Showing Compound Card for Eicosane (CDB000157)

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Record Information
Version1.0
Created at2020-03-18 23:26:54 UTC
Updated at2020-11-18 16:34:51 UTC
CannabisDB IDCDB000157
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameEicosane
DescriptionEicosane, also called icosane, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CH3-[CH2]18-CH3, and consist entirely of hydrogen atoms and saturated carbon atoms. Eeicosane is a hydrocarbon lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. Eicosane has an alkane, and a colorless and waxy taste. It is found in highest concentrations in lemon balms. Eicosane has also been detected in allspices, papaya, coconuts, lindens, and hyssops. This could make eicosane a potential biomarker for the consumption of these foods. Eicosane is also found in cannabis plants (PMID: 6991645 ). Eicosane was associated with Parkinson's disease (PMID: 31041379 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CH3-[CH2]18-CH3ChEBI
N-EicosaneChEBI
OctyldodecaneChEBI
IcosaneHMDB
EicosaneChEBI
Chemical FormulaC20H42
Average Molecular Weight282.55
Monoisotopic Molecular Weight282.3287
IUPAC Nameicosane
Traditional Nameeicosane
CAS Registry Number112-95-8
SMILES
CCCCCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C20H42/c1-3-5-7-9-11-13-15-17-19-20-18-16-14-12-10-8-6-4-2/h3-20H2,1-2H3
InChI KeyCBFCDTFDPHXCNY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms.
KingdomOrganic compounds
Super ClassHydrocarbons
ClassSaturated hydrocarbons
Sub ClassAlkanes
Direct ParentAlkanes
Alternative ParentsNot Available
Substituents
  • Acyclic alkane
  • Alkane
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point36 to 38 °CWikipedia
Boiling Point343.1 °CWikipedia
Water SolubilityNot AvailableNot Available
logP10.897Wikipedia
Predicted Properties
PropertyValueSource
logP9.78ALOGPS
logP9.36ChemAxon
logS-7.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity93.82 m³·mol⁻¹ChemAxon
Polarizability41.94 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0abc-9100000000-b92ea993ede560d3e2642015-03-01View Spectrum
GC-MSEicosane, non-derivatized, GC-MS Spectrumsplash10-00dr-9200000000-8803c91354a1f4960a85Spectrum
GC-MSEicosane, non-derivatized, GC-MS Spectrumsplash10-0a4l-9000000000-e134070d5bd2cd5dee70Spectrum
GC-MSEicosane, non-derivatized, GC-MS Spectrumsplash10-0a4l-9000000000-1fd25ca00429cf4bd43dSpectrum
GC-MSEicosane, non-derivatized, GC-MS Spectrumsplash10-001i-0190000000-81b5d2ec93cf739de33dSpectrum
GC-MSEicosane, non-derivatized, GC-MS Spectrumsplash10-00dr-9200000000-8803c91354a1f4960a85Spectrum
Predicted GC-MSEicosane, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01oy-7930000000-a5a9b082673eeafa59fdSpectrum
Predicted GC-MSEicosane, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0059909
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB004727
KNApSAcK IDNot Available
Chemspider ID7929
KEGG Compound IDNot Available
BioCyc IDCPD-14231
BiGG IDNot Available
Wikipedia LinkIcosane
METLIN IDNot Available
PubChem Compound8222
PDB IDLFA
ChEBI ID43619
References
General References
  1. Trivedi DK, Sinclair E, Xu Y, Sarkar D, Walton-Doyle C, Liscio C, Banks P, Milne J, Silverdale M, Kunath T, Goodacre R, Barran P: Discovery of Volatile Biomarkers of Parkinson's Disease from Sebum. ACS Cent Sci. 2019 Apr 24;5(4):599-606. doi: 10.1021/acscentsci.8b00879. Epub 2019 Mar 20. [PubMed:31041379 ]
  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 ]