Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:13:58 UTC
Update Date2022-03-07 02:53:44 UTC
HMDB IDHMDB0033498
Secondary Accession Numbers
  • HMDB33498
Metabolite Identification
Common NameIsonigerone
DescriptionIsonigerone belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. Based on a literature review very few articles have been published on Isonigerone.
Structure
Data?1563862415
SynonymsNot Available
Chemical FormulaC32H26O10
Average Molecular Weight570.5428
Monoisotopic Molecular Weight570.152597052
IUPAC Name5-hydroxy-10-{5-hydroxy-8,10-dimethoxy-2-methyl-4-oxo-4H-benzo[h]chromen-6-yl}-6,8-dimethoxy-2-methyl-4H-benzo[g]chromen-4-one
Traditional Name5-hydroxy-10-{5-hydroxy-8,10-dimethoxy-2-methyl-4-oxobenzo[h]chromen-6-yl}-6,8-dimethoxy-2-methylbenzo[g]chromen-4-one
CAS Registry NumberNot Available
SMILES
COC1=CC2=C(C(O)=C3C(=O)C=C(C)OC3=C2C2=C(O)C3=C(OC(C)=CC3=O)C3=C2C=C(OC)C=C3OC)C(OC)=C1
InChI Identifier
InChI=1S/C32H26O10/c1-13-7-20(34)28-30(36)25(18-10-16(38-4)12-22(40-6)24(18)31(28)41-13)26-17-9-15(37-3)11-21(39-5)23(17)29(35)27-19(33)8-14(2)42-32(26)27/h7-12,35-36H,1-6H3
InChI KeyCQWZRVPFGYDTKI-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthopyranones. Naphthopyranones are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassNaphthopyrans
Sub ClassNaphthopyranones
Direct ParentNaphthopyranones
Alternative Parents
Substituents
  • Naphthopyranone
  • Chromone
  • 1-naphthol
  • 2-naphthol
  • Benzopyran
  • 1-benzopyran
  • Naphthalene
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • 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 Point330 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0043 g/LALOGPS
logP4.24ALOGPS
logP5.46ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)7.63ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area129.98 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity156.01 m³·mol⁻¹ChemAxon
Polarizability58.96 ųChemAxon
Number of Rings6ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+232.45430932474
DeepCCS[M-H]-230.55830932474
DeepCCS[M-2H]-263.79930932474
DeepCCS[M+Na]+238.11830932474
AllCCS[M+H]+231.532859911
AllCCS[M+H-H2O]+229.632859911
AllCCS[M+NH4]+233.132859911
AllCCS[M+Na]+233.632859911
AllCCS[M-H]-226.132859911
AllCCS[M+Na-2H]-226.832859911
AllCCS[M+HCOO]-227.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IsonigeroneCOC1=CC2=C(C(O)=C3C(=O)C=C(C)OC3=C2C2=C(O)C3=C(OC(C)=CC3=O)C3=C2C=C(OC)C=C3OC)C(OC)=C16848.2Standard polar33892256
IsonigeroneCOC1=CC2=C(C(O)=C3C(=O)C=C(C)OC3=C2C2=C(O)C3=C(OC(C)=CC3=O)C3=C2C=C(OC)C=C3OC)C(OC)=C14502.8Standard non polar33892256
IsonigeroneCOC1=CC2=C(C(O)=C3C(=O)C=C(C)OC3=C2C2=C(O)C3=C(OC(C)=CC3=O)C3=C2C=C(OC)C=C3OC)C(OC)=C15007.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isonigerone,1TMS,isomer #1COC1=CC(OC)=C2C(O[Si](C)(C)C)=C3C(=O)C=C(C)OC3=C(C3=C(O)C4=C(OC(C)=CC4=O)C4=C(OC)C=C(OC)C=C34)C2=C14994.2Semi standard non polar33892256
Isonigerone,1TMS,isomer #2COC1=CC(OC)=C2C(O)=C3C(=O)C=C(C)OC3=C(C3=C(O[Si](C)(C)C)C4=C(OC(C)=CC4=O)C4=C(OC)C=C(OC)C=C34)C2=C15017.6Semi standard non polar33892256
Isonigerone,2TMS,isomer #1COC1=CC(OC)=C2C(O[Si](C)(C)C)=C3C(=O)C=C(C)OC3=C(C3=C(O[Si](C)(C)C)C4=C(OC(C)=CC4=O)C4=C(OC)C=C(OC)C=C34)C2=C14841.7Semi standard non polar33892256
Isonigerone,1TBDMS,isomer #1COC1=CC(OC)=C2C(O[Si](C)(C)C(C)(C)C)=C3C(=O)C=C(C)OC3=C(C3=C(O)C4=C(OC(C)=CC4=O)C4=C(OC)C=C(OC)C=C34)C2=C15139.7Semi standard non polar33892256
Isonigerone,1TBDMS,isomer #2COC1=CC(OC)=C2C(O)=C3C(=O)C=C(C)OC3=C(C3=C(O[Si](C)(C)C(C)(C)C)C4=C(OC(C)=CC4=O)C4=C(OC)C=C(OC)C=C34)C2=C15150.7Semi standard non polar33892256
Isonigerone,2TBDMS,isomer #1COC1=CC(OC)=C2C(O[Si](C)(C)C(C)(C)C)=C3C(=O)C=C(C)OC3=C(C3=C(O[Si](C)(C)C(C)(C)C)C4=C(OC(C)=CC4=O)C4=C(OC)C=C(OC)C=C34)C2=C15223.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isonigerone GC-MS (Non-derivatized) - 70eV, Positivesplash10-052f-0000090000-6b618df2218274dc9f492017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isonigerone GC-MS (1 TMS) - 70eV, Positivesplash10-004i-2000069000-313c71ebe0372915596e2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isonigerone GC-MS ("Isonigerone,1TMS,#1" TMS) - 70eV, PositiveNot Available2021-10-14Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isonigerone GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isonigerone GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isonigerone GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isonigerone GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isonigerone GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-10-15Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isonigerone 10V, Positive-QTOFsplash10-00di-0000090000-1f1e2b270cf2b60eba102015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isonigerone 20V, Positive-QTOFsplash10-0fki-0000090000-f8779ba1168344f032782015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isonigerone 40V, Positive-QTOFsplash10-05vk-0000690000-1172c03afaf8dd4915572015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isonigerone 10V, Negative-QTOFsplash10-014i-0000090000-e3a63a894161036df1762015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isonigerone 20V, Negative-QTOFsplash10-0gb9-0000090000-374834fd1633bff2d7522015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isonigerone 40V, Negative-QTOFsplash10-00di-1000590000-b775b3f21e72d305ed442015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isonigerone 10V, Positive-QTOFsplash10-00di-0000090000-19d2aaec626c05e425d82021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isonigerone 20V, Positive-QTOFsplash10-00di-0000090000-80fd1f0a608d2482691a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isonigerone 40V, Positive-QTOFsplash10-0a4r-0000490000-26225eebb9a0027617f02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isonigerone 10V, Negative-QTOFsplash10-014i-0000090000-d0c1e2d0c0af858f93c72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isonigerone 20V, Negative-QTOFsplash10-014i-0000090000-d0c1e2d0c0af858f93c72021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isonigerone 40V, Negative-QTOFsplash10-08fr-0000190000-042a50e5566e89e2dcbb2021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart 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 IDFDB011550
KNApSAcK IDNot Available
Chemspider ID30777012
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound101278413
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.. .