Showing Compound Card for Alloaromadendrene (CDB000550)

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Record Information
Version1.0
Created at2020-03-19 00:43:11 UTC
Updated at2020-11-18 16:35:16 UTC
CannabisDB IDCDB000550
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameAlloaromadendrene
DescriptionAlloaromadendrene or Aromadendrene belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. Aromadendrene is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpene. Sesquiterpenes 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-erythritol-phosphate (MEP) pathway in the cytosol. 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. Aromadendrene is a neutral, hydrophobic molecule that is largely insoluble in water. It exists as a colorless, clear liquid. Aromadendrene has a woody, musty odor. It is found in a number of plants and spices including allspice, anise fruit, cloves, eucalyptus, ginger, guava, marjoram, oregano, rosemary, sage, thyme and the essential oil of indigenous cinnamon. Alloaromadendrene is also found in cannabis plants, but only in trace amounts (PMID: 6991645 ). Alloaromadendrene appears to exhibit antioxidant activity and has been shown to delay aging in C. elegans (PMID: 24918691 ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC15H24
Average Molecular Weight204.36
Monoisotopic Molecular Weight204.1878
IUPAC Name(1aR,4aS,7R,7aS,7bS)-1,1,7-trimethyl-4-methylidene-decahydro-1H-cyclopropa[e]azulene
Traditional Name(1aR,4aS,7R,7aS,7bS)-1,1,7-trimethyl-4-methylidene-octahydro-1aH-cyclopropa[e]azulene
CAS Registry Number25246-27-9
SMILES
C[C@@H]1CC[C@H]2[C@H]1[C@H]1[C@@H](CCC2=C)C1(C)C
InChI Identifier
InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h10-14H,1,5-8H2,2-4H3/t10-,11-,12-,13+,14-/m1/s1
InChI KeyITYNGVSTWVVPIC-XGFWRYKXSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct Parent5,10-cycloaromadendrane sesquiterpenoids
Alternative Parents
Substituents
  • 5,10-cycloaromadendrane sesquiterpenoid
  • Guaiane sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Ontology
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
logP3.7ALOGPS
logP4.15ChemAxon
logS-4.9ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity64.7 m³·mol⁻¹ChemAxon
Polarizability25.96 ųChemAxon
Number of Rings3ChemAxon
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
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12305247
PDB IDNot Available
ChEBI IDNot Available
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. Yu CW, Li WH, Hsu FL, Yen PL, Chang ST, Liao VH: Essential oil alloaromadendrene from mixed-type Cinnamomum osmophloeum leaves prolongs the lifespan in Caenorhabditis elegans. J Agric Food Chem. 2014 Jul 2;62(26):6159-65. doi: 10.1021/jf500417y. Epub 2014 Jun 23. [PubMed:24918691 ]