Showing Compound Card for (5Z)-6,10-Dimethylundeca-5,9-dien-2-one (CDB000195)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencestransporters (1) Show 3 proteinsXML
Record Information
Version1.0
Created at2020-03-18 23:28:18 UTC
Updated at2020-12-07 19:07:15 UTC
CannabisDB IDCDB000195
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name(5Z)-6,10-Dimethylundeca-5,9-dien-2-one
DescriptionGeranylacetone or (5Z)-6,10-Dimethylundeca-5,9-dien-2-one, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Geranylacetone is neutral compound with . a citrus, earthy, and fatty taste. Geranylacetone is found in highest concentrations in wild carrots, carrots, and tortilla and in lower concentrations in corns. Geranylacetone has also been detected in figs, lemon grass, garden tomato (var.), tortilla chips, and papaya. This could make geranylacetone a potential biomarker for the consumption of these foods. Geranylacetone is found in cannabis plants (PMID:6991645 ) and is an industrial intermediate in the vitamin E synthesis ( Ref:DOI ).
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(e)-6,10-Dimethyl-5,9-undecadien-2-oneChEBI
(e)-6,10-Dimethylundeca-5,9-dien-2-oneChEBI
trans-GeranylacetoneChEBI
Geranylacetone, (e)-isomerMeSH
Geranyl acetoneMeSH
(5E)-6,10-Dimethyl-5,9-undecadien-2-oneHMDB
(5E)-6,10-Dimethylundeca-5,9-dien-2-oneHMDB
(e)-6,10-Dimethyl-5,9- undecadien-2-oneHMDB
(e)-Geranyl acetoneHMDB
(e)-GeranylacetoneHMDB
6,10-Dimethyl-(5E)-5,9-undecadien-2-oneHMDB
6,10-Dimethyl-(e)-5,9-undecadien-2-oneHMDB
6,10-Dimethyl-5,9-undecadien-2-oneHMDB
6,10-Dimethyl-5,9-undecadien-2-one, (e)HMDB
6,10-Dimethyl-5,9-undecadiene-2-oneHMDB
6,10-Dimethyl-undecadien-2-oneHMDB
6,10-Dimethylundecadien-2-oneHMDB
DihydropseudoiononeHMDB
FEMA 3542HMDB
Geranyl-acetoneHMDB
GeranylacetonHMDB
GeranylgeranylacetoneHMDB
TeprenoneHMDB
trans-2,6-Dimethyl-2,6-undecadien-2-oneHMDB
trans-6,10-Dimethyl-5,9-undecadien-2-oneHMDB
NerylacetoneMeSH
Chemical FormulaC13H22O
Average Molecular Weight194.31
Monoisotopic Molecular Weight194.1671
IUPAC Name(5Z)-6,10-dimethylundeca-5,9-dien-2-one
Traditional Name(5Z)-6,10-dimethylundeca-5,9-dien-2-one
CAS Registry Number3796-70-1
SMILES
CC(C)=CCC\C(C)=C/CCC(C)=O
InChI Identifier
InChI=1S/C13H22O/c1-11(2)7-5-8-12(3)9-6-10-13(4)14/h7,9H,5-6,8,10H2,1-4H3/b12-9-
InChI KeyHNZUNIKWNYHEJJ-XFXZXTDPSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentAcyclic monoterpenoids
Alternative Parents
Substituents
  • Acyclic monoterpenoid
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP4.59ALOGPS
logP3.68ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)19.6ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity63.83 m³·mol⁻¹ChemAxon
Polarizability24.21 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS(5Z)-6,10-Dimethylundeca-5,9-dien-2-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9500000000-c7325d4dbb4acd6664adSpectrum
Predicted GC-MS(5Z)-6,10-Dimethylundeca-5,9-dien-2-one, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-0900000000-22aaf2de71220d323f8c2016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05y1-5900000000-b9793a3c456efd9db5432016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9200000000-0ccb71b516f62ccb19822016-08-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-49a606374f47e6c4e1432016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-2900000000-37d60e4771277898dc212016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9600000000-52911be4f91a2692f60a2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-25f17943b8774c03383e2021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9500000000-dd9588cb1a45fcad5a572021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9800000000-3d775ed45a51f2d2e1d12021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00lv-8900000000-d76105910cff9afee1a62021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05o3-9100000000-f55f74cdbd28a20984b22021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05mo-9000000000-7f74fb997a0002677d592021-09-24View 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 IDC00029336
Chemspider ID1266569
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGeranylacetone
METLIN IDNot Available
PubChem Compound1549778
PDB IDNot Available
ChEBI ID67206
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 ]

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