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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:49:21 UTC
Update Date2023-02-21 17:21:58 UTC
HMDB IDHMDB0032355
Secondary Accession Numbers
  • HMDB32355
Metabolite Identification
Common Name(+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one
Description(+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol (+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one is a fruity, melon, and tobacco tasting compound. Based on a literature review very few articles have been published on (+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one.
Structure
Data?1677000118
Synonyms
ValueSource
(e)-5-Isopropyl-8-methylnona-6,8-dien-2-oneHMDB
(R-(e))-5-Isopropyl-8-methylnona-6,8-dien-2-oneHMDB
8-Methyl-5-(1-methylethyl)-(e)-6,8-nonadien-2-oneHMDB
8-Methyl-5-isopropyl-6,8-nonadiene-2-oneHMDB
SolanoneHMDB
Chemical FormulaC13H22O
Average Molecular Weight194.3132
Monoisotopic Molecular Weight194.167065326
IUPAC Name(6E)-8-methyl-5-(propan-2-yl)nona-6,8-dien-2-one
Traditional Name(6E)-5-isopropyl-8-methylnona-6,8-dien-2-one
CAS Registry Number2278-53-7
SMILES
CC(C)C(CCC(C)=O)\C=C\C(C)=C
InChI Identifier
InChI=1S/C13H22O/c1-10(2)6-8-13(11(3)4)9-7-12(5)14/h6,8,11,13H,1,7,9H2,2-5H3/b8-6+
InChI KeyPQDRXUSSKFWCFA-SOFGYWHQSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentKetones
Alternative Parents
Substituents
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • 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 Point238.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility11.33 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.887 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
logP4.04ALOGPS
logP3.63ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)19.64ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity62.97 m³·mol⁻¹ChemAxon
Polarizability24.36 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]+151.24731661259
DarkChem[M-H]-146.09931661259
DeepCCS[M+H]+150.8730932474
DeepCCS[M-H]-148.51230932474
DeepCCS[M-2H]-183.4630932474
DeepCCS[M+Na]+158.95430932474
AllCCS[M+H]+148.932859911
AllCCS[M+H-H2O]+145.232859911
AllCCS[M+NH4]+152.432859911
AllCCS[M+Na]+153.432859911
AllCCS[M-H]-151.032859911
AllCCS[M+Na-2H]-152.432859911
AllCCS[M+HCOO]-154.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-oneCC(C)C(CCC(C)=O)\C=C\C(C)=C1744.5Standard polar33892256
(+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-oneCC(C)C(CCC(C)=O)\C=C\C(C)=C1406.9Standard non polar33892256
(+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-oneCC(C)C(CCC(C)=O)\C=C\C(C)=C1378.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one,1TMS,isomer #1C=C(C)/C=C/C(CC=C(C)O[Si](C)(C)C)C(C)C1555.5Semi standard non polar33892256
(+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one,1TMS,isomer #1C=C(C)/C=C/C(CC=C(C)O[Si](C)(C)C)C(C)C1559.0Standard non polar33892256
(+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one,1TMS,isomer #2C=C(C)/C=C/C(CCC(=C)O[Si](C)(C)C)C(C)C1528.5Semi standard non polar33892256
(+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one,1TMS,isomer #2C=C(C)/C=C/C(CCC(=C)O[Si](C)(C)C)C(C)C1563.8Standard non polar33892256
(+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one,1TBDMS,isomer #1C=C(C)/C=C/C(CC=C(C)O[Si](C)(C)C(C)(C)C)C(C)C1799.9Semi standard non polar33892256
(+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one,1TBDMS,isomer #1C=C(C)/C=C/C(CC=C(C)O[Si](C)(C)C(C)(C)C)C(C)C1786.5Standard non polar33892256
(+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one,1TBDMS,isomer #2C=C(C)/C=C/C(CCC(=C)O[Si](C)(C)C(C)(C)C)C(C)C1783.1Semi standard non polar33892256
(+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one,1TBDMS,isomer #2C=C(C)/C=C/C(CCC(=C)O[Si](C)(C)C(C)(C)C)C(C)C1782.7Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-a1108ec371ac85a499972017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one 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 - (+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one 10V, Positive-QTOFsplash10-002b-0900000000-b921b27767a88663057b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one 20V, Positive-QTOFsplash10-000i-4900000000-0224f4b2d4320bf2622b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one 40V, Positive-QTOFsplash10-066r-9200000000-b2920045038dae0e2d452017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one 10V, Negative-QTOFsplash10-0006-0900000000-b096e71be111b97f400b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one 20V, Negative-QTOFsplash10-0006-2900000000-fa98cf80c3f6b6bc725e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one 40V, Negative-QTOFsplash10-0a4i-9400000000-e2a02e5295bf096add782017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one 10V, Negative-QTOFsplash10-0006-0900000000-f4ac9f2710ef63610b812021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one 20V, Negative-QTOFsplash10-0a4l-7900000000-6ed8f0dfee469bbf776e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one 40V, Negative-QTOFsplash10-0a4i-9200000000-d18d0d55eefa9c2d46102021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one 10V, Positive-QTOFsplash10-0apj-9600000000-1dcc26cc85fa646687392021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one 20V, Positive-QTOFsplash10-00ls-9300000000-dfa41e486d3d33760a8a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+/-)-[R-(E)]-5-Isopropyl-8-methylnona-6,8-dien-2-one 40V, Positive-QTOFsplash10-05mo-9000000000-6829a48ba5f37698b2ba2021-09-24Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-04FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-04FELIX 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 IDFDB009655
KNApSAcK IDNot Available
Chemspider ID4477935
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5319691
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1513991
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). EAFUS: Everything Added to Food in the United States.. .