Showing Compound Card for Gamma-Muurolene (CDB000471)

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Record Information
Version1.0
Created at2020-03-19 00:38:43 UTC
Updated at2020-11-18 16:35:11 UTC
CannabisDB IDCDB000471
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameGamma-Muurolene
DescriptionGamma-Muurolene, also known as muurolene, belongs to the class of organic compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ). Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. These are terpenes with three consecutive isoprene units. Gamma-muurolene is possibly neutral and it is one of the terpenes found in the essential oils of the different hemp variaties (DOI: 10.1007/978-1-59259-947-9_2). It was also identified in the essential oil of Artemisia pedemontana (Dwarf Wormwood) (1.6% relative to total volatile compounds) (DOI: 10.1016/S0305-1978(02)00082-0), the seed pod resin of Hymenaea courbaril (stinkingtoe) (DOI: 10.1016/j.jep.2017.05.024), the essential oil from Ocimum gratissimum (clove basil) leaves (11.6% relative to total oil compounds) (PMID: 29578062 ), the essential oil from Cleome droserifolia (spider flower) (4.10% relative to the total oil components) (PMID: 30253077 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(1S,4AS,8ar)-1-isopropyl-7-methyl-4-methylene-1,2,3,4,4a,5,6,8a-octahydronaphthaleneChEBI
(+)-gamma-MuuroleneKegg
(+)-g-MuuroleneGenerator
(+)-Γ-muuroleneGenerator
g-MuuroleneGenerator
Γ-muuroleneGenerator
Chemical FormulaC15H24
Average Molecular Weight204.36
Monoisotopic Molecular Weight204.1878
IUPAC Name(1S,4aS,8aR)-7-methyl-4-methylidene-1-(propan-2-yl)-1,2,3,4,4a,5,6,8a-octahydronaphthalene
Traditional Name(4S,4aR,8aS)-4-isopropyl-6-methyl-1-methylidene-3,4,4a,7,8,8a-hexahydro-2H-naphthalene
CAS Registry NumberNot Available
SMILES
CC(C)[C@@H]1CCC(=C)[C@H]2CCC(C)=C[C@@H]12
InChI Identifier
InChI=1S/C15H24/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h9-10,13-15H,4-8H2,1-3H3/t13-,14+,15-/m0/s1
InChI KeyWRHGORWNJGOVQY-ZNMIVQPWSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Sesquiterpenoid
  • Cadinane sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • 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
logP4.48ALOGPS
logP4.51ChemAxon
logS-4.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.53 m³·mol⁻¹ChemAxon
Polarizability26.2 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.11 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.15 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.07 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.08 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.06 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC20273
BioCyc IDCPD-8791
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12313020
PDB IDNot Available
ChEBI ID64798
References
General References
  1. Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. [PubMed:19932496 ]
  2. Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. [PubMed:17710406 ]
  3. Chimnoi N, Reuk-Ngam N, Chuysinuan P, Khlaychan P, Khunnawutmanotham N, Chokchaichamnankit D, Thamniyom W, Klayraung S, Mahidol C, Techasakul S: Characterization of essential oil from Ocimum gratissimum leaves: Antibacterial and mode of action against selected gastroenteritis pathogens. Microb Pathog. 2018 May;118:290-300. doi: 10.1016/j.micpath.2018.03.041. Epub 2018 Mar 22. [PubMed:29578062 ]
  4. Abd El-Gawad AM, El-Amier YA, Bonanomi G: Essential Oil Composition, Antioxidant and Allelopathic Activities of Cleome droserifolia (Forssk.) Delile. Chem Biodivers. 2018 Dec;15(12):e1800392. doi: 10.1002/cbdv.201800392. Epub 2018 Nov 27. [PubMed:30253077 ]