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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:27:12 UTC
Update Date2022-03-07 02:54:09 UTC
HMDB IDHMDB0034576
Secondary Accession Numbers
  • HMDB34576
Metabolite Identification
Common Name3-Acetoxyscirpene-4,15-diol
Description2-Hexenyl butanoate, also known as (e)-2-hexenyl butyrate or fema 3926, belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid. 2-Hexenyl butanoate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563862584
Synonyms
ValueSource
2-Hexenyl butanoic acidGenerator
(2E)-2-Hexenyl butyrateHMDB
(e)-2-Hexen-1-ol, butanoateHMDB
(e)-2-Hexenyl butanoateHMDB
(e)-2-Hexenyl butyrateHMDB
2-Hexenyl ester(Z)-butanoic acidHMDB
FEMA 3926HMDB
trans-2-Hexenyl butanoateHMDB
trans-2-Hexenyl butyrateHMDB
trans-2-Hexenyl N-butyrateHMDB
trans-2-HEXENYLBUTYRATEHMDB
(3-alpha,4-beta-)-3-Acetoxyscirpene-4,15-diolHMDB
11'-Hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-10'-yl acetic acidGenerator
Chemical FormulaC17H24O6
Average Molecular Weight324.3689
Monoisotopic Molecular Weight324.1572885
IUPAC Name11'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-10'-yl acetate
Traditional Name11'-hydroxy-2'-(hydroxymethyl)-1',5'-dimethyl-8'-oxaspiro[oxirane-2,12'-tricyclo[7.2.1.0²,⁷]dodecan]-5'-en-10'-yl acetate
CAS Registry Number70402-13-0
SMILES
CC(=O)OC1C(O)C2(C)C3(CO3)C1OC1C=C(C)CCC21CO
InChI Identifier
InChI=1S/C17H24O6/c1-9-4-5-16(7-18)11(6-9)23-14-12(22-10(2)19)13(20)15(16,3)17(14)8-21-17/h6,11-14,18,20H,4-5,7-8H2,1-3H3
InChI KeyNFFRTZSZVQIMDJ-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
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 Solubility4.41 g/LALOGPS
logP0.53ALOGPS
logP-0.064ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)13.51ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area88.52 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity79.95 m³·mol⁻¹ChemAxon
Polarizability33.44 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+174.42731661259
DarkChem[M-H]-167.31431661259
DeepCCS[M-2H]-204.01530932474
DeepCCS[M+Na]+179.26830932474
AllCCS[M+H]+176.732859911
AllCCS[M+H-H2O]+173.732859911
AllCCS[M+NH4]+179.532859911
AllCCS[M+Na]+180.232859911
AllCCS[M-H]-180.732859911
AllCCS[M+Na-2H]-180.732859911
AllCCS[M+HCOO]-180.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Acetoxyscirpene-4,15-diolCC(=O)OC1C(O)C2(C)C3(CO3)C1OC1C=C(C)CCC21CO3640.9Standard polar33892256
3-Acetoxyscirpene-4,15-diolCC(=O)OC1C(O)C2(C)C3(CO3)C1OC1C=C(C)CCC21CO2265.0Standard non polar33892256
3-Acetoxyscirpene-4,15-diolCC(=O)OC1C(O)C2(C)C3(CO3)C1OC1C=C(C)CCC21CO2404.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Acetoxyscirpene-4,15-diol,1TMS,isomer #1CC(=O)OC1C2OC3C=C(C)CCC3(CO)C(C)(C1O[Si](C)(C)C)C21CO12437.5Semi standard non polar33892256
3-Acetoxyscirpene-4,15-diol,1TMS,isomer #2CC(=O)OC1C2OC3C=C(C)CCC3(CO[Si](C)(C)C)C(C)(C1O)C21CO12399.8Semi standard non polar33892256
3-Acetoxyscirpene-4,15-diol,2TMS,isomer #1CC(=O)OC1C2OC3C=C(C)CCC3(CO[Si](C)(C)C)C(C)(C1O[Si](C)(C)C)C21CO12406.9Semi standard non polar33892256
3-Acetoxyscirpene-4,15-diol,1TBDMS,isomer #1CC(=O)OC1C2OC3C=C(C)CCC3(CO)C(C)(C1O[Si](C)(C)C(C)(C)C)C21CO12684.1Semi standard non polar33892256
3-Acetoxyscirpene-4,15-diol,1TBDMS,isomer #2CC(=O)OC1C2OC3C=C(C)CCC3(CO[Si](C)(C)C(C)(C)C)C(C)(C1O)C21CO12641.5Semi standard non polar33892256
3-Acetoxyscirpene-4,15-diol,2TBDMS,isomer #1CC(=O)OC1C2OC3C=C(C)CCC3(CO[Si](C)(C)C(C)(C)C)C(C)(C1O[Si](C)(C)C(C)(C)C)C21CO12879.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Acetoxyscirpene-4,15-diol GC-MS (Non-derivatized) - 70eV, Positivesplash10-00du-3981000000-4b3d0372bb25dd3c66742017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Acetoxyscirpene-4,15-diol GC-MS (2 TMS) - 70eV, Positivesplash10-002g-4291200000-377d1cbcbb354bfbdd992017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Acetoxyscirpene-4,15-diol 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 - 3-Acetoxyscirpene-4,15-diol 10V, Positive-QTOFsplash10-056r-0069000000-4cb5715dfafc9651186f2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetoxyscirpene-4,15-diol 20V, Positive-QTOFsplash10-0aor-1494000000-a7912aa2bd1e4b1b706c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetoxyscirpene-4,15-diol 40V, Positive-QTOFsplash10-014i-9470000000-1bc983cfa72e54e484602016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetoxyscirpene-4,15-diol 10V, Negative-QTOFsplash10-00di-2069000000-a3625f03328c7f4a26c32016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetoxyscirpene-4,15-diol 20V, Negative-QTOFsplash10-0a4i-5393000000-af4aba9897b36e553eb92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetoxyscirpene-4,15-diol 40V, Negative-QTOFsplash10-0a4i-9700000000-052d99ea358f2383c4652016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetoxyscirpene-4,15-diol 10V, Positive-QTOFsplash10-004i-0029000000-ef8f490d2b19b4246c792021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetoxyscirpene-4,15-diol 20V, Positive-QTOFsplash10-056r-0098000000-7e9c9a2fe6b2ce0284502021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetoxyscirpene-4,15-diol 40V, Positive-QTOFsplash10-0k97-8691000000-ccae418670c4f63445f92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetoxyscirpene-4,15-diol 10V, Negative-QTOFsplash10-00di-0009000000-fdc1f5bf2fb6e471fcb92021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetoxyscirpene-4,15-diol 20V, Negative-QTOFsplash10-03k9-0095000000-0fab9f43e4548f091c8a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Acetoxyscirpene-4,15-diol 40V, Negative-QTOFsplash10-0gx0-1090000000-592db9b2f315c39b85cc2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB013094
KNApSAcK IDC00035767
Chemspider ID4509341
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5352461
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. (). 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.