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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 22:18:39 UTC
Update Date2022-03-07 02:55:10 UTC
HMDB IDHMDB0037068
Secondary Accession Numbers
  • HMDB37068
Metabolite Identification
Common NameCurlone
DescriptionCurlone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on Curlone.
Structure
Data?1563862972
Synonyms
ValueSource
1,3(15),10-Bisabolatrien-9-oneHMDB
b-TurmeroneHMDB
beta-TurmeroneHMDB, MeSH
[S-(R*,r*)]-2-methyl-6-(4-methylene-2-cyclohexen-1-yl)-2-hepten-4-oneHMDB
Chemical FormulaC15H22O
Average Molecular Weight218.3346
Monoisotopic Molecular Weight218.167065326
IUPAC Name2-methyl-6-(4-methylidenecyclohex-2-en-1-yl)hept-2-en-4-one
Traditional Name2-methyl-6-(4-methylidenecyclohex-2-en-1-yl)hept-2-en-4-one
CAS Registry Number87440-60-6
SMILES
CC(CC(=O)C=C(C)C)C1CCC(=C)C=C1
InChI Identifier
InChI=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
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
  • 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
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.19 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+153.82531661259
DarkChem[M-H]-152.62331661259
DeepCCS[M+H]+157.15830932474
DeepCCS[M-H]-154.830932474
DeepCCS[M-2H]-187.82730932474
DeepCCS[M+Na]+163.25130932474
AllCCS[M+H]+152.832859911
AllCCS[M+H-H2O]+148.932859911
AllCCS[M+NH4]+156.432859911
AllCCS[M+Na]+157.432859911
AllCCS[M-H]-158.832859911
AllCCS[M+Na-2H]-159.532859911
AllCCS[M+HCOO]-160.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CurloneCC(CC(=O)C=C(C)C)C1CCC(=C)C=C12330.2Standard polar33892256
CurloneCC(CC(=O)C=C(C)C)C1CCC(=C)C=C11655.6Standard non polar33892256
CurloneCC(CC(=O)C=C(C)C)C1CCC(=C)C=C11659.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Curlone,1TMS,isomer #1C=C1C=CC(C(C)C=C(C=C(C)C)O[Si](C)(C)C)CC11891.6Semi standard non polar33892256
Curlone,1TMS,isomer #1C=C1C=CC(C(C)C=C(C=C(C)C)O[Si](C)(C)C)CC11746.3Standard non polar33892256
Curlone,1TBDMS,isomer #1C=C1C=CC(C(C)C=C(C=C(C)C)O[Si](C)(C)C(C)(C)C)CC12105.7Semi standard non polar33892256
Curlone,1TBDMS,isomer #1C=C1C=CC(C(C)C=C(C=C(C)C)O[Si](C)(C)C(C)(C)C)CC11986.3Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Curlone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9210000000-b2197b6f1a746a9e50a72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Curlone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curlone 10V, Positive-QTOFsplash10-014i-1390000000-06976808be91360fa26f2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curlone 20V, Positive-QTOFsplash10-00m3-8930000000-b3cbb70705fc5b1e4b982016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curlone 40V, Positive-QTOFsplash10-0zir-9200000000-c69249db7bf30f8343622016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curlone 10V, Negative-QTOFsplash10-014i-1190000000-ddce2d4b78c32fc7888c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curlone 20V, Negative-QTOFsplash10-066r-9570000000-383af50a796757dd53e62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curlone 40V, Negative-QTOFsplash10-0a4i-9400000000-b9f98bb7b7a39369de542016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curlone 10V, Positive-QTOFsplash10-00di-6900000000-91e5d5362ffdcc1952022021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curlone 20V, Positive-QTOFsplash10-000x-9500000000-0f2d03fed0080994ed562021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curlone 40V, Positive-QTOFsplash10-0006-9100000000-771c6ffd66f137da4ef82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curlone 10V, Negative-QTOFsplash10-014i-0090000000-868e2fb00a2cfbf6c5292021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curlone 20V, Negative-QTOFsplash10-0159-4940000000-a8b06f9c9198eae9dcaf2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curlone 40V, Negative-QTOFsplash10-014i-9730000000-6fdc3a3050cbcf0e5b2f2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB016052
KNApSAcK IDC00011640
Chemspider ID170035
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound196216
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1859061
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.