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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:49:09 UTC
Update Date2022-03-07 02:53:18 UTC
HMDB IDHMDB0032319
Secondary Accession Numbers
  • HMDB32319
Metabolite Identification
Common Namecis-3-Hexenyl crotonate
Descriptioncis-3-Hexenyl crotonate belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. Based on a literature review a small amount of articles have been published on cis-3-Hexenyl crotonate.
Structure
Data?1563862248
Synonyms
ValueSource
cis-3-Hexenyl crotonic acidGenerator
(3E)-3-Hexen-1-yl ester(2E)-2-butenoic acidHMDB
(3E)-3-Hexenyl ester(2E)-2-butenoic acidHMDB
(3Z)-3-Hexen-1-yl ester(2E)-2-butenoic acidHMDB
(3Z)-3-Hexenyl (2Z)-2-butenoateHMDB
(3Z)-3-Hexenyl ester(2E)-2-butenoic acidHMDB
(e)-3-Hexenyl crotonateHMDB
(Z)-3-Hexenyl (e)-2-butenoateHMDB
(Z)-3-Hexenyl crotonateHMDB
cis-3-Hexenyl trans-2-butenoateHMDB
Chemical FormulaC10H16O2
Average Molecular Weight168.2328
Monoisotopic Molecular Weight168.115029756
IUPAC Name(3Z)-hex-3-en-1-yl (2E)-but-2-enoate
Traditional Name(3Z)-hex-3-en-1-yl (2E)-but-2-enoate
CAS Registry Number65405-80-3
SMILES
CC\C=C/CCOC(=O)\C=C\C
InChI Identifier
InChI=1S/C10H16O2/c1-3-5-6-7-9-12-10(11)8-4-2/h4-6,8H,3,7,9H2,1-2H3/b6-5-,8-4+
InChI KeyKITGYVIOYOCIIE-QNMAEOQASA-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
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate 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 DescriptorsNot Available
Ontology
Physiological effect
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.11 g/LALOGPS
logP2.95ALOGPS
logP3.15ChemAxon
logS-3.2ALOGPS
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity51.93 m³·mol⁻¹ChemAxon
Polarizability19.35 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+141.87731661259
DarkChem[M-H]-137.43231661259
DeepCCS[M+H]+142.94230932474
DeepCCS[M-H]-139.49630932474
DeepCCS[M-2H]-176.77630932474
DeepCCS[M+Na]+152.23830932474
AllCCS[M+H]+141.832859911
AllCCS[M+H-H2O]+137.932859911
AllCCS[M+NH4]+145.432859911
AllCCS[M+Na]+146.532859911
AllCCS[M-H]-142.632859911
AllCCS[M+Na-2H]-144.432859911
AllCCS[M+HCOO]-146.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
cis-3-Hexenyl crotonateCC\C=C/CCOC(=O)\C=C\C1674.0Standard polar33892256
cis-3-Hexenyl crotonateCC\C=C/CCOC(=O)\C=C\C1218.3Standard non polar33892256
cis-3-Hexenyl crotonateCC\C=C/CCOC(=O)\C=C\C1283.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - cis-3-Hexenyl crotonate EI-B (Non-derivatized)splash10-014i-9000000000-c727e746c3c867f93a012017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - cis-3-Hexenyl crotonate EI-B (Non-derivatized)splash10-014i-9000000000-c727e746c3c867f93a012018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-3-Hexenyl crotonate GC-MS (Non-derivatized) - 70eV, Positivesplash10-014i-9000000000-6e03b536e82b58d3590d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - cis-3-Hexenyl crotonate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl crotonate 10V, Positive-QTOFsplash10-014i-7900000000-2291fc990c0972aa308b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl crotonate 20V, Positive-QTOFsplash10-00lr-9100000000-e5a8307ae04105f9b18c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl crotonate 40V, Positive-QTOFsplash10-0frx-9000000000-dce9f235edeb18a638dc2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl crotonate 10V, Negative-QTOFsplash10-014i-9700000000-b485ae3c24cdd1dc83362016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl crotonate 20V, Negative-QTOFsplash10-014r-9100000000-1d29fe73e0390deddeec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl crotonate 40V, Negative-QTOFsplash10-014u-9000000000-c0893a61f7bd827690d92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl crotonate 10V, Negative-QTOFsplash10-014i-9800000000-10769e75a966913e42602021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl crotonate 20V, Negative-QTOFsplash10-000i-9000000000-9a6a10dfecb6fcca78e52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl crotonate 40V, Negative-QTOFsplash10-00kf-9000000000-fc9809098983e5c3f63c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl crotonate 10V, Positive-QTOFsplash10-067i-9000000000-a88a872ba617fa0211742021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl crotonate 20V, Positive-QTOFsplash10-0api-9000000000-490ed30c6805f3a976852021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-3-Hexenyl crotonate 40V, Positive-QTOFsplash10-0ar3-9000000000-42a1694300cdc675a7a32021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB009569
KNApSAcK IDC00055584
Chemspider ID17347416
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16220110
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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. (). EAFUS: Everything Added to Food in the United States.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.