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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:55:54 UTC
Update Date2022-03-07 03:17:48 UTC
HMDB IDHMDB0061852
Secondary Accession Numbers
  • HMDB61852
Metabolite Identification
Common NameYlangene
DescriptionYlangene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Ylangene is possibly neutral.
Structure
Data?1563866238
SynonymsNot Available
Chemical FormulaC15H24
Average Molecular Weight204.3511
Monoisotopic Molecular Weight204.187800768
IUPAC Name(1R,8R)-1,3-dimethyl-8-(propan-2-yl)tricyclo[4.4.0.0²,⁷]dec-3-ene
Traditional Name(1R,8R)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0²,⁷]dec-3-ene
CAS Registry NumberNot Available
SMILES
[H]C12CC=C(C)C3([H])C1([H])[C@]([H])(CC[C@]23C)C(C)C
InChI Identifier
InChI=1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)14(15)13(11)12/h5,9,11-14H,6-8H2,1-4H3/t11-,12?,13?,14?,15-/m1/s1
InChI KeyVLXDPFLIRFYIME-XTLGRWLVSA-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
  • Copaane sesquiterpenoid
  • Sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
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 Solubility0.0018 g/LALOGPS
logP3.75ALOGPS
logP4.09ChemAxon
logS-5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity65.77 m³·mol⁻¹ChemAxon
Polarizability26.07 ųChemAxon
Number of Rings3ChemAxon
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]+150.09731661259
DarkChem[M-H]-149.61931661259
DeepCCS[M-2H]-188.46230932474
DeepCCS[M+Na]+163.35630932474
AllCCS[M+H]+147.332859911
AllCCS[M+H-H2O]+143.532859911
AllCCS[M+NH4]+150.832859911
AllCCS[M+Na]+151.832859911
AllCCS[M-H]-158.332859911
AllCCS[M+Na-2H]-158.732859911
AllCCS[M+HCOO]-159.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Ylangene[H]C12CC=C(C)C3([H])C1([H])[C@]([H])(CC[C@]23C)C(C)C1654.8Standard polar33892256
Ylangene[H]C12CC=C(C)C3([H])C1([H])[C@]([H])(CC[C@]23C)C(C)C1432.6Standard non polar33892256
Ylangene[H]C12CC=C(C)C3([H])C1([H])[C@]([H])(CC[C@]23C)C(C)C1433.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Ylangene GC-MS (Non-derivatized) - 70eV, Positivesplash10-000l-4900000000-a3529081bb30d315558d2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Ylangene 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 - Ylangene 10V, Negative-QTOFsplash10-0udi-0090000000-63104082a983374bf1f22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ylangene 20V, Negative-QTOFsplash10-0udi-0090000000-ab31c116f1847bfe7d342017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ylangene 40V, Negative-QTOFsplash10-0f79-1920000000-468aa00ce89c65f1429e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ylangene 10V, Negative-QTOFsplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ylangene 20V, Negative-QTOFsplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ylangene 40V, Negative-QTOFsplash10-0udi-0090000000-38c7ce47d88d85e5b4872021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ylangene 10V, Positive-QTOFsplash10-0a4i-0190000000-650f0fbf2d445278e2de2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ylangene 20V, Positive-QTOFsplash10-0a4i-5960000000-bad60089bbc389ec0c9c2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ylangene 40V, Positive-QTOFsplash10-0ap0-9200000000-3e2f7730530d7b1bce882017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ylangene 10V, Positive-QTOFsplash10-0a4i-0290000000-7d254498a5da64fcddbd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ylangene 20V, Positive-QTOFsplash10-00di-5920000000-100ae5805ad5aa0f96612021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Ylangene 40V, Positive-QTOFsplash10-00o3-9100000000-26f71b73fc69959ecca22021-09-23Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound124202084
PDB IDNot Available
ChEBI ID88648
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. Schreier P, Drawert F, Junker A: [Sesquiterpene hydrocarbons from grapes (author's transl)]. Z Lebensm Unters Forsch. 1976;160(3):271-4. [PubMed:983335 ]
  2. Duh CY, El-Gamal AA, Song PY, Wang SK, Dai CF: Steroids and sesquiterpenoids from the soft corals Dendronephthya gigantea and Lemnalia cervicorni. J Nat Prod. 2004 Oct;67(10):1650-3. [PubMed:15497934 ]
  3. Parker M, Pollnitz AP, Cozzolino D, Francis IL, Herderich MJ: Identification and quantification of a marker compound for 'pepper' aroma and flavor in shiraz grape berries by combination of chemometrics and gas chromatography-mass spectrometry. J Agric Food Chem. 2007 Jul 25;55(15):5948-55. Epub 2007 Jun 20. [PubMed:17580875 ]
  4. Lodewyk MW, Gutta P, Tantillo DJ: Computational studies on biosynthetic carbocation rearrangements leading to sativene, cyclosativene, alpha-ylangene, and beta-ylangene. J Org Chem. 2008 Sep 5;73(17):6570-9. doi: 10.1021/jo800868r. Epub 2008 Aug 6. [PubMed:18681400 ]
  5. Cheng SY, Lin EH, Huang JS, Wen ZH, Duh CY: Ylangene-type and nardosinane-type sesquiterpenoids from the soft corals Lemnalia flava and Paralemnalia thyrsoides. Chem Pharm Bull (Tokyo). 2010 Mar;58(3):381-5. [PubMed:20190445 ]
  6. Hong YJ, Tantillo DJ: Theoretical calculations on carbocations involved in the biosynthesis of bergamotenes and related terpenes--the same and not the same. Chem Commun (Camb). 2012 Feb 1;48(10):1571-3. doi: 10.1039/c1cc14414f. Epub 2011 Oct 7. [PubMed:21983931 ]
  7. Xio YJ, Su JH, Chen BW, Tseng YJ, Wu YC, Sheu JH: Oxygenated ylangene-derived sesquiterpenoids from the soft coral Lemnalia philippinensis. Mar Drugs. 2013 Sep 30;11(10):3735-41. doi: 10.3390/md11103735. [PubMed:24084789 ]
  8. Flath RA, Cunningham RT, Mon TR, John JO: Male lures for mediterranean fruitfly (Ceratitis capitata wied.): Structural analogs of alpha-copaene. J Chem Ecol. 1994 Oct;20(10):2595-609. doi: 10.1007/BF02036194. [PubMed:24241834 ]
  9. Flath RA, Cunningham RT, Mon TR, John JO: Additional male mediterranean fruitfly (Ceratitis capitata wied.) Attractants from Angelica seed oil (Angelica archangelica L.). J Chem Ecol. 1994 Aug;20(8):1969-84. doi: 10.1007/BF02066237. [PubMed:24242723 ]
  10. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.