Showing Compound Card for 6,10,14-Trimethyl-pentadecan-2-one (CDB000278)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencestransporters (1) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:28:28 UTC
Updated at2020-11-18 16:34:59 UTC
CannabisDB IDCDB000278
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name6,10,14-Trimethyl-pentadecan-2-one
Description6,10,14-trimethyl-Pentadecan-2-one, also known as hexahydrofarnesylacetone, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes that contain 15 carbon atoms with three consecutive 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 ). 6,10,14-trimethyl-Pentadecan-2-one is one of several ketones that are known in cannabis plants (PMID: 6991645 ). 6,10,14-trimethyl-pentadecan-2-one is a celery, fat, and herbal tasting compound and can be found in a number of food items such as sweet basil, common oregano, roselle, and wild celery.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(6R,10R)-6,10,14-Trimethyl-2-pentadecanonePhytoBank
(+)-(R,R)-PhytonePhytoBank
(+)-PhytonePhytoBank
(6R,10R)-6,10,14-Trimethylpentadecan-2-onePhytoBank
(R,R)-PhytonePhytoBank
Phytol ketonePhytoBank
PhytonePhytoBank
6,10,14-Trimethyl-2-pentadecanonePhytoBank
(±)-PhytonePhytoBank
Hexahydrofarnesyl acetonePhytoBank
Perhydrofarnesyl acetonePhytoBank
Chemical FormulaC18H36O
Average Molecular Weight268.49
Monoisotopic Molecular Weight268.2766
IUPAC Name(6R,10R)-6,10,14-trimethylpentadecan-2-one
Traditional Name(6R,10R)-6,10,14-trimethylpentadecan-2-one
CAS Registry NumberNot Available
SMILES
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCCC(C)=O
InChI Identifier
InChI=1S/C18H36O/c1-15(2)9-6-10-16(3)11-7-12-17(4)13-8-14-18(5)19/h15-17H,6-14H2,1-5H3/t16-,17-/m1/s1
InChI KeyWHWDWIHXSPCOKZ-IAGOWNOFSA-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
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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
logP7.48ALOGPS
logP6.56ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)19.64ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity85.08 m³·mol⁻¹ChemAxon
Polarizability36.16 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS6,10,14-Trimethyl-pentadecan-2-one, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS6,10,14-Trimethyl-pentadecan-2-one, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
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
Transporters
Protein NameGene NameLocusUniprot IDDetails
Platelet glycoprotein 4CD367q11.2P16671 details
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
Free fatty acid receptor 1FFAR119q13.1O14842 details
Free fatty acid receptor 4FFAR410q23.33Q5NUL3 details
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 Compound1810793
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. 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 ]
  3. 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 ]

Transporters

Enzyme Details
1. Platelet glycoprotein 4
General function:
Not Available
Specific function:
Seems to have numerous potential physiological functions. Binds to collagen, thrombospondin, anionic phospholipids and oxidized LDL. May function as a cell adhesion molecule. Directly mediates cytoadherence of Plasmodium falciparum parasitized erythrocytes. Binds long chain fatty acids and may function in the transport and/or as a regulator of fatty acid transport
Gene Name:
CD36
Uniprot ID:
P16671
Molecular weight:
53054.0