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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:56:45 UTC
Update Date2022-03-07 02:54:00 UTC
HMDB IDHMDB0034150
Secondary Accession Numbers
  • HMDB34150
Metabolite Identification
Common NameCernuine
DescriptionCernuine belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus). Cernuine has been detected, but not quantified in, citrus and lemons (Citrus limon). This could make cernuine a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cernuine.
Structure
Data?1563862519
Synonyms
ValueSource
4,6-Dihydroxy-2-[(3,4-dihydroxyphenyl)methylene]-3(2H)-benzofuranone, 9ciHMDB
AureusidinHMDB
Chemical FormulaC15H10O6
Average Molecular Weight286.2363
Monoisotopic Molecular Weight286.047738052
IUPAC Name(2E)-2-[(3,4-dihydroxyphenyl)methylidene]-4,6-dihydroxy-2,3-dihydro-1-benzofuran-3-one
Traditional Name(2E)-2-[(3,4-dihydroxyphenyl)methylidene]-4,6-dihydroxy-1-benzofuran-3-one
CAS Registry Number480-70-6
SMILES
OC1=CC(O)=C2C(=O)\C(OC2=C1)=C/C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C15H10O6/c16-8-5-11(19)14-12(6-8)21-13(15(14)20)4-7-1-2-9(17)10(18)3-7/h1-6,16-19H/b13-4+
InChI KeyWBEFUVAYFSOUEA-YIXHJXPBSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aurone flavonoids. These are flavonoids containing a 2-Benzylidene-1-benzofuran-3-one based core. Aurone flavonoids provide the bright yellow color of some important ornamental flowers, such as snapdragon (Antirrhinum majus).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassAurone flavonoids
Sub ClassNot Available
Direct ParentAurone flavonoids
Alternative Parents
Substituents
  • Aurone
  • Benzofuran
  • Coumaran
  • Catechol
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point295 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.68ALOGPS
logP2.64ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)7.67ChemAxon
pKa (Strongest Basic)-5.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.97 m³·mol⁻¹ChemAxon
Polarizability28.03 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+168.16330932474
DeepCCS[M-H]-165.80530932474
DeepCCS[M-2H]-199.7230932474
DeepCCS[M+Na]+174.94730932474
AllCCS[M+H]+165.532859911
AllCCS[M+H-H2O]+161.732859911
AllCCS[M+NH4]+169.032859911
AllCCS[M+Na]+170.032859911
AllCCS[M-H]-163.732859911
AllCCS[M+Na-2H]-163.032859911
AllCCS[M+HCOO]-162.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CernuineOC1=CC(O)=C2C(=O)\C(OC2=C1)=C/C1=CC(O)=C(O)C=C15165.1Standard polar33892256
CernuineOC1=CC(O)=C2C(=O)\C(OC2=C1)=C/C1=CC(O)=C(O)C=C13089.4Standard non polar33892256
CernuineOC1=CC(O)=C2C(=O)\C(OC2=C1)=C/C1=CC(O)=C(O)C=C13038.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cernuine,1TMS,isomer #1C[Si](C)(C)OC1=CC(O)=C2C(=O)/C(=C\C3=CC=C(O)C(O)=C3)OC2=C13030.3Semi standard non polar33892256
Cernuine,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)/C(=C\C1=CC=C(O)C(O)=C1)O23012.4Semi standard non polar33892256
Cernuine,1TMS,isomer #3C[Si](C)(C)OC1=CC(/C=C2/OC3=CC(O)=CC(O)=C3C2=O)=CC=C1O3012.9Semi standard non polar33892256
Cernuine,1TMS,isomer #4C[Si](C)(C)OC1=CC=C(/C=C2/OC3=CC(O)=CC(O)=C3C2=O)C=C1O3028.9Semi standard non polar33892256
Cernuine,2TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C(=O)/C(=C\C3=CC=C(O)C(O)=C3)O2)C(O[Si](C)(C)C)=C12964.9Semi standard non polar33892256
Cernuine,2TMS,isomer #2C[Si](C)(C)OC1=CC(O)=C2C(=O)/C(=C\C3=CC=C(O[Si](C)(C)C)C(O)=C3)OC2=C13081.6Semi standard non polar33892256
Cernuine,2TMS,isomer #3C[Si](C)(C)OC1=CC(O)=C2C(=O)/C(=C\C3=CC=C(O)C(O[Si](C)(C)C)=C3)OC2=C13075.1Semi standard non polar33892256
Cernuine,2TMS,isomer #4C[Si](C)(C)OC1=CC=C(/C=C2/OC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O3010.3Semi standard non polar33892256
Cernuine,2TMS,isomer #5C[Si](C)(C)OC1=CC(/C=C2/OC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)=CC=C1O2990.6Semi standard non polar33892256
Cernuine,2TMS,isomer #6C[Si](C)(C)OC1=CC=C(/C=C2/OC3=CC(O)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C2979.4Semi standard non polar33892256
Cernuine,3TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C(=O)/C(=C\C3=CC=C(O[Si](C)(C)C)C(O)=C3)O2)C(O[Si](C)(C)C)=C13051.0Semi standard non polar33892256
Cernuine,3TMS,isomer #2C[Si](C)(C)OC1=CC2=C(C(=O)/C(=C\C3=CC=C(O)C(O[Si](C)(C)C)=C3)O2)C(O[Si](C)(C)C)=C13021.7Semi standard non polar33892256
Cernuine,3TMS,isomer #3C[Si](C)(C)OC1=CC(O)=C2C(=O)/C(=C\C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)OC2=C13027.4Semi standard non polar33892256
Cernuine,3TMS,isomer #4C[Si](C)(C)OC1=CC=C(/C=C2/OC3=CC(O)=CC(O[Si](C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C2945.0Semi standard non polar33892256
Cernuine,4TMS,isomer #1C[Si](C)(C)OC1=CC2=C(C(=O)/C(=C\C3=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C3)O2)C(O[Si](C)(C)C)=C13029.8Semi standard non polar33892256
Cernuine,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)/C(=C\C3=CC=C(O)C(O)=C3)OC2=C13291.3Semi standard non polar33892256
Cernuine,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC2=C1C(=O)/C(=C\C1=CC=C(O)C(O)=C1)O23292.4Semi standard non polar33892256
Cernuine,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(/C=C2/OC3=CC(O)=CC(O)=C3C2=O)=CC=C1O3285.3Semi standard non polar33892256
Cernuine,1TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C2/OC3=CC(O)=CC(O)=C3C2=O)C=C1O3296.2Semi standard non polar33892256
Cernuine,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)/C(=C\C3=CC=C(O)C(O)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C13498.2Semi standard non polar33892256
Cernuine,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)/C(=C\C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)OC2=C13561.4Semi standard non polar33892256
Cernuine,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)/C(=C\C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C13561.4Semi standard non polar33892256
Cernuine,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C2/OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O3542.9Semi standard non polar33892256
Cernuine,2TBDMS,isomer #5CC(C)(C)[Si](C)(C)OC1=CC(/C=C2/OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)=CC=C1O3527.6Semi standard non polar33892256
Cernuine,2TBDMS,isomer #6CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C2/OC3=CC(O)=CC(O)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C3491.2Semi standard non polar33892256
Cernuine,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)/C(=C\C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C13825.8Semi standard non polar33892256
Cernuine,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)/C(=C\C3=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C13814.7Semi standard non polar33892256
Cernuine,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC(O)=C2C(=O)/C(=C\C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)OC2=C13759.0Semi standard non polar33892256
Cernuine,3TBDMS,isomer #4CC(C)(C)[Si](C)(C)OC1=CC=C(/C=C2/OC3=CC(O)=CC(O[Si](C)(C)C(C)(C)C)=C3C2=O)C=C1O[Si](C)(C)C(C)(C)C3726.0Semi standard non polar33892256
Cernuine,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC2=C(C(=O)/C(=C\C3=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C3)O2)C(O[Si](C)(C)C(C)(C)C)=C14022.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cernuine GC-MS (Non-derivatized) - 70eV, Positivesplash10-0abi-0590000000-60fdd1319931a92de30e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cernuine GC-MS (4 TMS) - 70eV, Positivesplash10-0nt9-3340190000-3606f26744a113b986b82017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cernuine 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 - Cernuine 10V, Positive-QTOFsplash10-000i-0190000000-3224cb2e84a595e2b3402016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cernuine 20V, Positive-QTOFsplash10-0udr-0890000000-c05de1376c18f593bf582016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cernuine 40V, Positive-QTOFsplash10-0k9i-3910000000-e8808b7a3e9006b5469c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cernuine 10V, Negative-QTOFsplash10-000i-0090000000-fdb1d3719d99503795db2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cernuine 20V, Negative-QTOFsplash10-000i-0190000000-610762391e234975806c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cernuine 40V, Negative-QTOFsplash10-014u-4980000000-43383fa8b2882e1be4472016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cernuine 10V, Negative-QTOFsplash10-000i-0090000000-3713e1ac18e8a67ad4542021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cernuine 20V, Negative-QTOFsplash10-000i-0190000000-f58ff6de88c9e453912e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cernuine 40V, Negative-QTOFsplash10-0uxr-1290000000-99b520f618454ff3673c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cernuine 10V, Positive-QTOFsplash10-000i-0090000000-ad6070afb384abda8f3b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cernuine 20V, Positive-QTOFsplash10-000i-0490000000-67faeaa5bc025bc62ebb2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cernuine 40V, Positive-QTOFsplash10-016r-2390000000-5c2e59ba741b86d4337b2021-09-24Wishart 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 IDFDB012432
KNApSAcK IDC00008027
Chemspider ID11284214
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6123196
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.. .