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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-17 17:26:47 UTC
Update Date2019-11-12 17:22:30 UTC
HMDB IDHMDB0132723
Secondary Accession NumbersNone
Metabolite Identification
Common Name3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Description3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3-hydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-4-one is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-4-one. It is generated by Dehydroxylase enzyme via a -4p-dehydroxylation-of-substituted-benzene reaction. This -4p-dehydroxylation-of-substituted-benzene occurs in human gut microbiota.
Structure
Data?1563875958
SynonymsNot Available
Chemical FormulaC20H20O10
Average Molecular Weight420.37
Monoisotopic Molecular Weight420.105646844
IUPAC Name3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3-hydroxyphenyl)-2,3-dihydro-1-benzopyran-4-one
CAS Registry NumberNot Available
SMILES
OCC1OC(OC2C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC(O)=CC=C2)C(O)C1O
InChI Identifier
InChI=1S/C20H20O10/c21-7-13-15(25)17(27)20(29-13)30-19-16(26)14-11(24)5-10(23)6-12(14)28-18(19)8-2-1-3-9(22)4-8/h1-6,13,15,17-25,27H,7H2
InChI KeyDIKMWUAYBCDEIJ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavonoid glycosides
Direct ParentFlavonoid-3-O-glycosides
Alternative Parents
Substituents
  • Flavonoid-3-o-glycoside
  • 3'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Flavanone
  • Flavanonol
  • Hydroxyflavonoid
  • Flavan
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Chromane
  • Benzopyran
  • Pentose monosaccharide
  • 1-benzopyran
  • Aryl ketone
  • Aryl alkyl ketone
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Monosaccharide
  • Tetrahydrofuran
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Ether
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Primary alcohol
  • Organic oxide
  • Alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • 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
logP0.45ALOGPS
logP0.98ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)7.75ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area166.14 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity99.08 m³·mol⁻¹ChemAxon
Polarizability40.54 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-00dj-5900014000-3cc8afaca25f06d200c2Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0ab9-9102000000-643f74f1f4188e8ce231Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fe0-0190600000-dcf800335e179dd8e6b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0490000000-2ec892c4d583033570dfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kmr-3930000000-de228cf8a252e595d632Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014r-1150900000-53b1c25dc6ee6ba55866Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0690200000-379a7e1df382c28c7088Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-002o-2920000000-027d3540ce13fdbc1903Spectrum
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 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 Compound131836770
PDB IDNot Available
ChEBI IDNot Available
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 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-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one → [(5-{[5,7-dihydroxy-2-(3-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-3,4-dihydroxyoxolan-2-yl)methoxy]sulfonic aciddetails
3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one → (5-{[5,7-dihydroxy-2-(3-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl)oxidanesulfonic aciddetails
3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one → (2-{[5,7-dihydroxy-2-(3-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-4-hydroxy-5-(hydroxymethyl)oxolan-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-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one → 6-[3-(3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one → 6-[(3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-7-hydroxy-2-(3-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-5-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one → 6-[(3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5-hydroxy-2-(3-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
General function:
sulfotransferase activity
Specific function:
Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:
SULT1A3
Uniprot ID:
P0DMM9
Molecular weight:
34195.96
Reactions
3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-2-(3-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one → [3-(3-{[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-2-yl)phenyl]oxidanesulfonic aciddetails