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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2014-10-08 15:54:21 UTC
Update Date2017-10-23 19:16:00 UTC
HMDB IDHMDB0061779
Secondary Accession Numbers
  • HMDB61779
Metabolite Identification
Common NameIsocaryophyllene
DescriptionIsocaryophyllene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
Structure
Thumb
Synonyms
ValueSource
Gamma-CaryophylleneChEMBL
g-CaryophylleneGenerator
γ-caryophylleneGenerator
trans-CaryophylleneMeSH
(e)-beta-CaryophylleneMeSH
Caryophyllene, (r*,4Z,9S*)-(+-)-isomerMeSH
beta-CaryophylleneMeSH
CaryophylleneMeSH
Caryophyllene, (R-(r*,4E,9S))-isomerMeSH
Caryophyllene, (R-(r*,4Z,9S*))-isomerMeSH
Caryophyllene, (S-(r*,4E,9S*))-isomerMeSH
Caryophyllene, (S-(r*,4Z,9S*))-isomerMeSH
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
C\C1=C\CCC(=C)[C@H]2CC(C)(C)[C@@H]2CC1
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
DescriptionThis compound belongs to the class of chemical entities known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassPrenol lipids
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:

  Biofluid and excreta:

  Subcellular:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

    Chemical reaction:

    Biochemical process:

    Cellular process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-2900000000-666e65f6b538d4a0eeeaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-de2a6b536bb38d3c2951View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-3950000000-6dc317c917393691dfefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f7a-6900000000-5f5ee8e9f24e0511e186View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-d6c31402204fa765cbc0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0290000000-48307d26c19d0c84ce74View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002r-2900000000-741197d2390e8d4bc104View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Saliva
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC09691
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5281522
PDB IDNot Available
ChEBI 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]