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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:34:17 UTC
Update Date2022-03-07 02:52:24 UTC
HMDB IDHMDB0030028
Secondary Accession Numbers
  • HMDB30028
Metabolite Identification
Common NameEthyl isovalerate
DescriptionEthyl isovalerate, also known as ethyl isopentanoate or fema 2463, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acids. Ethyl isovalerate is a very hydrophobic molecule, practically insoluble in water, and relatively neutral.
Structure
Data?1563861926
Synonyms
ValueSource
Ethyl 3-methylbutyrateChEBI
Ethyl beta-methylbutyrateChEBI
Ethyl isopentanoateChEBI
Ethyl 3-methylbutyric acidGenerator
Ethyl b-methylbutyrateGenerator
Ethyl b-methylbutyric acidGenerator
Ethyl beta-methylbutyric acidGenerator
Ethyl β-methylbutyrateGenerator
Ethyl β-methylbutyric acidGenerator
Ethyl isopentanoic acidGenerator
Ethyl isovaleric acidGenerator
3-Methylbutanoic acid ethyl esterHMDB
3-Methylbutyric acid ethyl esterHMDB
Butyric acid, 3-methyl-, ethyl ester (6ci,7ci,8ci)HMDB
Ethyl 3-methylbutanoateHMDB
Ethyl iso-pentanoateHMDB
Ethyl isovalerianateHMDB
EthylisovalerateHMDB
FEMA 2463HMDB
Isovaleric acid, ethyl esterHMDB
Ethyl 3-methyl-butanoic acidGenerator
Ethyl isovalerateMeSH
Ethyl 3-methyl butanoic acidGenerator
Chemical FormulaC7H14O2
Average Molecular Weight130.1849
Monoisotopic Molecular Weight130.099379692
IUPAC Nameethyl 3-methylbutanoate
Traditional Nameethyl isovalerate
CAS Registry Number108-64-5
SMILES
CCOC(=O)CC(C)C
InChI Identifier
InChI=1S/C7H14O2/c1-4-9-7(8)5-6(2)3/h6H,4-5H2,1-3H3
InChI KeyPPXUHEORWJQRHJ-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point-99.3 °CNot Available
Boiling Point131.00 to 133.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2 mg/mL at 20 °CNot Available
LogP2.158 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.05 g/LALOGPS
logP2.21ALOGPS
logP1.71ChemAxon
logS-1.5ALOGPS
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity35.94 m³·mol⁻¹ChemAxon
Polarizability14.99 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+129.13331661259
DarkChem[M-H]-125.6631661259
DeepCCS[M+H]+134.27430932474
DeepCCS[M-H]-131.7530932474
DeepCCS[M-2H]-168.15130932474
DeepCCS[M+Na]+143.31830932474
AllCCS[M+H]+130.932859911
AllCCS[M+H-H2O]+126.832859911
AllCCS[M+NH4]+134.732859911
AllCCS[M+Na]+135.832859911
AllCCS[M-H]-132.132859911
AllCCS[M+Na-2H]-135.032859911
AllCCS[M+HCOO]-138.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ethyl isovalerateCCOC(=O)CC(C)C1050.8Standard polar33892256
Ethyl isovalerateCCOC(=O)CC(C)C844.0Standard non polar33892256
Ethyl isovalerateCCOC(=O)CC(C)C867.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Ethyl isovalerate EI-B (Non-derivatized)splash10-000i-9000000000-131dee797c5fc67efffb2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl isovalerate EI-B (Non-derivatized)splash10-002r-9000000000-2e5a458a237911c47c6a2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl isovalerate EI-B (Non-derivatized)splash10-000i-9000000000-131dee797c5fc67efffb2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Ethyl isovalerate EI-B (Non-derivatized)splash10-002r-9000000000-2e5a458a237911c47c6a2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl isovalerate GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a73-9000000000-c1b7378681f97f4f6e002016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ethyl isovalerate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0550-9000000000-fe91c2131284961ab91b2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isovalerate 10V, Positive-QTOFsplash10-001i-6900000000-8ba1d1c1f966ad17dca52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isovalerate 20V, Positive-QTOFsplash10-0007-9100000000-eed32a90ffaed5691eae2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isovalerate 40V, Positive-QTOFsplash10-052f-9000000000-4aa67dd97a013a36b6992016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isovalerate 10V, Negative-QTOFsplash10-0059-8900000000-e5224d86eecfb1c055672016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isovalerate 20V, Negative-QTOFsplash10-003r-9300000000-52d42ab52ca889399d3d2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isovalerate 40V, Negative-QTOFsplash10-0a5d-9000000000-9371873aec37f00341692016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isovalerate 10V, Positive-QTOFsplash10-052o-9100000000-766f5583c2402ffa0e2c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isovalerate 20V, Positive-QTOFsplash10-0006-9000000000-2aebc9e53f59ab2f71702021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isovalerate 40V, Positive-QTOFsplash10-0006-9000000000-60a8c2b40ca14ed3bcc82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isovalerate 10V, Negative-QTOFsplash10-004j-7900000000-83afa7944c4e41de10ad2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isovalerate 20V, Negative-QTOFsplash10-001i-9000000000-d45b079d526eaee5b5512021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ethyl isovalerate 40V, Negative-QTOFsplash10-00kf-9000000000-80702d1ca5b1addba3592021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-30Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothAutism details
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothPervasive Developmental Disorder Not Otherwise Specified details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothCrohns disease details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothUlcerative colitis details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Nonalcoholic fatty liver disease
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 ]
Crohn's disease
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Ulcerative colitis
  1. Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
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
FooDB IDFDB001326
KNApSAcK IDC00050449
Chemspider ID7657
KEGG Compound IDC12290
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEthyl isovalerate
METLIN IDNot Available
PubChem Compound7945
PDB IDNot Available
ChEBI ID31571
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1007041
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.