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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:54:21 UTC
Update Date2022-03-07 03:17:46 UTC
HMDB IDHMDB0061779
Secondary Accession Numbers
  • HMDB61779
Metabolite Identification
Common NameIsocaryophyllene
DescriptionIsocaryophyllene, also known as Gamma-caryophyllene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, isocaryophyllene is considered to be an isoprenoid lipid molecule. Isocaryophyllene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866230
Synonyms
ValueSource
Gamma-CaryophylleneHMDB
g-CaryophylleneHMDB
Γ-caryophylleneHMDB
Caryophyllene, (r*,4Z,9S*)-(+-)-isomerHMDB
CaryophylleneHMDB
Caryophyllene, (R-(r*,4E,9S))-isomerHMDB
Caryophyllene, (R-(r*,4Z,9S*))-isomerHMDB
Caryophyllene, (S-(r*,4E,9S*))-isomerHMDB
Caryophyllene, (S-(r*,4Z,9S*))-isomerHMDB
Chemical FormulaC15H24
Average Molecular Weight204.357
Monoisotopic Molecular Weight204.187800773
IUPAC Name(1R,4Z,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
Traditional Nameisocaryophyllene
CAS Registry Number118-65-0
SMILES
[H][C@]12CC(C)(C)[C@]1([H])CC\C(C)=C/CCC2=C
InChI Identifier
InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6-/t13-,14-/m1/s1
InChI KeyNPNUFJAVOOONJE-FLFDDASRSA-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
  • Caryophyllane sesquiterpenoid
  • Sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

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 Solubility0.003 g/LALOGPS
logP5.35ALOGPS
logP4.52ChemAxon
logS-4.8ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity67.45 m³·mol⁻¹ChemAxon
Polarizability26 ųChemAxon
Number of Rings2ChemAxon
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]+148.06231661259
DarkChem[M-H]-147.79931661259
DeepCCS[M-2H]-187.39630932474
DeepCCS[M+Na]+162.46730932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isocaryophyllene[H][C@]12CC(C)(C)[C@]1([H])CC\C(C)=C/CCC2=C1644.0Standard polar33892256
Isocaryophyllene[H][C@]12CC(C)(C)[C@]1([H])CC\C(C)=C/CCC2=C1447.0Standard non polar33892256
Isocaryophyllene[H][C@]12CC(C)(C)[C@]1([H])CC\C(C)=C/CCC2=C1442.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isocaryophyllene GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-2900000000-666e65f6b538d4a0eeea2017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isocaryophyllene 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 - Isocaryophyllene 10V, Positive-QTOFsplash10-0a4i-0290000000-de2a6b536bb38d3c29512017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocaryophyllene 20V, Positive-QTOFsplash10-0a4i-3950000000-6dc317c917393691dfef2017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocaryophyllene 40V, Positive-QTOFsplash10-0f7a-6900000000-5f5ee8e9f24e0511e1862017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocaryophyllene 10V, Negative-QTOFsplash10-0udi-0090000000-d6c31402204fa765cbc02017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocaryophyllene 20V, Negative-QTOFsplash10-0udi-0290000000-48307d26c19d0c84ce742017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocaryophyllene 40V, Negative-QTOFsplash10-002r-2900000000-741197d2390e8d4bc1042017-06-28Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocaryophyllene 10V, Positive-QTOFsplash10-0a4i-0190000000-18da8cef0774773a46642021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocaryophyllene 20V, Positive-QTOFsplash10-0a4j-7930000000-0de14671750170215e532021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocaryophyllene 40V, Positive-QTOFsplash10-0a4m-9400000000-c0fc2f9446fefc8829182021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocaryophyllene 10V, Negative-QTOFsplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocaryophyllene 20V, Negative-QTOFsplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isocaryophyllene 40V, Negative-QTOFsplash10-0udi-0980000000-9f708eefb54c5860f0032021-09-23Wishart 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 IDC00012474
Chemspider IDNot Available
KEGG Compound IDC09691
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281522
PDB IDNot Available
ChEBI ID5993
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. Jelen HH, Mirocha CJ, Wasowicz E, Kaminski E: Production of volatile sesquiterpenes by Fusarium sambucinum strains with different abilities to synthesize trichothecenes. Appl Environ Microbiol. 1995 Nov;61(11):3815-20. [PubMed:8526491 ]
  2. Demirci B, Baser KH, Ozek T, Demirci F: Betulenols from Betula species. Planta Med. 2000 Jun;66(5):490-3. [PubMed:10909279 ]
  3. Hernandez T, Canales M, Avila JG, Garcia AM, Martinez A, Caballero J, de Vivar AR, Lira R: Composition and antibacterial activity of essential oil of Lantana achyranthifolia Desf. (Verbenaceae). J Ethnopharmacol. 2005 Jan 15;96(3):551-4. [PubMed:15619577 ]
  4. Ricci D, Fraternale D, Giamperi L, Bucchini A, Epifano F, Burini G, Curini M: Chemical composition, antimicrobial and antioxidant activity of the essential oil of Teucrium marum (Lamiaceae). J Ethnopharmacol. 2005 Apr 8;98(1-2):195-200. [PubMed:15763383 ]
  5. Sabulal B, Dan M, J AJ, Kurup R, Pradeep NS, Valsamma RK, George V: Caryophyllene-rich rhizome oil of Zingiber nimmonii from South India: Chemical characterization and antimicrobial activity. Phytochemistry. 2006 Nov;67(22):2469-73. Epub 2006 Sep 14. [PubMed:16973189 ]
  6. Legault J, Pichette A: Potentiating effect of beta-caryophyllene on anticancer activity of alpha-humulene, isocaryophyllene and paclitaxel. J Pharm Pharmacol. 2007 Dec;59(12):1643-7. [PubMed:18053325 ]
  7. Ashitani T, Borg-Karlson AK, Fujita K, Nagahama S: Reaction mechanism of direct episulfidation of caryophyllene and humulene. Nat Prod Res. 2008 Apr 15;22(6):495-8. doi: 10.1080/14786410701591903. [PubMed:18415856 ]
  8. Sousa EO, Silva NF, Rodrigues FF, Campos AR, Lima SG, Costa JG: Chemical composition and resistance-modifying effect of the essential oil of Lantana camara Linn. Pharmacogn Mag. 2010 Apr;6(22):79-82. doi: 10.4103/0973-1296.62890. Epub 2010 May 5. [PubMed:20668570 ]
  9. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  14. Qinghe Zhang, Armenek Margaryan, Rodney G. Schneidmiller, 'METHODS FOR REPELLING INSECTS USING SESQUITERPENE HYDROCARBONS AND THEIR DERIVATIVES.' U.S. Patent US20100166896, issued July 01, 2010. [Link]
  15. Qinghe Zhang, Armenek Margaryan, Rodney G. Schneidmiller, 'Methods for repelling insects using sesquiterpene hydrocarbons and their derivatives.' U.S. Patent US08057829, issued November 15, 2011. [Link]