isopropyl-acetic acidHMDB
3-Methyl-1-butanoic acidHMDB
Isovaleric acidKEGG
Chemical FormulaC5H10O2
Average Mass102.1317 Da
Monoisotopic Mass102.06808 Da
IUPAC Name3-methylbutanoic acid
Traditional Nameisovaleric acid
CAS Registry Number503-74-2
InChI Identifier
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-07-25View Spectrum
Species of Origin
Species NameSourceReference
Achillea millefoliumKNApSAcK Database
Anas platyrhynchosFooDB
Anser anserFooDB
Apium graveolensFooDB
Arctium lappaKNApSAcK Database
Artemisia carvifoliaLOTUS Database
Artemisia jacuticaLOTUS Database
Artemisia macrocephalaLOTUS Database
Bison bisonFooDB
Blattella germanicaLOTUS Database
Blepharocalyx salicifoliusLOTUS Database
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
Capsicum annuumFooDB
Capsicum annuum var. annuumFooDB
Carthamus tinctoriusKNApSAcK Database
Centaurea orientalisKNApSAcK Database
Centranthus macrosiphonLOTUS Database
Cervus canadensisFooDB
Cinnamomum aromaticumFooDB
Coffea arabicaKNApSAcK Database
Coffea arabica L.Plant
Croton megalobotrysLOTUS Database
Curio articulatusLOTUS Database
Cymbopogon citratusFooDB
Delphinus delphis-
Dromaius novaehollandiaeFooDB
Elsholtzia ciliataKNApSAcK Database
Equus caballusFooDB
Euonymus japonicusKNApSAcK Database
Fragaria x ananassaLOTUS Database
Gallus gallusFooDB
Glycine maxFooDB
Goupia glabraLOTUS Database
Homo sapiensLOTUS Database
Humulus lupulusKNApSAcK Database
Lagopus mutaFooDB
Lepus timidusFooDB
Levisticum officinaleFooDB
Lithospermum erythrorhizonKNApSAcK Database
Litsea cubebaKNApSAcK Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mentha arvensisFooDB
Mentha x piperitaFooDB
Micromelum minutumPlant
Morus albaKNApSAcK Database
Musa x paradisiacaFooDB
Nardostachys chinensisKNApSAcK Database
Nardostachys jatamansiPlant
Nicotiana tabacumKNApSAcK Database
Numida meleagrisFooDB
Ovis ariesFooDB
Pelargonium graveolensLOTUS Database
Phasianus colchicusFooDB
Piper nigrum L.FooDB
Pittosporum undulatumLOTUS Database
Plantago lanceolataPlant
Polygala senegaLOTUS Database
Prunus cerasusFooDB
Prunus domesticaLOTUS Database
Prunus persicaFooDB
Rubus idaeusFooDB
Saxifraga stoloniferaLOTUS Database
Saxifraga stolonifera Meerb.KNApSAcK Database
Solanum lycopersicumKNApSAcK Database
Solanum pennelliiLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Thamnophis butleriLOTUS Database
Trypanosoma bruceiLOTUS Database
Vaccinium angustifoliumLOTUS Database
Valeriana celticaLOTUS Database
Valeriana officinalisKNApSAcK Database
Valeriana spp.KNApSAcK Database
Viburnum prunifoliumLOTUS Database
Vitis viniferaLOTUS Database
Xanthium strumariumLOTUS Database
Species Where Detected
Species NameSourceReference
Homo sapiens (Skin microbiota)KNApSAcK Database
Homo sapiens (Skin)KNApSAcK Database
Staphylococcus aureusKNApSAcK Database
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
  • 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 FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
Experimental Properties
Melting Point-29.3 °CNot Available
Boiling Point175.00 to 177.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility40.7 mg/mLNot Available
LogP1.16Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
Water Solubility64.9 g/LALOGPS
pKa (Strongest Acidic)5.01ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity26.42 m³·mol⁻¹ChemAxon
Polarizability10.99 ųChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
DrugBank IDDB03750
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001324
KNApSAcK IDC00001189
Chemspider ID10001
KEGG Compound IDC08262
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-Methylbutanoic acid
PubChem Compound10430
PDB IDNot Available
ChEBI ID28484
Good Scents IDrw1056411
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Ackman RG: Birthweights in the Faroe Islands: possible role of isovaleric acid. J Intern Med. 1989 Feb;225(2):73-5. [PubMed:2646392 ]