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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-16 04:57:38 UTC
Update Date2019-03-07 00:19:27 UTC
HMDB IDHMDB0128581
Secondary Accession NumbersNone
Metabolite Identification
Common Name5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one
Description5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4h-chromen-4-one is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 5,7-dihydroxy-6-methoxy-2-phenyl-4h-chromen-4-one. It is generated by cyp1a2, cyp2b6, cyp2c9, cyp2c19, cyp2d6, and cyp2e1 enzymes via a p-hydroxylation-of-monosubstituted-benzene reaction. This p-hydroxylation-of-monosubstituted-benzene occurs in humans.
Structure
Data?1551917967
Synonyms
ValueSource
4',5,7-Trihydroxy-6-methoxyflavoneChEBI
DinatinChEBI
NSC 122415ChEBI
Scutellarein 6-methyl etherChEBI
Chemical FormulaC16H12O6
Average Molecular Weight300.2629
Monoisotopic Molecular Weight300.063388116
IUPAC Name5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one
Traditional Namehispidulin
CAS Registry NumberNot Available
SMILES
COC1=C(O)C2=C(OC(=CC2=O)C2=CC=C(O)C=C2)C=C1O
InChI Identifier
InChI=1S/C16H12O6/c1-21-16-11(19)7-13-14(15(16)20)10(18)6-12(22-13)8-2-4-9(17)5-3-8/h2-7,17,19-20H,1H3
InChI KeyIHFBPDAQLQOCBX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 6-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C6 atom of the flavonoid backbone.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassO-methylated flavonoids
Direct Parent6-O-methylated flavonoids
Alternative Parents
Substituents
  • 6-methoxyflavonoid-skeleton
  • Hydroxyflavonoid
  • Flavone
  • 7-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • Chromone
  • 1-benzopyran
  • Methoxyphenol
  • Benzopyran
  • Resorcinol
  • Anisole
  • Pyranone
  • Phenol
  • Alkyl aryl ether
  • Benzenoid
  • Pyran
  • Monocyclic benzene moiety
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Source:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.09ALOGPS
logP2.55ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)7.09ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity79.38 m³·mol⁻¹ChemAxon
Polarizability29.85 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fz9-0691000000-934a52a4fdc07cbac97dJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0fdo-3657980000-e4090a3ee8fff8059509JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-03di-0009000000-3392b930c7dbdf6b9413JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-001i-0090000000-4a82ea952bce7ac89d70JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0040-0690000000-5fbad78704cd6c99bdcaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0090000000-5978ba0a9b9e42e72060JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-015i-0920000000-8775d11ac816cea8c962JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0002-0091000000-9cb8af9b78593515a786JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-4578ff253ba85d928847JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0019000000-d8384fad6bb29a3ef02cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00g0-3940000000-150112fe8c4c900b9b20JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-e4345c22385448903e5eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-a8b1c93720db66dd7309JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01dr-1940000000-b25493f984eefa9c1131JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
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 ID268
FoodDB IDFDB001473
KNApSAcK IDNot Available
Chemspider ID4444947
KEGG Compound IDC10058
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHispidulin
METLIN IDNot Available
PubChem Compound5281628
PDB IDNot Available
ChEBI ID75902
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one → 3,4,5-trihydroxy-6-{[5-hydroxy-2-(4-hydroxyphenyl)-6-methoxy-4-oxo-4H-chromen-7-yl]oxy}oxane-2-carboxylic aciddetails
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one → 3,4,5-trihydroxy-6-{[7-hydroxy-2-(4-hydroxyphenyl)-6-methoxy-4-oxo-4H-chromen-5-yl]oxy}oxane-2-carboxylic aciddetails
5,7-dihydroxy-2-(4-hydroxyphenyl)-6-methoxy-4H-chromen-4-one → 6-[4-(5,7-dihydroxy-6-methoxy-4-oxo-4H-chromen-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails