Showing Compound Card for (+)-cis-Sabinol (CDB000205)

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Record Information
Version1.0
Created at2020-03-18 23:28:40 UTC
Updated at2020-11-18 16:34:55 UTC
CannabisDB IDCDB000205
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(+)-cis-Sabinol
Description(+)-cis-Sabinol belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Thus, (+)-cis-sabinol is an isoprenoid lipid molecule. 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 the plastids (PMID: 23746261 ). 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. (+)-cis-Sabinol is very hydrophobic, practically insoluble in water, and relatively neutral. (+)-cis-Sabinol is found in cannabis plants (PMID:6991645 ) Artemisia annuaand ( Ref:DOI ) and in herbal plant Dendranthema indicum (PMID: 29510531 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1S,3R,5S)-SabinolChEBI
SabinolChEBI
Sabinol, (1alpha,3alpha,5alpha)-isomerMeSH
Sabinol, (1alpha,3beta,5alpha)-isomerMeSH
Chemical FormulaC10H16O
Average Molecular Weight152.23
Monoisotopic Molecular Weight152.1201
IUPAC Name(1S,3R,5S)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-ol
Traditional Name(+)-sabinol
CAS Registry Number471-16-9
SMILES
CC(C)[C@@]12C[C@@H]1C(=C)[C@H](O)C2
InChI Identifier
InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6,8-9,11H,3-5H2,1-2H3/t8-,9-,10+/m1/s1
InChI KeyMDFQXBNVOAKNAY-BBBLOLIVSA-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
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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
logP1.9ALOGPS
logP1.63ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)17.87ChemAxon
pKa (Strongest Basic)-1.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area20.23 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.17 m³·mol⁻¹ChemAxon
Polarizability18.1 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9200000000-165238e163a314643e1a2015-03-01View Spectrum
Predicted GC-MS(+)-cis-Sabinol, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f79-0900000000-5e0db9e024b9dbfce4552016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-4900000000-e2dade9685014855f8682016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fai-9200000000-0c718ce623c15256b5162016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-9997279a315e37102de12016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-9a0e5dc00a295fd21fb82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f7c-5900000000-e6189ad3fa3c8e0765ed2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0900000000-c373c9eea3cebf186f532021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0900000000-a072b2fda1e9be2203c52021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0py0-5900000000-4bb331a77f6e6821a1182021-10-11View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9400000000-6ac8a4cc1288673bfbfa2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9100000000-270be2a704703cba55cf2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f6x-9400000000-f19b84e9eefe1ffbc0002021-10-21View Spectrum
NMR
TypeDescriptionView
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0302768
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB006162
KNApSAcK IDC00000831
Chemspider ID84964
KEGG Compound IDC02213
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID15387
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. Fan S, Chang J, Zong Y, Hu G, Jia J: GC-MS Analysis of the Composition of the Essential Oil from Dendranthema indicum Var. Aromaticum Using Three Extraction Methods and Two Columns. Molecules. 2018 Mar 4;23(3). pii: molecules23030576. doi: 10.3390/molecules23030576. [PubMed:29510531 ]
  3. Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. [PubMed:23746261 ]