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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-16 15:05:43 UTC
Update Date2019-07-23 09:51:55 UTC
HMDB IDHMDB0129433
Secondary Accession NumbersNone
Metabolite Identification
Common Name3,5,6,7-tetrahydroxy-2-(2,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Description3,5,6,7-tetrahydroxy-2-(2,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-one is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 3,5,6,7-tetrahydroxy-2-(2,4,5-trihydroxyphenyl)-4h-chromen-4-one. It is generated by unspecified-gutmicro enzyme via a flavonoid-c-ring-reduction reaction. This flavonoid-c-ring-reduction occurs in human gut microbiota.
Structure
Data?1563875515
SynonymsNot Available
Chemical FormulaC15H12O9
Average Molecular Weight336.252
Monoisotopic Molecular Weight336.048131966
IUPAC Name3,5,6,7-tetrahydroxy-2-(2,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name3,5,6,7-tetrahydroxy-2-(2,4,5-trihydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one
CAS Registry NumberNot Available
SMILES
OC1C(OC2=C(C(O)=C(O)C(O)=C2)C1=O)C1=CC(O)=C(O)C=C1O
InChI Identifier
InChI=1S/C15H12O9/c16-5-2-7(18)6(17)1-4(5)15-14(23)13(22)10-9(24-15)3-8(19)11(20)12(10)21/h1-3,14-21,23H
InChI KeyFZIGXPBSHXRYDX-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as flavanonols. These are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavanonols
Alternative Parents
Substituents
  • Flavanonol
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 6-hydroxyflavonoid
  • Hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Chromone
  • Benzopyran
  • Chromane
  • 1-benzopyran
  • Hydroxyquinol derivative
  • Aryl alkyl ketone
  • Aryl ketone
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP0.91ALOGPS
logP1.21ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)7.88ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area167.91 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity78.57 m³·mol⁻¹ChemAxon
Polarizability30.75 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 (5 TMS) - 70eV, Positivesplash10-01c0-1351009000-395b934ff8c41db8a73aJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ldr-0914000000-04b5a72c9c8812fa1fd7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0109000000-829ecc44151985673e73JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-0905000000-94e655a9263f8b36075dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v0c-3900000000-ce577c00a7e79099e140JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0219000000-677415370d08645b0550JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0935000000-bd161845b3caf6a1fbcbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00fr-6901000000-a1954b6a11aef2f86280JSpectraViewer | 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 IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI 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 magnesium ion binding
Specific function:
Catalyzes the O-methylation, and thereby the inactivation, of catecholamine neurotransmitters and catechol hormones. Also shortens the biological half-lives of certain neuroactive drugs, like L-DOPA, alpha-methyl DOPA and isoproterenol.
Gene Name:
COMT
Uniprot ID:
P21964
Molecular weight:
30036.77
Reactions
3,5,6,7-tetrahydroxy-2-(2,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one → 2-(2,5-dihydroxy-4-methoxyphenyl)-3,5,6,7-tetrahydroxy-3,4-dihydro-2H-1-benzopyran-4-onedetails
General function:
Involved in sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:
SULT2B1
Uniprot ID:
O00204
Molecular weight:
39598.595
Reactions
3,5,6,7-tetrahydroxy-2-(2,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one → [5,6,7-trihydroxy-4-oxo-2-(2,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3-yl]oxidanesulfonic aciddetails
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
3,5,6,7-tetrahydroxy-2-(2,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one → 6-[4,5-dihydroxy-2-(3,5,6,7-tetrahydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3,5,6,7-tetrahydroxy-2-(2,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one → 6-[2,5-dihydroxy-4-(3,5,6,7-tetrahydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3,5,6,7-tetrahydroxy-2-(2,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one → 6-[2,4-dihydroxy-5-(3,5,6,7-tetrahydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3,5,6,7-tetrahydroxy-2-(2,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one → 3,4,5-trihydroxy-6-{[3,6,7-trihydroxy-4-oxo-2-(2,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-5-yl]oxy}oxane-2-carboxylic aciddetails
3,5,6,7-tetrahydroxy-2-(2,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one → 3,4,5-trihydroxy-6-{[3,5,7-trihydroxy-4-oxo-2-(2,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-6-yl]oxy}oxane-2-carboxylic aciddetails
3,5,6,7-tetrahydroxy-2-(2,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one → 3,4,5-trihydroxy-6-{[3,5,6-trihydroxy-4-oxo-2-(2,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}oxane-2-carboxylic aciddetails