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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2014-10-11 02:09:44 UTC
Update Date2019-07-23 07:17:29 UTC
HMDB IDHMDB0061938
Secondary Accession Numbers
  • HMDB61938
Metabolite Identification
Common NameIsoterpinolene
DescriptionIsoterpinolene belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
Structure
Data?1563866248
SynonymsNot Available
Chemical FormulaC10H16
Average Molecular Weight136.234
Monoisotopic Molecular Weight136.125200512
IUPAC Name3-methyl-6-(propan-2-ylidene)cyclohex-1-ene
Traditional Name3-methyl-6-(propan-2-ylidene)cyclohex-1-ene
CAS Registry NumberNot Available
SMILES
CC1CCC(C=C1)=C(C)C
InChI Identifier
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,9H,5,7H2,1-3H3
InChI KeyCIPXOBMYVWRNLL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentMenthane monoterpenoids
Alternative Parents
Substituents
  • P-menthane monoterpenoid
  • Monocyclic monoterpenoid
  • Branched unsaturated hydrocarbon
  • Cycloalkene
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring 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 Solubility0.44 g/LALOGPS
logP4.29ALOGPS
logP3.16ChemAxon
logS-2.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.55 m³·mol⁻¹ChemAxon
Polarizability17.58 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9600000000-bbea39718e4d1c7e5287JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-3900000000-666f5e554b0b76460f73JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000j-9500000000-0c79851f3f2827859c81JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-1000-9100000000-370b98761179b23bf89cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-739cc8a840f940822f5fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-1900000000-d663a15e977b1ac38ac4JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014u-7900000000-183027babbe8ad0fa6c1JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003863
KNApSAcK IDNot Available
Chemspider ID92519
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound102443
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Tsoukatou M, Tsitsimpikou C, Vagias C, Roussis V: Chemical intra-Mediterranean variation and insecticidal activity of Crithmum maritimum. Z Naturforsch C. 2001 Mar-Apr;56(3-4):211-5. [PubMed:11371010 ]
  2. Alali F, Al-Lafi T: GC-MS analysis and bioactivity testing of the volatile oil from the leaves of the toothbrush tree Salvadora persica L. Nat Prod Res. 2003 Jun;17(3):189-94. [PubMed:12737403 ]
  3. Li Z, Liu S: [Study on chemical constituents of essential oil of Vitexd rotundifolia L. by gas chromatography/mass spectrometry]. Se Pu. 1997 Jul;15(4):344-6. [PubMed:15739473 ]
  4. Taherpour AA, Maroofi H, Bajelani O, Larijani K: Chemical composition of the essential oil of Valeriana alliariifolia Adams of Iran. Nat Prod Res. 2010 Jun;24(10):973-8. doi: 10.1080/14786410902900010. [PubMed:20496237 ]
  5. Silva AG, Almeida DL, Ronchi SN, Bento AC, Scherer R, Ramos AC, Cruz ZM: The essential oil of Brazilian pepper, Schinus terebinthifolia Raddi in larval control of Stegomyia aegypti (Linnaeus, 1762). Parasit Vectors. 2010 Aug 27;3:79. doi: 10.1186/1756-3305-3-79. [PubMed:20799936 ]
  6. Akhtar J, Siddique KM, Bi S, Mujeeb M: A review on phytochemical and pharmacological investigations of miswak (Salvadora persica Linn). J Pharm Bioallied Sci. 2011 Jan;3(1):113-7. doi: 10.4103/0975-7406.76488. [PubMed:21430961 ]
  7. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  12. David W. Parker, 'Isoterpinolene-maleic anhydride copolymers.' U.S. Patent US4975504, issued January, 1944. [Link]