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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:57:56 UTC
Update Date2022-03-07 02:53:38 UTC
HMDB IDHMDB0033252
Secondary Accession Numbers
  • HMDB33252
Metabolite Identification
Common NameCurcumanolide A
DescriptionCurcumanolide A belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. Based on a literature review a small amount of articles have been published on Curcumanolide A.
Structure
Data?1563862376
Synonyms
ValueSource
Curcumanolide aMeSH
Chemical FormulaC15H22O2
Average Molecular Weight234.334
Monoisotopic Molecular Weight234.161979948
IUPAC Name6-methyl-9-(prop-1-en-2-yl)-3-(propan-2-ylidene)-1-oxaspiro[4.4]nonan-2-one
Traditional Name6-methyl-9-(prop-1-en-2-yl)-3-(propan-2-ylidene)-1-oxaspiro[4.4]nonan-2-one
CAS Registry Number97550-04-4
SMILES
CC1CCC(C(C)=C)C11CC(=C(C)C)C(=O)O1
InChI Identifier
InChI=1S/C15H22O2/c1-9(2)12-8-15(17-14(12)16)11(5)6-7-13(15)10(3)4/h11,13H,3,6-8H2,1-2,4-5H3
InChI KeyKHOTZHZBHNDKOB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTerpene lactones
Direct ParentTerpene lactones
Alternative Parents
Substituents
  • Terpene lactone
  • Monoterpenoid
  • Gamma butyrolactone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Tetrahydrofuran
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxide
  • Organooxygen compound
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic 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 Solubility0.12 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP4.2ALOGPS
logP3.86ChemAxon
logS-3.3ALOGPS
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity68.81 m³·mol⁻¹ChemAxon
Polarizability26.99 ųChemAxon
Number of Rings2ChemAxon
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]+158.48431661259
DarkChem[M-H]-152.84331661259
DeepCCS[M-2H]-191.15930932474
DeepCCS[M+Na]+166.67530932474
AllCCS[M+H]+153.132859911
AllCCS[M+H-H2O]+149.332859911
AllCCS[M+NH4]+156.632859911
AllCCS[M+Na]+157.632859911
AllCCS[M-H]-162.232859911
AllCCS[M+Na-2H]-162.432859911
AllCCS[M+HCOO]-162.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Curcumanolide ACC1CCC(C(C)=C)C11CC(=C(C)C)C(=O)O12624.1Standard polar33892256
Curcumanolide ACC1CCC(C(C)=C)C11CC(=C(C)C)C(=O)O11759.2Standard non polar33892256
Curcumanolide ACC1CCC(C(C)=C)C11CC(=C(C)C)C(=O)O11806.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Curcumanolide A GC-MS (Non-derivatized) - 70eV, Positivesplash10-054x-9310000000-2a83bba1f7465fa7711e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Curcumanolide A 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 - Curcumanolide A 10V, Positive-QTOFsplash10-000i-1890000000-ed6316b4d4168d87e16a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumanolide A 20V, Positive-QTOFsplash10-0pvv-7910000000-9d70c08f8f4646589fc82015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumanolide A 40V, Positive-QTOFsplash10-0aou-9100000000-93830766a86ce1c9e7282015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumanolide A 10V, Positive-QTOFsplash10-000i-1890000000-ed6316b4d4168d87e16a2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumanolide A 20V, Positive-QTOFsplash10-0pvv-7910000000-9d70c08f8f4646589fc82015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumanolide A 40V, Positive-QTOFsplash10-0aou-9100000000-93830766a86ce1c9e7282015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumanolide A 10V, Negative-QTOFsplash10-001i-0390000000-233c6b0998928a4fd40b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumanolide A 20V, Negative-QTOFsplash10-001r-1940000000-d57d7cc88fbd310b14da2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumanolide A 40V, Negative-QTOFsplash10-00lr-4900000000-978c8069a257bef96a442015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumanolide A 10V, Negative-QTOFsplash10-001i-0390000000-233c6b0998928a4fd40b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumanolide A 20V, Negative-QTOFsplash10-001r-1940000000-d57d7cc88fbd310b14da2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumanolide A 40V, Negative-QTOFsplash10-00lr-4900000000-978c8069a257bef96a442015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumanolide A 10V, Negative-QTOFsplash10-001i-0090000000-9087f47ed0ae51229a172021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumanolide A 20V, Negative-QTOFsplash10-001i-1290000000-237bf46941e4c15bc92d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumanolide A 40V, Negative-QTOFsplash10-0159-9720000000-a718e6415b4708b4ad5e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumanolide A 10V, Positive-QTOFsplash10-000i-0090000000-f533be15bbc90af7433e2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumanolide A 20V, Positive-QTOFsplash10-009l-9740000000-a3c9cd1970a43b4a249a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Curcumanolide A 40V, Positive-QTOFsplash10-0006-9300000000-09580861724f3359d57b2021-09-22Wishart 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 IDFDB011273
KNApSAcK IDC00055271
Chemspider ID35013565
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound14191393
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1636561
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.