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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-16 22:43:13 UTC
Update Date2019-11-12 17:22:14 UTC
HMDB IDHMDB0130166
Secondary Accession NumbersNone
Metabolite Identification
Common Name5,7,8-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
Description5,7,8-trihydroxy-2-(4-hydroxyphenyl)-4h-chromen-4-one is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 5,7,8-trihydroxy-2-(4-methoxyphenyl)-4h-chromen-4-one. It is generated by cyp1a2, cyp2c9, cyp2c19, and cyp2e1 enzymes via an o-dealkylation reaction. This o-dealkylation occurs in humans.
Structure
Data?1563875612
Synonyms
ValueSource
8-HydroxyapigeninChEBI
Chemical FormulaC15H10O6
Average Molecular Weight286.2363
Monoisotopic Molecular Weight286.047738052
IUPAC Name5,7,8-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
Traditional Nameisoscutellarein
CAS Registry NumberNot Available
SMILES
OC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(O)=C(O)C=C2O
InChI Identifier
InChI=1S/C15H10O6/c16-8-3-1-7(2-4-8)12-6-10(18)13-9(17)5-11(19)14(20)15(13)21-12/h1-6,16-17,19-20H
InChI KeyNXHQVROAKYDSNW-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavones. These are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavones
Alternative Parents
Substituents
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • 8-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxygen compound
  • Organic oxide
  • 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
logP2.68ALOGPS
logP2.4ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)6.79ChemAxon
pKa (Strongest Basic)-5.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.89 m³·mol⁻¹ChemAxon
Polarizability27.62 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0l6r-3112290000-36be97f2be2751000469Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-0390000000-539114c70c6fcbbec971Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-6d49fc36ca72b83a9d36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-818288d49bef525615afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02bf-6950000000-ae3693e70ad289722707Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-88a944fe473f85800fefSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0090000000-25e541b13661a4203a52Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01bc-8950000000-b7ddebd79c415ee679f5Spectrum
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 IDNot Available
FooDB IDFDB088984
KNApSAcK IDC00003848
Chemspider IDNot Available
KEGG Compound IDC10097
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIsoscutellarein
METLIN IDNot Available
PubChem Compound5281665
PDB IDNot Available
ChEBI ID6059
Food Biomarker OntologyNot Available
VMH IDNot Available
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
5,7,8-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one → 6-{[7,8-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
5,7,8-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one → 6-{[5,8-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
5,7,8-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one → 3,4,5-trihydroxy-6-[4-(5,7,8-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]oxane-2-carboxylic aciddetails