Gardenin B (CHEM024826)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 21:57:08 UTC
Update Date2016-11-09 01:17:57 UTC
Accession NumberCHEM024826
Identification
Common NameGardenin B
ClassSmall Molecule
DescriptionA tetramethoxyflavone that is tangeretin in which the methoxy group at position 5 has been replaced by a hydroxy group.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5-Hydroxy-2-(4-methoxyphenyl)-6,7,8-trimethoxy-4H-1-benzopyran-4-oneChEBI
5-Hydroxy-4',6,7,8-tetramethoxyflavoneChEBI
DemethyltangeretinChEBI
5-DemethyltangeretinMeSH
Chemical FormulaC19H18O7
Average Molecular Mass358.342 g/mol
Monoisotopic Mass358.105 g/mol
CAS Registry Number2798-20-1
IUPAC Name5-hydroxy-6,7,8-trimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one
Traditional Namegardenin B
SMILESCOC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2O
InChI IdentifierInChI=1S/C19H18O7/c1-22-11-7-5-10(6-8-11)13-9-12(20)14-15(21)17(23-2)19(25-4)18(24-3)16(14)26-13/h5-9,21H,1-4H3
InChI KeyLXEVSYZNYDZSOB-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent8-O-methylated flavonoids
Alternative Parents
Substituents
  • 4p-methoxyflavonoid-skeleton
  • 6-methoxyflavonoid-skeleton
  • 8-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • 5-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Phenol ether
  • Anisole
  • Methoxybenzene
  • Phenoxy compound
  • Pyranone
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Ether
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.023 g/LALOGPS
logP3.07ALOGPS
logP2.68ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)9.66ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area83.45 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.8 m³·mol⁻¹ChemAxon
Polarizability36.75 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-94235dbf8f75c99fbd22Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0009000000-927ca53e683bc4ba6953Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-0259000000-dea961e95f28fe0273c2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-86528933f1fb5f6f49bfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0009000000-779d95151f886854293cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01oy-2195000000-06c67f7a540f7657254dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0009000000-9216d00d19e0b6ee7720Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0009000000-e8d30684b099443b2b9dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014u-0369000000-064772e20e1e0bcdf3ccSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0009000000-c2a6e417d0c66429ddb2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0btc-0009000000-3fa5c4168345d9b2222fSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0302154
FooDB IDFDB002752
Phenol Explorer IDNot Available
KNApSAcK IDC00003883
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID87155
ChEBI ID79628
PubChem Compound ID96539
Kegg Compound IDC15109
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=11198823
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=19296377
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23747095
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=25378691