5-Hydroxyauranetin (CHEM027509)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 23:47:12 UTC
Update Date2016-11-09 01:18:28 UTC
Accession NumberCHEM027509
Identification
Common Name5-Hydroxyauranetin
ClassSmall Molecule
Description5-Hydroxyauranetin is found in citrus. 5-Hydroxyauranetin is a constituent of Citrus aurantium (Seville orange).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
5-Hydroxy-3,6,7,8,4'-pentamethoxyflavoneMeSH
4'-O-MethylcalycopterinHMDB
5-Hydroxy-3,4',6,7,8-pentamethoxyflavoneHMDB
5-Hydroxy-3,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-oneHMDB
Chemical FormulaC20H20O8
Average Molecular Mass388.368 g/mol
Monoisotopic Mass388.116 g/mol
CAS Registry Number50439-46-8
IUPAC Name5-hydroxy-3,6,7,8-tetramethoxy-2-(4-methoxyphenyl)-4H-chromen-4-one
Traditional Name5-hydroxyauranetin
SMILESCOC1=CC=C(C=C1)C1=C(OC)C(=O)C2=C(O)C(OC)=C(OC)C(OC)=C2O1
InChI IdentifierInChI=1S/C20H20O8/c1-23-11-8-6-10(7-9-11)15-17(24-2)13(21)12-14(22)18(25-3)20(27-5)19(26-4)16(12)28-15/h6-9,22H,1-5H3
InChI KeyKBYYZSYVUWCARH-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
  • 8-methoxyflavonoid-skeleton
  • 7-methoxyflavonoid-skeleton
  • 3-methoxyflavonoid-skeleton
  • 4p-methoxyflavonoid-skeleton
  • 6-methoxyflavonoid-skeleton
  • Flavone
  • Hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 3-methoxychromone
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Phenoxy compound
  • Phenol ether
  • Anisole
  • Methoxybenzene
  • Pyranone
  • Alkyl aryl ether
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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 Solubility0.024 g/LALOGPS
logP2.85ALOGPS
logP2.55ChemAxon
logS-4.2ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area92.68 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity101.52 m³·mol⁻¹ChemAxon
Polarizability39.56 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0c00-0029000000-0b0b1129584de508a434Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006t-1113900000-9698c97fe9afa8df2026Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-2341ffcf02e65a34b2f2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0009000000-6b0428350d512781a903Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-0149000000-df93e7184b087c691f26Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-03bb3f948b9f5623b314Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0009000000-563ea13309293448342fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0h9d-3597000000-218db5faabb5dac57ce5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0009000000-035da719ec100ab7be19Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0029000000-3ecefff4a9d34c4d9fc6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ar0-2893000000-931d6cf6529d032e3113Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0009000000-ede85f82b500aeed4a15Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0009000000-5023012497465e1b00caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004r-1094000000-3378917b129e226c96f1Spectrum
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 IDHMDB0033275
FooDB IDFDB011298
Phenol Explorer IDNot Available
KNApSAcK IDC00004673
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID9254772
ChEBI IDNot Available
PubChem Compound ID11079623
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.