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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-10-11 02:09:44 UTC
Update Date2021-09-14 15:25:44 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
Description 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

Biological location

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 Solubility0.44 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.15731661259
DarkChem[M-H]-127.6631661259
DeepCCS[M+H]+138.68630932474
DeepCCS[M-H]-136.05830932474
DeepCCS[M-2H]-172.43530932474
DeepCCS[M+Na]+147.73330932474
AllCCS[M+H]+126.732859911
AllCCS[M+H-H2O]+122.032859911
AllCCS[M+NH4]+131.032859911
AllCCS[M+Na]+132.332859911
AllCCS[M-H]-132.832859911
AllCCS[M+Na-2H]-134.632859911
AllCCS[M+HCOO]-136.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsoterpinoleneCC1CCC(C=C1)=C(C)C1314.0Standard polar33892256
IsoterpinoleneCC1CCC(C=C1)=C(C)C1043.3Standard non polar33892256
IsoterpinoleneCC1CCC(C=C1)=C(C)C1071.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isoterpinolene GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9600000000-bbea39718e4d1c7e52872017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isoterpinolene 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 - Isoterpinolene 10V, Negative-QTOFsplash10-000i-0900000000-739cc8a840f940822f5f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoterpinolene 20V, Negative-QTOFsplash10-000i-1900000000-d663a15e977b1ac38ac42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoterpinolene 40V, Negative-QTOFsplash10-014u-7900000000-183027babbe8ad0fa6c12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoterpinolene 10V, Negative-QTOFsplash10-000i-0900000000-a013b4ae27f975ab56212021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoterpinolene 20V, Negative-QTOFsplash10-000i-0900000000-a013b4ae27f975ab56212021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoterpinolene 40V, Negative-QTOFsplash10-0159-0900000000-6ed57a7d72fafdd314a12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoterpinolene 10V, Positive-QTOFsplash10-000i-3900000000-666f5e554b0b76460f732016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoterpinolene 20V, Positive-QTOFsplash10-000j-9500000000-0c79851f3f2827859c812016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoterpinolene 40V, Positive-QTOFsplash10-1000-9100000000-370b98761179b23bf89c2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoterpinolene 10V, Positive-QTOFsplash10-000b-9200000000-0ce4e0450a3e41738eee2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoterpinolene 20V, Positive-QTOFsplash10-005d-9000000000-e801d0663f62929036942021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isoterpinolene 40V, Positive-QTOFsplash10-002f-9000000000-87ff1d976d9a0e7ff8af2021-09-23Wishart 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 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 ID88840
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. 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 ]
  2. 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 ]
  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]