You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusPredicted
Creation Date2017-09-17 22:28:45 UTC
Update Date2019-11-12 17:22:46 UTC
HMDB IDHMDB0133543
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-[(3,4-dihydroxyphenyl)methyl]-2,4,6-trihydroxy-2,3-dihydro-1-benzofuran-3-one
Description2-[(3,4-dihydroxyphenyl)methyl]-2,4,6-trihydroxy-2,3-dihydro-1-benzofuran-3-one belongs to the class of organic compounds known as auronols. These are aurone flavonoids in which the pyran ring of the aurone skeleton carries a hydroxyl group at the 2-position. Thus, 2-[(3,4-dihydroxyphenyl)methyl]-2,4,6-trihydroxy-2,3-dihydro-1-benzofuran-3-one is considered to be a flavonoid lipid molecule. 2-[(3,4-dihydroxyphenyl)methyl]-2,4,6-trihydroxy-2,3-dihydro-1-benzofuran-3-one is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563876075
SynonymsNot Available
Chemical FormulaC15H12O7
Average Molecular Weight304.254
Monoisotopic Molecular Weight304.058302726
IUPAC Name2-[(3,4-dihydroxyphenyl)methyl]-2,4,6-trihydroxy-2,3-dihydro-1-benzofuran-3-one
Traditional Namealphitonin
CAS Registry NumberNot Available
SMILES
OC1=CC(O)=C2C(OC(O)(CC3=CC(O)=C(O)C=C3)C2=O)=C1
InChI Identifier
InChI=1S/C15H12O7/c16-8-4-11(19)13-12(5-8)22-15(21,14(13)20)6-7-1-2-9(17)10(18)3-7/h1-5,16-19,21H,6H2
InChI KeyVCLACNNZBMRRES-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as auronols. These are aurone flavonoids in which the pyran ring of the aurone skeleton carries a hydroxyl group at the 2-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassAurone flavonoids
Sub ClassAuronols
Direct ParentAuronols
Alternative Parents
Substituents
  • Auronol
  • Coumaran
  • Benzofuran
  • Catechol
  • Aryl alkyl ketone
  • Aryl ketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Acyloin
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Hemiacetal
  • Ketone
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organooxygen compound
  • Organic oxygen 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
logP0.94ALOGPS
logP2.47ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)7.59ChemAxon
pKa (Strongest Basic)-5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.45 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity75.05 m³·mol⁻¹ChemAxon
Polarizability28.58 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 (5 TMS) - 70eV, Positivesplash10-014i-4090011000-11a60aefb49bb334633fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-0910000000-a9b26ef2c22d0e249fdaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0819000000-ff091f97e7199e04e68bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05fr-2911000000-ee7fb41091c117b5d9e9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00y4-9600000000-23528788c113df472f79Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0109000000-9b6d2680a8fd61611061Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0839000000-683329b31f44d098a6e2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-056r-3910000000-a6210b60e65e2f880d32Spectrum
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 IDFDB090584
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12305769
PDB IDNot Available
ChEBI ID69013
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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
2-[(3,4-dihydroxyphenyl)methyl]-2,4,6-trihydroxy-2,3-dihydro-1-benzofuran-3-one → 2,4,6-trihydroxy-2-[(4-hydroxy-3-methoxyphenyl)methyl]-2,3-dihydro-1-benzofuran-3-onedetails
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
2-[(3,4-dihydroxyphenyl)methyl]-2,4,6-trihydroxy-2,3-dihydro-1-benzofuran-3-one → 3,4,5-trihydroxy-6-{2-hydroxy-5-[(2,4,6-trihydroxy-3-oxo-2,3-dihydro-1-benzofuran-2-yl)methyl]phenoxy}oxane-2-carboxylic aciddetails
2-[(3,4-dihydroxyphenyl)methyl]-2,4,6-trihydroxy-2,3-dihydro-1-benzofuran-3-one → 3,4,5-trihydroxy-6-{2-hydroxy-4-[(2,4,6-trihydroxy-3-oxo-2,3-dihydro-1-benzofuran-2-yl)methyl]phenoxy}oxane-2-carboxylic aciddetails
2-[(3,4-dihydroxyphenyl)methyl]-2,4,6-trihydroxy-2,3-dihydro-1-benzofuran-3-one → 6-({2-[(3,4-dihydroxyphenyl)methyl]-2,6-dihydroxy-3-oxo-2,3-dihydro-1-benzofuran-4-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
2-[(3,4-dihydroxyphenyl)methyl]-2,4,6-trihydroxy-2,3-dihydro-1-benzofuran-3-one → 6-({2-[(3,4-dihydroxyphenyl)methyl]-2,4-dihydroxy-3-oxo-2,3-dihydro-1-benzofuran-6-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
2-[(3,4-dihydroxyphenyl)methyl]-2,4,6-trihydroxy-2,3-dihydro-1-benzofuran-3-one → {2-hydroxy-5-[(2,4,6-trihydroxy-3-oxo-2,3-dihydro-1-benzofuran-2-yl)methyl]phenyl}oxidanesulfonic aciddetails