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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:38 UTC
Update Date2019-01-11 19:40:37 UTC
HMDB IDHMDB0030561
Secondary Accession Numbers
  • HMDB30561
Metabolite Identification
Common Name3-Hydroxy-8,9-dimethoxycoumestan
Description3-Hydroxy-8,9-dimethoxycoumestan is found in alfalfa. 3-Hydroxy-8,9-dimethoxycoumestan is isolated from Medicago sativa (alfalfa) and Myroxylon balsamum (Tolu balsam
Structure
Data?1547235637
Synonyms
ValueSource
7-Hydroxy-11,12-dimethoxycoumestan (obsol.)HMDB
alpha-Ethyl-3-nitrocinnamic acidHMDB
Chemical FormulaC17H12O6
Average Molecular Weight312.2736
Monoisotopic Molecular Weight312.063388116
IUPAC Name5-hydroxy-13,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one
Traditional Name5-hydroxy-13,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one
CAS Registry Number5252-40-4
SMILES
COC1=C(OC)C=C2C(OC3=C2C(=O)OC2=C3C=CC(O)=C2)=C1
InChI Identifier
InChI=1S/C17H12O6/c1-20-13-6-10-12(7-14(13)21-2)22-16-9-4-3-8(18)5-11(9)23-17(19)15(10)16/h3-7,18H,1-2H3
InChI KeyPKLPURDVDNBFCI-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassCoumestans
Direct ParentCoumestans
Alternative Parents
Substituents
  • Furanocoumarin
  • Coumestan
  • Angular furanocoumarin
  • Coumarin
  • 1-benzopyran
  • Benzopyran
  • Furopyran
  • Benzofuran
  • Anisole
  • Pyranone
  • Alkyl aryl ether
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Furan
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point306 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.5ALOGPS
logP2.39ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)7.12ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area78.13 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity80.56 m³·mol⁻¹ChemAxon
Polarizability31.6 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-015a-0091000000-02f30903e7d90b5f517cJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01dl-2319000000-5cb82e5c9d4f5a71a975JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0009000000-7847db498807d288a745JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0019000000-5e0a950b359893c61d69JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0f8a-0090000000-5378a4a24ae0701e7d17JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-c2d8b516decd37e8c92eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0039000000-b23c8cb81c2945a75535JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4j-1090000000-1b31caa06e41bc3396edJSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
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 IDFDB002445
KNApSAcK IDC00009768
Chemspider ID4678016
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5748556
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

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
3-Hydroxy-8,9-dimethoxycoumestan → 6-({13,14-dimethoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-5-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails