Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:37:39 UTC
Update Date2022-03-07 02:52:36 UTC
HMDB IDHMDB0030562
Secondary Accession Numbers
  • HMDB30562
Metabolite Identification
Common Name3,8-Dihydroxy-9-methoxycoumestan
Description3,8-Dihydroxy-9-methoxycoumestan, also known as 8-methoxycoumestrol, 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. Thus, 3,8-dihydroxy-9-methoxycoumestan is considered to be a flavonoid. Based on a literature review very few articles have been published on 3,8-Dihydroxy-9-methoxycoumestan.
Structure
Data?1563862004
Synonyms
ValueSource
3'-Methoxycoumestrol (obsol.)HMDB
8-MethoxycoumestrolHMDB
Chemical FormulaC16H10O6
Average Molecular Weight298.247
Monoisotopic Molecular Weight298.047738052
IUPAC Name5,14-dihydroxy-13-methoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-9-one
Traditional Name3'-methoxycoumestrol
CAS Registry NumberNot Available
SMILES
COC1=C(O)C=C2OC3=C(C2=C1)C(=O)OC1=C3C=CC(O)=C1
InChI Identifier
InChI=1S/C16H10O6/c1-20-13-5-9-12(6-10(13)18)21-15-8-3-2-7(17)4-11(8)22-16(19)14(9)15/h2-6,17-18H,1H3
InChI KeyMQORJFLPGOCLDS-UHFFFAOYSA-N
Chemical Taxonomy
Description 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
  • Coumestan
  • Angular furanocoumarin
  • Furanocoumarin
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Benzofuran
  • Furopyran
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Furan
  • Lactone
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point329 - 329.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.31 g/LALOGPS
logP2.58ALOGPS
logP2.24ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)7.11ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area89.13 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity76.08 m³·mol⁻¹ChemAxon
Polarizability29.47 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+167.9131661259
DarkChem[M-H]-167.531661259
DeepCCS[M+H]+176.37330932474
DeepCCS[M-H]-174.01530932474
DeepCCS[M-2H]-207.81830932474
DeepCCS[M+Na]+183.04630932474
AllCCS[M+H]+166.932859911
AllCCS[M+H-H2O]+163.232859911
AllCCS[M+NH4]+170.332859911
AllCCS[M+Na]+171.332859911
AllCCS[M-H]-168.232859911
AllCCS[M+Na-2H]-167.132859911
AllCCS[M+HCOO]-166.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3,8-Dihydroxy-9-methoxycoumestanCOC1=C(O)C=C2OC3=C(C2=C1)C(=O)OC1=C3C=CC(O)=C14405.1Standard polar33892256
3,8-Dihydroxy-9-methoxycoumestanCOC1=C(O)C=C2OC3=C(C2=C1)C(=O)OC1=C3C=CC(O)=C12911.7Standard non polar33892256
3,8-Dihydroxy-9-methoxycoumestanCOC1=C(O)C=C2OC3=C(C2=C1)C(=O)OC1=C3C=CC(O)=C13127.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3,8-Dihydroxy-9-methoxycoumestan,1TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)OC1=C2C(=O)OC2=CC(O)=CC=C213101.5Semi standard non polar33892256
3,8-Dihydroxy-9-methoxycoumestan,1TMS,isomer #2COC1=CC2=C(C=C1O)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C)=CC=C213228.8Semi standard non polar33892256
3,8-Dihydroxy-9-methoxycoumestan,2TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C)=CC=C213240.0Semi standard non polar33892256
3,8-Dihydroxy-9-methoxycoumestan,1TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)OC1=C2C(=O)OC2=CC(O)=CC=C213312.9Semi standard non polar33892256
3,8-Dihydroxy-9-methoxycoumestan,1TBDMS,isomer #2COC1=CC2=C(C=C1O)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C213434.6Semi standard non polar33892256
3,8-Dihydroxy-9-methoxycoumestan,2TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)OC1=C2C(=O)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C213697.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3,8-Dihydroxy-9-methoxycoumestan GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fza-0090000000-76df4a3bbd5cbf3d35212017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,8-Dihydroxy-9-methoxycoumestan GC-MS (2 TMS) - 70eV, Positivesplash10-01ea-2719400000-827a35e9748bd2ad1b5a2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3,8-Dihydroxy-9-methoxycoumestan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxycoumestan 10V, Positive-QTOFsplash10-0002-0090000000-81ccf2688b5b3be93b6f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxycoumestan 20V, Positive-QTOFsplash10-0002-0090000000-15f1e3c1bb77baa467f82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxycoumestan 40V, Positive-QTOFsplash10-0arr-0090000000-8453f168e3c9246e99522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxycoumestan 10V, Negative-QTOFsplash10-0002-0090000000-3ee8a6990521f9453d7d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxycoumestan 20V, Negative-QTOFsplash10-0002-0090000000-62115a9a95e60433c1f12016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxycoumestan 40V, Negative-QTOFsplash10-0f8i-0190000000-f278d30e8f42c660f3732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxycoumestan 10V, Positive-QTOFsplash10-0002-0090000000-0e40d1dc69d66b6011272021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxycoumestan 20V, Positive-QTOFsplash10-0002-0090000000-0e40d1dc69d66b6011272021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxycoumestan 40V, Positive-QTOFsplash10-0lka-0090000000-41180fc85ac6f531ed3f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxycoumestan 10V, Negative-QTOFsplash10-0002-0090000000-96de5c56a94c496da9f82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxycoumestan 20V, Negative-QTOFsplash10-0002-0090000000-64b3e7038d45fb334d982021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3,8-Dihydroxy-9-methoxycoumestan 40V, Negative-QTOFsplash10-0udi-0090000000-e1d47c3efc6a6c751de42021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDFDB002446
KNApSAcK IDC00009763
Chemspider ID24843112
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound44151023
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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
3,8-Dihydroxy-9-methoxycoumestan → 3,4,5-trihydroxy-6-({14-hydroxy-13-methoxy-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)oxane-2-carboxylic aciddetails
3,8-Dihydroxy-9-methoxycoumestan → 3,4,5-trihydroxy-6-({5-hydroxy-13-methoxy-9-oxo-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11,13,15-heptaen-14-yl}oxy)oxane-2-carboxylic aciddetails