Showing Compound Card for (1R)-(+)-trans-isolimonene (CDB000485)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesXML
Record Information
Version1.0
Created at2020-03-19 00:39:33 UTC
Updated at2020-12-07 19:07:27 UTC
CannabisDB IDCDB000485
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(1R)-(+)-trans-isolimonene
Description(1R)-(+)-Trans-Isolimonene 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. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-eritritol-phosphate (MEP) pathway in plant cell plastids. Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. (1R) -(+)-trans-isolimonene is possibly neutral and it is one of the terpenes that are known in cannabis plant (PMID: 25454145 ). It was also identified in the essential oil from Salvia sharifii (7.0% relative to total oil constituents) (DOI: 10.1080/0972060X.2014.895684) and Thuja orientalis (1716.31 mg/L from wild leaves, 753.10 mg/L from planted leaves) (DOI: 10.1080/0972060X.2019.1689177). A study has shown that (1R) -(+)-trans-isolimonene has no antibacterial and antifungal effects (PMID: 8693045 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC10H16
Average Molecular Weight136.23
Monoisotopic Molecular Weight136.1252
IUPAC Name(3R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-1-ene
Traditional Name(3R,6R)-3-methyl-6-(prop-1-en-2-yl)cyclohex-1-ene
CAS Registry NumberNot Available
SMILES
C[C@@H]1CC[C@H](C=C1)C(C)=C
InChI Identifier
InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,9-10H,1,5,7H2,2-3H3/t9-,10-/m0/s1
InChI KeyTWCNAXRPQBLSNO-UWVGGRQHSA-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

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.23ALOGPS
logP3.26ChemAxon
logS-3.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity46.75 m³·mol⁻¹ChemAxon
Polarizability17.21 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(1R)-(+)-trans-isolimonene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-006x-9200000000-c60a535fd9fd31f8b94fSpectrum
Predicted GC-MS(1R)-(+)-trans-isolimonene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1900000000-f24bb5ad7cf8034160c62017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9500000000-6ed3371f457ae333b3072017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pvi-9000000000-7ec656f36492872b10392017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-0572dada5d40eb9ff7912017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-bb631cf743c407b4ac0c2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00ku-4900000000-c3f14c70f20bb1a579442017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a013b4ae27f975ab56212021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-db25612f5bfd224c18c62021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-1900000000-c05c7501280e6819847a2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001s-9300000000-bb57834010cb181366822021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-005d-9000000000-6f02b8e50b22243276a12021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9000000000-66318504608d9be5cee92021-09-25View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0061793
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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 Compound78790
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Marchini M, Charvoz C, Dujourdy L, Baldovini N, Filippi JJ: Multidimensional analysis of cannabis volatile constituents: identification of 5,5-dimethyl-1-vinylbicyclo[2.1.1]hexane as a volatile marker of hashish, the resin of Cannabis sativa L. J Chromatogr A. 2014 Nov 28;1370:200-15. doi: 10.1016/j.chroma.2014.10.045. Epub 2014 Oct 23. [PubMed:25454145 ]
  2. Naigre R, Kalck P, Roques C, Roux I, Michel G: Comparison of antimicrobial properties of monoterpenes and their carbonylated products. Planta Med. 1996 Jun;62(3):275-7. doi: 10.1055/s-2006-957877. [PubMed:8693045 ]