Showing Compound Card for Neophytadiene (CDB005831)

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Record Information
Version1.0
Created at2020-04-27 17:00:55 UTC
Updated at2021-01-04 18:49:23 UTC
CannabisDB IDCDB005831
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameNeophytadiene
DescriptionNeophytadiene or 7,11,15-trimethyl-3-methylidenehexadec-1-ene, belongs to the class of organic compounds known as diterpenes. Neophytadiene is a hydrophobic, neutral compound. It is formally classified as an unsaturated hydrocarbon although it is biochemically a diterpene as it can be synthesized via isoprene units. Diterpenes are a class of chemical compounds composed of four isoprene units, often with the molecular formula C20H32 (they have 20 carbons). They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being a primary intermediate. Diterpenes form the basis for biologically important compounds such as retinol, retinal, and phytol. They are known to have antimicrobial and anti-inflammatory properties ( Ref:DOI ). Neophytadiene can be isolated from tobacco leaves as a clear, colorless oil ( Ref:DOI ). Neophytadiene is also a constituent of cannabis smoke and is formed during the combustion of cannabis ( Ref:DOI ). Neophytadiene has been shown to exhibit anti-inflammatory activity in rats (PMID:18155865 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-(4,8,12-Trimethyltridecyl)-1,3-butadieneChEBI
2-(4,8,12-Trimethyltridecyl)buta-1,3-dieneChEBI
3-Methylene-7,11,15-trimethyl-1-hexadeceneChEBI
3-Methylene-7,11,15-trimethylhexadec-1-eneChEBI
7,11,15-Trimethyl-3-methylene-1-hexadeceneChEBI
Chemical FormulaC20H38
Average Molecular Weight278.52
Monoisotopic Molecular Weight278.2974
IUPAC Name7,11,15-trimethyl-3-methylidenehexadec-1-ene
Traditional Name7,11,15-trimethyl-3-methylidenehexadec-1-ene
CAS Registry Number504-96-1
SMILES
CC(C)CCCC(C)CCCC(C)CCCC(=C)C=C
InChI Identifier
InChI=1S/C20H38/c1-7-18(4)12-9-14-20(6)16-10-15-19(5)13-8-11-17(2)3/h7,17,19-20H,1,4,8-16H2,2-3,5-6H3
InChI KeyNIDGCIPAMWNKOA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Farsesane sesquiterpenoid
  • Sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Alkadiene
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Acyclic olefin
  • Hydrocarbon
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.12ALOGPS
logP8.07ChemAxon
logS-7ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity93.43 m³·mol⁻¹ChemAxon
Polarizability38.58 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-1290000000-b60b68b6a74bcd9918782016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00b9-7960000000-ac6342519d82051a8cbf2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aor-9310000000-4647ca0ef4bdff68fa3d2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-4dae133571732b43fa6d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-1e829c1fed1cf96d7e772016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-3790000000-33aca52e40b5f50f184d2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-4490000000-319c93d0db3dfaf2d6002021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0c0s-9700000000-2f7821053cd927119bdf2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-9000000000-98c6a8c30304f358e7a72021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0090000000-4111e6bd8bbc57d0b7542021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0090000000-2d3a59cb2c6ae07e078f2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01t9-1690000000-56424b6b820e2675316c2021-10-21View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0302243
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003861
KNApSAcK IDC00022075
Chemspider ID10014
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID145817
References
General References
  1. Carretero ME, Lopez-Perez JL, Abad MJ, Bermejo P, Tillet S, Israel A, Noguera-P B: Preliminary study of the anti-inflammatory activity of hexane extract and fractions from Bursera simaruba (Linneo) Sarg. (Burseraceae) leaves. J Ethnopharmacol. 2008 Feb 28;116(1):11-5. doi: 10.1016/j.jep.2007.10.034. Epub 2007 Oct 30. [PubMed:18155865 ]