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Record Information
Version4.0
StatusPredicted
Creation Date2017-09-17 01:31:48 UTC
Update Date2019-11-12 17:22:25 UTC
HMDB IDHMDB0130881
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)-3-methoxybenzene-1,2-diol
Description4-(7-hydroxy-3,4-dihydro-2h-1-benzopyran-3-yl)-3-methoxybenzene-1,2-diol is a predicted metabolite generated by BioTransformer¹ that is produced by the metabolism of 3-(3-hydroxy-2,4-dimethoxyphenyl)-3,4-dihydro-2h-1-benzopyran-7-ol. It is generated by cyp2c9 enzyme via an o-dealkylation reaction. This o-dealkylation occurs in humans.
Structure
Data?1563875706
SynonymsNot Available
Chemical FormulaC16H16O5
Average Molecular Weight288.299
Monoisotopic Molecular Weight288.099773615
IUPAC Name4-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)-3-methoxybenzene-1,2-diol
Traditional Name4-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)-3-methoxybenzene-1,2-diol
CAS Registry NumberNot Available
SMILES
COC1=C(C=CC(O)=C1O)C1COC2=C(C1)C=CC(O)=C2
InChI Identifier
InChI=1S/C16H16O5/c1-20-16-12(4-5-13(18)15(16)19)10-6-9-2-3-11(17)7-14(9)21-8-10/h2-5,7,10,17-19H,6,8H2,1H3
InChI KeyHAAVPVZHNBZDMX-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 2'-o-methylated isoflavonoids. These are isoflavonoids with methoxy groups attached to the C2' atom of the isoflavonoid backbone. Isoflavonoids are natural products derived from 3-phenylchromen-4-one.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassO-methylated isoflavonoids
Direct Parent2'-O-methylated isoflavonoids
Alternative Parents
Substituents
  • 2p-methoxyisoflavonoid-skeleton
  • Isoflavanol
  • Hydroxyisoflavonoid
  • Isoflavan
  • Chromane
  • Benzopyran
  • Methoxyphenol
  • 1-benzopyran
  • Phenoxy compound
  • Anisole
  • Catechol
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • 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
logP2.31ALOGPS
logP2.73ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.46ChemAxon
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area79.15 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity77.4 m³·mol⁻¹ChemAxon
Polarizability29.99 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 (3 TMS) - 70eV, Positivesplash10-001c-0010900000-9aa19e0da4ca88fdb4b6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fki-0890000000-e5b1049b4b33c69ea728Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0960000000-682031715a081c3350cfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0930000000-d8b3cff93930ef937fb5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05fr-4910000000-3febfb9169795bee5036Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0390000000-4ba1209a84cec8e55ceaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-007a-0960000000-2cb1bdbb7ae114190609Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00di-1940000000-fd208486109a1922bfafSpectrum
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 IDFDB089508
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound129685072
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 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
4-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)-3-methoxybenzene-1,2-diol → (±)-Sphaerosindetails
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
4-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)-3-methoxybenzene-1,2-diol → 6-{[3-(3,4-dihydroxy-2-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
4-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)-3-methoxybenzene-1,2-diol → 3,4,5-trihydroxy-6-[6-hydroxy-3-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)-2-methoxyphenoxy]oxane-2-carboxylic aciddetails
4-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)-3-methoxybenzene-1,2-diol → 3,4,5-trihydroxy-6-[2-hydroxy-4-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)-3-methoxyphenoxy]oxane-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
4-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)-3-methoxybenzene-1,2-diol → [6-hydroxy-3-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)-2-methoxyphenyl]oxidanesulfonic aciddetails