Showing Compound Card for Sabinene (CDB000087)

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Record Information
Version1.0
Created at2020-03-18 23:24:17 UTC
Updated at2020-12-07 19:07:05 UTC
CannabisDB IDCDB000087
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameSabinene
DescriptionSabinene or 4(10)-thujene, belongs to the class of organic compounds known as bicyclic monoterpenoids which contain 2 rings fused to each other. Thus, sabinene is an isoprenoid lipid molecule. It is very hydrophobic, practically insoluble in water and relatively neutral. 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 (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. Sabinene has a citrus, pepper, and pine taste and is responsible for the spiciness of pepper. Sabinene is found in the essential oils of a variety of plants/trees including the holm oak, Norway spruce, bay laurel (Laurus nobilis). common sage, and true nutmeg (Myristica fragrans tree; PMID: 5615546 ). Sabinene is also found in trace amounts in cannabis plants (PMID: 6991645 ). Sabinene is found in highest concentrations in nutmegs, tarragons, and sweet bay and in lower concentrations in common sages, caraway, and star anises. Sabinene has also been detected in saffrons, sunflowers, yellow bell peppers, summer savories, and pepper (C. annuum). Sabinene can be used as flavorings, perfume additives, fine chemicals, and advanced biofuels. The microbial biosynthesis of sabinene has been well studied to facilitate the industrial production of this important compound (PMID: 29264773 ). Sabinene has some medicinal properties as it induced recovery of myotube shrinkage in fasting rats, suggesting that it may reverse muscle atrophy (PMID: 31597276 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(1R,5R)-1-Isopropyl-4-methylenebicyclo[3.1.0]hexaneChEBI
(1R,5R)-SabineneChEBI
(1R,5R)-(+)-4(10)-ThujeneHMDB
(1R,5R)-(+)-SabineneHMDB
(1R,5R)-4-Methylene-1-(1-methylethyl)bicyclo[3.1.0]hexaneHMDB
1-Isopropyl-4-methylenebicyclo[3.1.0]hexaneHMDB
4(10)-ThujeneHMDB
4-Methylene-1-(1-methylethyl)bicyclo[3.1.0]hexaneHMDB
SabeneneHMDB
SabinenHMDB
SabineneHMDB
(+)-4(10)-ThujeneHMDB
(+)-SabineneHMDB
d-4(10)-ThujenePhytoBank
d-SabinenePhytoBank
Chemical FormulaC10H16
Average Molecular Weight136.24
Monoisotopic Molecular Weight136.1252
IUPAC Name(1R,5R)-4-methylidene-1-(propan-2-yl)bicyclo[3.1.0]hexane
Traditional Name(+)-sabinene
CAS Registry Number2009-00-9
SMILES
CC(C)[C@@]12C[C@@H]1C(=C)CC2
InChI Identifier
InChI=1S/C10H16/c1-7(2)10-5-4-8(3)9(10)6-10/h7,9H,3-6H2,1-2H3/t9-,10-/m1/s1
InChI KeyNDVASEGYNIMXJL-NXEZZACHSA-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
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling Point163 - 164 °CWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.04ALOGPS
logP2.86ChemAxon
logS-3.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.65 m³·mol⁻¹ChemAxon
Polarizability17.24 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-MSSabinene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9200000000-6dcba8d83baca68ed92bSpectrum
Predicted GC-MSSabinene, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-1900000000-3136e5a49973e2d4b9b92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-5900000000-ae57d4f53c8a796d61832016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a7i-9100000000-638e2949ce61df63a67f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-360eebc69f988d8437b92016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-f19e62bab67672d011722016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014r-5900000000-3caad63de3717d5084eb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0007-9200000000-9b768262d1cb11f6f1e42021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0016-9300000000-1b1afd2ab94c87902ffa2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-c6988a878e76669ec23d2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0900000000-a013b4ae27f975ab56212021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0900000000-a013b4ae27f975ab56212021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-8900000000-e2c494c1ae77db4c3c522021-09-23View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Sensi StarDetected and Quantified0.05 mg/g dry wt
    • David S. Wishart,...
 details
Sensi Star (Pure Indica)Detected and Quantified0.06 +/- 0.00 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0036076
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB097355
KNApSAcK IDC00000857
Chemspider ID9063235
KEGG Compound IDC20230
BioCyc IDCPD-14013
BiGG IDNot Available
Wikipedia LinkSabinene
METLIN IDNot Available
PubChem Compound10887971
PDB IDNot Available
ChEBI ID50029
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 ]
  3. Shulgin AT, Sargent T, Naranjo C: The chemistry and psychopharmacology of nutmeg and of several related phenylisopropylamines. Psychopharmacol Bull. 1967 Dec;4(3):13. [PubMed:5615546 ]
  4. Cao Y, Zhang H, Liu H, Liu W, Zhang R, Xian M, Liu H: Biosynthesis and production of sabinene: current state and perspectives. Appl Microbiol Biotechnol. 2018 Feb;102(4):1535-1544. doi: 10.1007/s00253-017-8695-5. Epub 2017 Dec 20. [PubMed:29264773 ]
  5. Ryu Y, Lee D, Jung SH, Lee KJ, Jin H, Kim SJ, Lee HM, Kim B, Won KJ: Sabinene Prevents Skeletal Muscle Atrophy by Inhibiting the MAPK-MuRF-1 Pathway in Rats. Int J Mol Sci. 2019 Oct 8;20(19). pii: ijms20194955. doi: 10.3390/ijms20194955. [PubMed:31597276 ]