Showing Compound Card for (+)-calarene (CDB000482)

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Record Information
Version1.0
Created at2020-03-19 00:39:20 UTC
Updated at2020-12-07 19:07:27 UTC
CannabisDB IDCDB000482
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(+)-calarene
Description(+)-Calarene or Calarene belongs to the class of organic compounds known as aristolane sesquiterpenoids. These are sesquiterpenoids with a structure based on the aristolane skeleton. Aristolanes arise from the C6, C11 cyclization of the bicyclic eremophilane skeleton. 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. It was identified in the essential oil of leaves of Rhododendron aureum (rosebay) (10.4% - 66.4% relative to total oil constituents) (DOI: 10.2298/JSC1002209O), the essential oil from Valeriana jatamansi Jones (Indian valerian or Tagar) (DOI: 10.1080/10412905.2013.767757), the essential oil from Humulus lupulus (hop) (PMID: 24152289 ), the essential oil of Piper sarmentosum (wild pepper) (0.81%) (DOI: 10.1016/S2095-3119(17)61693-9), agarwood oil (24.7% relative to total volatile compounds), spikenard (PMID: 18404340 ), and cannabis (PMID: 26657499 ). It has been shown to have a sedative effect (PMID: 18404340 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
SynonymsNot Available
Chemical FormulaC15H24
Average Molecular Weight204.36
Monoisotopic Molecular Weight204.1878
IUPAC Name(1aR,7S,7aS,7bR)-1,1,7,7a-tetramethyl-1H,1aH,2H,3H,5H,6H,7H,7aH,7bH-cyclopropa[a]naphthalene
Traditional Name(1aR,7S,7aS,7bR)-1,1,7,7a-tetramethyl-1aH,2H,3H,5H,6H,7H,7bH-cyclopropa[a]naphthalene
CAS Registry NumberNot Available
SMILES
C[C@H]1CCC=C2CC[C@@H]3[C@H](C3(C)C)[C@]12C
InChI Identifier
InChI=1S/C15H24/c1-10-6-5-7-11-8-9-12-13(14(12,2)3)15(10,11)4/h7,10,12-13H,5-6,8-9H2,1-4H3/t10-,12+,13+,15+/m0/s1
InChI KeyMBIPADCEHSKJDQ-XTWPYSKKSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.58ALOGPS
logP4.1ChemAxon
logS-5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.69 m³·mol⁻¹ChemAxon
Polarizability25.86 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 CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Van Opstaele F, Praet T, Aerts G, De Cooman L: Characterization of novel single-variety oxygenated sesquiterpenoid hop oil fractions via headspace solid-phase microextraction and gas chromatography-mass spectrometry/olfactometry. J Agric Food Chem. 2013 Nov 6;61(44):10555-64. doi: 10.1021/jf402496t. Epub 2013 Oct 23. [PubMed:24152289 ]
  2. Takemoto H, Ito M, Shiraki T, Yagura T, Honda G: Sedative effects of vapor inhalation of agarwood oil and spikenard extract and identification of their active components. J Nat Med. 2008 Jan;62(1):41-6. doi: 10.1007/s11418-007-0177-0. Epub 2007 Aug 23. [PubMed:18404340 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]