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Showing Compound alpha-Cedrene (FDB003904)

Record Information
Version1.0
Creation date2010-04-08 22:06:00 UTC
Update date2020-09-17 15:34:49 UTC
Primary IDFDB003904
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namealpha-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.
CAS Number469-61-4
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(-)-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
α-Cedrenebiospider
Cedr-8-enebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.0016 g/LALOGPS
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
Chemical FormulaC15H24
IUPAC name(1S,2R,5S,7S)-2,6,6,8-tetramethyltricyclo[5.3.1.0^{1,5}]undec-8-ene
InChI IdentifierInChI=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
Isomeric SMILES[H][C@@]12CC[C@@H](C)[C@]11C[C@@H](C(C)=CC1)C2(C)C
Average Molecular Weight204.3511
Monoisotopic Molecular Weight204.187800768
Classification
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:

Process

Naturally occurring process:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSalpha-Cedrene, non-derivatized, GC-MS Spectrumsplash10-014l-8900000000-bf26b564b0b20c1d093aSpectrum
Predicted GC-MSalpha-Cedrene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03g1-1900000000-d9586d99c9949bf8088bSpectrum
Predicted GC-MSalpha-Cedrene, 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
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC09630
Pubchem Compound ID6431015
Pubchem Substance IDNot Available
ChEBI ID10216
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDJPR59-Y:JJF32-N
EAFUS IDNot Available
Dr. Duke IDALPHA-CEDRENE|CEDRENE
BIGG IDNot Available
KNApSAcK IDC00003111
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1032351
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
irritantDUKE
perfume48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
cedar
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fresh
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.