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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 21:13:35 UTC
Update Date2022-03-07 02:54:48 UTC
HMDB IDHMDB0036163
Secondary Accession Numbers
  • HMDB36163
Metabolite Identification
Common Namebeta-Sesquiphellandrene
Descriptionbeta-Sesquiphellandrene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on beta-Sesquiphellandrene.
Structure
Data?1563862831
Synonyms
ValueSource
b-SesquiphellandreneGenerator
Β-sesquiphellandreneGenerator
3-(1,5-Dimethyl-4-hexenyl)-6-methylene-1-cyclohexeneMetaCyc, HMDB
(-)-beta-SesquiphellandreneHMDB
3-(1,5-Dimethyl-4-hexenyl)-6-methylenecyclohexene, 9ciHMDB
beta-SesquiphellandereneHMDB
SesquiphellandreneHMDB
Chemical FormulaC15H24
Average Molecular Weight204.357
Monoisotopic Molecular Weight204.187800773
IUPAC Name3-(6-methylhept-5-en-2-yl)-6-methylidenecyclohex-1-ene
Traditional Name3-(6-methylhept-5-en-2-yl)-6-methylidenecyclohex-1-ene
CAS Registry Number20307-83-9
SMILES
CC(CCC=C(C)C)C1CCC(=C)C=C1
InChI Identifier
InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,10,14-15H,3,5,7,9,11H2,1-2,4H3
InChI KeyPHWISBHSBNDZDX-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Bisabolane sesquiterpenoid
  • Sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Cycloalkene
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point270.00 to 272.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility0.013 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.522 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.002 g/LALOGPS
logP5.71ALOGPS
logP4.92ChemAxon
logS-5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity70.55 m³·mol⁻¹ChemAxon
Polarizability26.18 ųChemAxon
Number of Rings1ChemAxon
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]+150.51831661259
DarkChem[M-H]-148.56431661259
DeepCCS[M+H]+152.17230932474
DeepCCS[M-H]-149.81430932474
DeepCCS[M-2H]-185.00330932474
DeepCCS[M+Na]+160.37330932474
AllCCS[M+H]+150.132859911
AllCCS[M+H-H2O]+146.132859911
AllCCS[M+NH4]+153.832859911
AllCCS[M+Na]+154.932859911
AllCCS[M-H]-156.532859911
AllCCS[M+Na-2H]-157.332859911
AllCCS[M+HCOO]-158.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
beta-SesquiphellandreneCC(CCC=C(C)C)C1CCC(=C)C=C11716.3Standard polar33892256
beta-SesquiphellandreneCC(CCC=C(C)C)C1CCC(=C)C=C11487.7Standard non polar33892256
beta-SesquiphellandreneCC(CCC=C(C)C)C1CCC(=C)C=C11496.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - beta-Sesquiphellandrene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9400000000-da410262a5aa40a5141e2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Sesquiphellandrene 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 - beta-Sesquiphellandrene 10V, Positive-QTOFsplash10-0a4i-1590000000-ee4910c0211e359eb6d62015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 20V, Positive-QTOFsplash10-0ce9-5920000000-3de3009aefc4652d9bc32015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 40V, Positive-QTOFsplash10-0gb9-9400000000-eb663137c6ef2baa559f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 10V, Negative-QTOFsplash10-0udi-0090000000-62a38848141bb5a59eb52015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 20V, Negative-QTOFsplash10-0udi-0190000000-ff4a8c08da39e9922cfb2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 40V, Negative-QTOFsplash10-000i-4900000000-1842c3f2bfe51c2cf8502015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 10V, Positive-QTOFsplash10-05gi-9600000000-56e4e42e5eedecf82f442021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 20V, Positive-QTOFsplash10-00kf-9200000000-9e8b6a8db07464f4f7242021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 40V, Positive-QTOFsplash10-0006-9100000000-3d87fa454ae9477f27fa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 10V, Negative-QTOFsplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 20V, Negative-QTOFsplash10-0udi-0290000000-2cb14f58730ed114d3052021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Sesquiphellandrene 40V, Negative-QTOFsplash10-0udi-4490000000-6bc908356192dde2f9722021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Female
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB015016
KNApSAcK IDC00056123
Chemspider ID453379
KEGG Compound IDC16776
BioCyc IDCPD-8247
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound519764
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1103651
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nazaruk J, Kalemba D: Chemical composition of the essential oils from the roots of Erigeron acris L. and Erigeron annuus (L.) Pers. Molecules. 2009 Jul 9;14(7):2458-65. doi: 10.3390/molecules14072458. [PubMed:19633616 ]
  2. Zhan K, Wang C, Xu K, Yin H: [Analysis of volatile and non-volatile compositions in ginger oleoresin by gas chromatography-mass spectrometry]. Se Pu. 2008 Nov;26(6):692-6. [PubMed:19253546 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.