Survey with prize
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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-16 04:59:45 UTC
Update Date2019-11-12 17:21:40 UTC
HMDB IDHMDB0128587
Secondary Accession NumbersNone
Metabolite Identification
Common Name5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
Description5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one, also known as 6-hydroxyapigenin or isocarthamidin, 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). Thus, 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one is considered to be a flavonoid lipid molecule. 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one has been detected, but not quantified in, winter savories. This could make 5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one a potential biomarker for the consumption of these foods. Flavone substituted with hydroxy groups at C-4', -5, -6 and -7.
Structure
Data?1563875406
Synonyms
ValueSource
4',5,6,7-TetrahydroxyflavanoneChEBI
5,6,7,4'-TetrahydroxyflavoneChEBI
5,6,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-oneChEBI
6-HydroxyapigeninChEBI
IsocarthamidinChEBI
4',5,6,7-Tetrahydroxy-flavanoneMeSH
6-Hydroxy-apigeninMeSH
Chemical FormulaC15H10O6
Average Molecular Weight286.2363
Monoisotopic Molecular Weight286.047738052
IUPAC Name5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one
Traditional Namescutellarein
CAS Registry NumberNot Available
SMILES
OC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C=C(O)C(O)=C2O
InChI Identifier
InChI=1S/C15H10O6/c16-8-3-1-7(2-4-8)11-5-9(17)13-12(21-11)6-10(18)14(19)15(13)20/h1-6,16,18-20H
InChI KeyJVXZRQGOGOXCEC-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
  • 6-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavone
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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
logP2.74ALOGPS
logP2.4ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)6.75ChemAxon
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
Polarizability27.73 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 (Non-derivatized) - 70eV, Positivesplash10-0aor-0590000000-6c902a6905382235d4e0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0l6r-3304190000-ed90b0d8e1697e6ad54cSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0w29-0119005000-c793e997a188821d0f59Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-00kr-0950000000-2a9ad8450a74a9138db7Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 6V, Negativesplash10-00kr-0950000000-2a9ad8450a74a9138db7Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-000i-0090000000-dfb81d7bffac0efa5dd2Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-000i-0090000000-dfb81d7bffac0efa5dd2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-8d7ea4f4ec2d7b4f1d14Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0190000000-7b9d9b850e6da6eeeafbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02or-3950000000-f9ad546407391419e238Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-4ac71ddb7e307709dad6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0190000000-0c95eb49eb0318e4b526Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00xr-3930000000-5c4e473404a930599809Spectrum
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 ID280
FooDB IDFDB021711
KNApSAcK IDC00003834
Chemspider ID4445014
KEGG Compound IDC10184
BioCyc IDCPD-12726
BiGG IDNot Available
Wikipedia LinkScutellarein
METLIN IDNot Available
PubChem Compound5281697
PDB IDNot Available
ChEBI ID9062
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
5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one → 6-{[5,6-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one → 6-{[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-6-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one → 6-{[6,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-chromen-5-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
5,6,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one → 3,4,5-trihydroxy-6-[4-(5,6,7-trihydroxy-4-oxo-4H-chromen-2-yl)phenoxy]oxane-2-carboxylic aciddetails