Showing Compound Card for beta-Cedrene (CDB000569)

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Record Information
Version1.0
Created at2020-03-19 00:44:16 UTC
Updated at2020-12-07 19:07:32 UTC
CannabisDB IDCDB000569
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namebeta-Cedrene
Descriptionβ-Cedrene, also known as cedrone, is a member of the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiterpenoids with a structure based on the cedrane or the isocedrane skeleton. Isocedrane is a rearranged cedrane arising from the migration of a methyl group from the position 6 to the position 4. Sesquiterpenoides 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. β-Cedrene is a tricyclic molecule based on a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. β-Cedrene is a naturally occurring tricyclic sesquiterpene found in the essential oil of cedar. There are two known cedrene isomers, namely α- and β-cedrene, which differ in the position of a double bond. β-Cedrene has been found in sweet basil and it has also been detected as a volatile component in cannabis plant samples and essential oils (PMID: 6991645 ; PMID: 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(-)-alpha-CedreneChEBI
(1S,2R,5S,7S)-2,6,6,8-Tetramethyltricyclo[5.3.1.0(1,5)]undec-8-eneChEBI
[3R-(3alpha,3Abeta,7beta,8aalpha)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazuleneChEBI
(-)-a-CedreneGenerator
(-)-Α-cedreneGenerator
[3R-(3a,3Abeta,7b,8aalpha)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazuleneGenerator
[3R-(3Α,3abeta,7β,8aalpha)]-2,3,4,7,8,8a-hexahydro-3,6,8,8-tetramethyl-1H-3a,7-methanoazuleneGenerator
a-CedreneGenerator
Α-cedreneGenerator
alpha-CedreneChEBI
beta-CedreneMeSH
CedroneMeSH
CedreneMeSH
Chemical FormulaC15H24
Average Molecular Weight204.35
Monoisotopic Molecular Weight204.1878
IUPAC Name(1S,2R,5S,7S)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undec-8-ene
Traditional Name(1S,2R,5S,7S)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undec-8-ene
CAS Registry Number469-61-4
SMILES
C[C@@H]1CC[C@H]2C(C)(C)[C@H]3C[C@@]12CC=C3C
InChI Identifier
InChI=1S/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h7,11-13H,5-6,8-9H2,1-4H3/t11-,12+,13+,15+/m1/s1
InChI KeyIRAQOCYXUMOFCW-OSFYFWSMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cedrane and isocedrane sesquiterpenoids. These are sesquiternoids with a structure based on the cedrane or the isocedrane skeleton. Cedrane is a tricyclic molecules a 3,6,8,8-tetramethyl-1H-3a,7-methano-azulene moiety. Isocedrane is a rearranged cedrane arising from the migration of methyl group moved from the 6-position to the 4-position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentCedrane and isocedrane sesquiterpenoids
Alternative Parents
Substituents
  • Cedrane 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
Disposition

Route of exposure:

Source:

Biological location:

Role

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
logP5.18ALOGPS
logP4.1ChemAxon
logS-5.1ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.69 m³·mol⁻¹ChemAxon
Polarizability25.63 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSCedarwood oil terpenes, non-derivatized, GC-MS Spectrumsplash10-014l-8900000000-bf26b564b0b20c1d093aSpectrum
Predicted GC-MSCedarwood oil terpenes, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03g1-1900000000-d9586d99c9949bf8088bSpectrum
Predicted GC-MSCedarwood oil terpenes, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0190000000-cd7b7bd3ccd75e24c49b2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0690000000-5c3400f19be2d725de042017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f9i-9800000000-6baec4093195d46de24a2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-6589dee75f8602eecab52017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-1b2a943b4a7f32ee7b6f2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f79-1920000000-80c16a78fccc89798b3d2017-10-06View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-bfe3306c5c32cdb9f0282021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0w29-0980000000-7697f0bed333d272bce22021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-3910000000-cd4b988301c3693d423b2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0090000000-19077c1e88a70668273f2021-09-24View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0059695
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003904
KNApSAcK IDC00003111
Chemspider ID4936353
KEGG Compound IDC09630
BioCyc IDCPD-8776
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6431015
PDB IDNot Available
ChEBI ID10216
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. 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 ]
  4. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]