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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:51:26 UTC
Update Date2022-03-07 02:53:27 UTC
HMDB IDHMDB0032728
Secondary Accession Numbers
  • HMDB32728
Metabolite Identification
Common NameCubebininolide
DescriptionCubebininolide belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety. Cubebininolide has been detected, but not quantified in, herbs and spices. This could make cubebininolide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cubebininolide.
Structure
Data?1563862298
Synonyms
ValueSource
3,3',4,4',5,5'-Hexamethoxylignan-9,9'-olideHMDB
CordigerinHMDB
Chemical FormulaC24H30O8
Average Molecular Weight446.4902
Monoisotopic Molecular Weight446.194067936
IUPAC Name3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one
Traditional Name3,4-bis[(3,4,5-trimethoxyphenyl)methyl]oxolan-2-one
CAS Registry Number93395-16-5
SMILES
COC1=CC(CC2COC(=O)C2CC2=CC(OC)=C(OC)C(OC)=C2)=CC(OC)=C1OC
InChI Identifier
InChI=1S/C24H30O8/c1-26-18-9-14(10-19(27-2)22(18)30-5)7-16-13-32-24(25)17(16)8-15-11-20(28-3)23(31-6)21(12-15)29-4/h9-12,16-17H,7-8,13H2,1-6H3
InChI KeyVUNCHONBJWJYID-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as dibenzylbutyrolactone lignans. These are lignan compounds containing a 3,4-dibenzyloxolan-2-one moiety.
KingdomOrganic compounds
Super ClassLignans, neolignans and related compounds
ClassFuranoid lignans
Sub ClassTetrahydrofuran lignans
Direct ParentDibenzylbutyrolactone lignans
Alternative Parents
Substituents
  • Dibenzylbutyrolactone
  • Lignan lactone
  • Phenoxy compound
  • Anisole
  • Methoxybenzene
  • Phenol ether
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Gamma butyrolactone
  • Benzenoid
  • Tetrahydrofuran
  • Carboxylic acid ester
  • Lactone
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0066 g/LALOGPS
logP3.55ALOGPS
logP3.27ChemAxon
logS-4.8ALOGPS
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area81.68 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity117.53 m³·mol⁻¹ChemAxon
Polarizability46.65 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+206.27631661259
DarkChem[M-H]-204.52431661259
DeepCCS[M+H]+197.030932474
DeepCCS[M-H]-194.64230932474
DeepCCS[M-2H]-228.57930932474
DeepCCS[M+Na]+203.80830932474
AllCCS[M+H]+207.432859911
AllCCS[M+H-H2O]+204.932859911
AllCCS[M+NH4]+209.732859911
AllCCS[M+Na]+210.332859911
AllCCS[M-H]-212.432859911
AllCCS[M+Na-2H]-213.532859911
AllCCS[M+HCOO]-214.732859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CubebininolideCOC1=CC(CC2COC(=O)C2CC2=CC(OC)=C(OC)C(OC)=C2)=CC(OC)=C1OC5016.1Standard polar33892256
CubebininolideCOC1=CC(CC2COC(=O)C2CC2=CC(OC)=C(OC)C(OC)=C2)=CC(OC)=C1OC3451.9Standard non polar33892256
CubebininolideCOC1=CC(CC2COC(=O)C2CC2=CC(OC)=C(OC)C(OC)=C2)=CC(OC)=C1OC3377.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cubebininolide GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-1950800000-e9e5f9963eea926d90502017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cubebininolide 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 - Cubebininolide 10V, Positive-QTOFsplash10-0002-0021900000-bbb63571bff86a7c6b702016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cubebininolide 20V, Positive-QTOFsplash10-0kvk-0194800000-a4a74d2a684a5850c6fc2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cubebininolide 40V, Positive-QTOFsplash10-052g-0933000000-a7f8c697bed74c1e5a832016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cubebininolide 10V, Negative-QTOFsplash10-0002-0000900000-328eac5fe1ede0d5bff82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cubebininolide 20V, Negative-QTOFsplash10-0f92-0004900000-98fa841bb523d2920f762016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cubebininolide 40V, Negative-QTOFsplash10-00tf-0009100000-7d605958c75cdeb5a68e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cubebininolide 10V, Negative-QTOFsplash10-0002-0000900000-5fa608622ec40428d9bd2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cubebininolide 20V, Negative-QTOFsplash10-01p2-0007900000-38ea091b72df93d571ef2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cubebininolide 40V, Negative-QTOFsplash10-0w29-0229200000-eb35551d191b9a1f0ed92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cubebininolide 10V, Positive-QTOFsplash10-0002-0010900000-6b489a1d120d523bc6e42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cubebininolide 20V, Positive-QTOFsplash10-002b-0251900000-bda7f8dfaa73d58e44522021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cubebininolide 40V, Positive-QTOFsplash10-0kai-0559300000-1465d13312a70a3e82402021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB010689
KNApSAcK IDC00055160
Chemspider ID8156597
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9981005
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .