Record Information
Version1.0
Creation date2010-04-08 22:12:12 UTC
Update date2019-11-26 03:12:41 UTC
Primary IDFDB016052
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameCurlone
DescriptionCurlone, also known as b-turmerone, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Curlone is an extremely weak basic (essentially neutral) compound (based on its pKa).
CAS Number87440-60-6
Structure
Thumb
Synonyms
SynonymSource
1,3(15),10-Bisabolatrien-9-oneHMDB
b-TurmeroneHMDB
beta-TurmeroneHMDB
[S-(R*,r*)]-2-methyl-6-(4-methylene-2-cyclohexen-1-yl)-2-hepten-4-oneHMDB
[S-(R*,R*)]-2-Methyl-6-(4-methylene-2-cyclohexen-1-yl)-2-hepten-4-onebiospider
β-turmeronebiospider
Curlonedb_source
Predicted Properties
PropertyValueSource
Water Solubility0.016 g/LALOGPS
logP4.08ALOGPS
logP4.1ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)-4.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity71.17 m³·mol⁻¹ChemAxon
Polarizability26.49 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC15H22O
IUPAC name2-methyl-6-(4-methylidenecyclohex-2-en-1-yl)hept-2-en-4-one
InChI IdentifierInChI=1S/C15H22O/c1-11(2)9-15(16)10-13(4)14-7-5-12(3)6-8-14/h5,7,9,13-14H,3,6,8,10H2,1-2,4H3
InChI KeyJIJQKFPGBBEJNF-UHFFFAOYSA-N
Isomeric SMILESCC(CC(=O)C=C(C)C)C1CCC(=C)C=C1
Average Molecular Weight218.3346
Monoisotopic Molecular Weight218.167065326
Classification
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
  • Bisabolane sesquiterpenoid
  • Sesquiterpenoid
  • Alpha,beta-unsaturated ketone
  • Enone
  • Acryloyl-group
  • Ketone
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 82.52%; H 10.16%; O 7.33%DFC
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -0.03 (c, 2.16 in CHCl3)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9210000000-b2197b6f1a746a9e50a7Spectrum
Predicted GC-MSCurlone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9210000000-b2197b6f1a746a9e50a7Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-1390000000-06976808be91360fa26fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00m3-8930000000-b3cbb70705fc5b1e4b98Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zir-9200000000-c69249db7bf30f834362Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1190000000-ddce2d4b78c32fc7888cSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-066r-9570000000-383af50a796757dd53e6Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9400000000-b9f98bb7b7a39369de54Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-6900000000-91e5d5362ffdcc195202Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000x-9500000000-0f2d03fed0080994ed56Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9100000000-771c6ffd66f137da4ef8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0090000000-868e2fb00a2cfbf6c529Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0159-4940000000-a8b06f9c9198eae9dcafSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9730000000-6fdc3a3050cbcf0e5b2fSpectrum
NMR
TypeDescriptionView
ChemSpider ID170035
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID196216
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB37068
CRC / DFC (Dictionary of Food Compounds) IDLBP73-Q:KMH93-W
EAFUS IDNot Available
Dr. Duke IDCURLONE|BETA-TURMERONE
BIGG IDNot Available
KNApSAcK IDC00011640
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti Alzheimeran52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti cancer35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
cyclooxygenase-2 inhibitor50629 A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.DUKE
iNOS inhibitor23924 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.