Showing Compound Card for trans-Sabinene hydrate (CDB000302)

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Record Information
Version1.0
Created at2020-03-19 00:29:49 UTC
Updated at2020-11-18 16:35:03 UTC
CannabisDB IDCDB000302
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Nametrans-Sabinene hydrate
DescriptionTrans-Sabinene hydrate, also known as trans-4-thujanol, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. 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-erythritol-phosphate (MEP) pathway in plant cell plastids (PMID: 7640522 ). 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. Trans-Sabinene hydrate is a neutral, hydrophobic molecule that is practically insoluble in water. It has a woody, balsamic odor. It occurs naturally in a wide number of plants and plant oils including lemon, lime, grapefruit, blood orange, mandarin orange, orange peel, rosemary, nutmeg, pot marjoram, common oregano, and mentha (mint), which makes (+)-trans-sabinene hydrate a potential biomarker for the consumption of these food products. Trans-Sabinene hydrate is one of the terpenoids that has been identified in cannabis plants only in trace amounts (PMID: 6991645 ). It is one of more than 140 terpenoids found in cannabis and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(+)-trans-Sabinene hydric acidGenerator
Chemical FormulaC10H18O
Average Molecular Weight154.25
Monoisotopic Molecular Weight154.1358
IUPAC Name(1S,2S,5R)-2-methyl-5-(propan-2-yl)bicyclo[3.1.0]hexan-2-ol
Traditional Name(1S,2S,5R)-5-isopropyl-2-methylbicyclo[3.1.0]hexan-2-ol
CAS Registry NumberNot Available
SMILES
CC(C)[C@@]12C[C@@H]1[C@@](C)(O)CC2
InChI Identifier
InChI=1S/C10H18O/c1-7(2)10-5-4-9(3,11)8(10)6-10/h7-8,11H,4-6H2,1-3H3/t8-,9+,10-/m1/s1
InChI KeyKXSDPILWMGFJMM-KXUCPTDWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
  • Thujane monoterpenoid
  • Tertiary alcohol
  • Cyclic alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.12ALOGPS
logP1.89ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)19.13ChemAxon
pKa (Strongest Basic)-0.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.55 m³·mol⁻¹ChemAxon
Polarizability18.66 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MStrans-Sabinene hydrate, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0900000000-bb4d810a903b491686452016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-3900000000-86e0dbc0c378d01fe9ab2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05gr-9600000000-5d9c2e6a3159571473922016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-e9344613e0d30c201ac72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-f35baa9b2bece161cc902016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0k9i-4900000000-18c55cbbe6856fe136522016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052e-8900000000-0f282cd4bfdb147f67512021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9300000000-35cb41d240c8e510afd72021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-85ade551b4aacc4fd8e02021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-d2363ae8d4dbdcccda802021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-d2363ae8d4dbdcccda802021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0900000000-f0b940d91fca8f32df512021-10-21View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Sensi Star (Pure Indica)Detected and Quantified0.07 +/- 0.00 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0301816
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB001454
KNApSAcK IDNot Available
Chemspider ID9403968
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11228920
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]