Showing Compound Card for delta4-carene (CDB000292)

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Record Information
Version1.0
Created at2020-03-19 00:29:18 UTC
Updated at2020-11-18 16:35:00 UTC
CannabisDB IDCDB000292
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namedelta4-carene
DescriptionDelta-4-Carene or (+)-4-Carene, or simply 4-Carene, belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Delta4-Carene is also classified as a cycloalkene (with molecular formula of C10H16) although it is biochemically a monoterpenoid as it synthesized via multiple isoprene units. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID: 7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. There are several isomers of Carene, including Delta-2-Carene, Delta-3-Carene and Delta-4-Carene. Delta-4-Carene is a hydrophobic, neutral molecule that is insoluble in water. Delta-4-Carene has been detected, but not quantified in rosemary, black currants and as a volatile component in tomatoes (PMID: 24096821 ). It exhibits larvicidal activities and appears to be active against the third stage larvae of mosquitoes that carry malaria, Dengue and filariasis (PMID: 27151483 ). It is one of many terpenes that are found in cannabis plants (PMID: 6991645 ). Delta-4-Carene is one of more than 140 terpenes in cannabis and the combination of these terpenoids produces the skunky, fruity odor characteristic of C. savita.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
SynonymsNot Available
Chemical FormulaC10H16
Average Molecular Weight136.24
Monoisotopic Molecular Weight136.1252
IUPAC Name(1S,4S,6S)-4,7,7-trimethylbicyclo[4.1.0]hept-2-ene
Traditional Name(1S,4S,6S)-4,7,7-trimethylbicyclo[4.1.0]hept-2-ene
CAS Registry NumberNot Available
SMILES
C[C@H]1C[C@H]2[C@H](C=C1)C2(C)C
InChI Identifier
InChI=1S/C10H16/c1-7-4-5-8-9(6-7)10(8,2)3/h4-5,7-9H,6H2,1-3H3/t7-,8+,9+/m1/s1
InChI KeyLGNSZMLHOYDATP-VGMNWLOBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Carane monoterpenoid
  • Bicyclic monoterpenoid
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
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
logP3.46ALOGPS
logP2.85ChemAxon
logS-4.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.99 m³·mol⁻¹ChemAxon
Polarizability17.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
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 Compound90473900
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Fang Y, Jiao X, Xie W, Wang S, Wu Q, Shi X, Chen G, Su Q, Yang X, Pan H, Zhang Y: Tomato yellow leaf curl virus alters the host preferences of its vector Bemisia tabaci. Sci Rep. 2013 Oct 7;3:2876. doi: 10.1038/srep02876. [PubMed:24096821 ]
  2. 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 ]
  3. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  4. Govindarajan M, Rajeswary M, Benelli G: delta-Cadinene, Calarene and .delta-4-Carene from Kadsura heteroclita Essential Oil as Novel Larvicides Against Malaria, Dengue and Filariasis Mosquitoes. Comb Chem High Throughput Screen. 2016;19(7):565-71. doi: 10.2174/1386207319666160506123520. [PubMed:27151483 ]