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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 17:47:25 UTC
Update Date2019-07-23 06:10:11 UTC
HMDB IDHMDB0032042
Secondary Accession Numbers
  • HMDB32042
Metabolite Identification
Common NameButyl 3-methylbutanoate
DescriptionButyl 3-methylbutanoate is found in alcoholic beverages. Butyl 3-methylbutanoate is used in fruit flavouring. Butyl 3-methylbutanoate is present in apricot, banana, strawberries, Parmesan and gruyere de comte cheeses, white wine, olives, plums, jack fruit, cherimoga and lamb's lettuc
Structure
Data?1563862211
Synonyms
ValueSource
1-Butyl isovalerateHMDB
Butanoic acid, 3-methyl-, butyl esterHMDB
Butyl 3-methylbutyrateHMDB
Butyl isopentanoateHMDB
Butyl isovalerateHMDB
Butyl isovalerianateHMDB
FEMA 2218HMDB
N-Butyl 3-methylbutanoateHMDB
N-Butyl isopentanoateHMDB
N-Butyl isovalerateHMDB
Chemical FormulaC9H18O2
Average Molecular Weight158.238
Monoisotopic Molecular Weight158.13067982
IUPAC Namebutyl 3-methylbutanoate
Traditional Namebutyl isovalerate
CAS Registry Number109-19-3
SMILES
CCCCOC(=O)CC(C)C
InChI Identifier
InChI=1S/C9H18O2/c1-4-5-6-11-9(10)7-8(2)3/h8H,4-7H2,1-3H3
InChI KeyAYWJSCLAAPJZEF-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acid esters
Direct ParentFatty acid esters
Alternative Parents
Substituents
  • Fatty acid ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.58 g/LALOGPS
logP3.15ALOGPS
logP2.68ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity45.06 m³·mol⁻¹ChemAxon
Polarizability19.11 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4u-9000000000-8dd1d91769ff865eda84JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4u-9000000000-8dd1d91769ff865eda84JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4r-9000000000-d17977361e54b8e87f0fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-7900000000-56a693e9b0e01cb69a7dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-ed0591535377a7fcae4eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-8b87a907dc105a162036JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a59-8900000000-d73b5432a01d094413aaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc0-9500000000-8c1b5d82216ce8322121JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a59-9100000000-fba64091fe32ab005fe0JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected and Quantified63.196 (0-358.110) nmol/g wet fecesChildren (1 - 13 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected and Quantified63.196 nmol/g wet fecesAdult (>18 years old)Both
Immunoglobulin A nephropathy
details
FecesDetected and Quantified84.261 nmol/g wet fecesAdult (>18 years old)Both
Immunoglobulin A nephropathy
details
FecesDetected and Quantified84.261 (0-400.241) nmol/g wet fecesChildren (1 - 13 years old)Both
Autism
details
FecesDetected and Quantified84.261 (0-315.980) nmol/g wet fecesChildren (1 - 13 years old)Both
Developmental Disorder Not Otherwise Specified
details
FecesDetected but not Quantified Adult (>18 years old)Both
Diarrhea-predominant IBS
details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Diarrhoea predominant irritable bowel syndrome
  1. Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
Immunoglobulin A nephropathy
  1. De Angelis M, Montemurno E, Piccolo M, Vannini L, Lauriero G, Maranzano V, Gozzi G, Serrazanetti D, Dalfino G, Gobbetti M, Gesualdo L: Microbiota and metabolome associated with immunoglobulin A nephropathy (IgAN). PLoS One. 2014 Jun 12;9(6):e99006. doi: 10.1371/journal.pone.0099006. eCollection 2014. [PubMed:24922509 ]
Autism
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Pervasive developmental disorder not otherwise specified
  1. De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB008746
KNApSAcK IDNot Available
Chemspider ID7693
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound7981
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.