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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:38:05 UTC
Update Date2022-03-07 02:53:53 UTC
HMDB IDHMDB0033861
Secondary Accession Numbers
  • HMDB33861
Metabolite Identification
Common Name3-Hydroxy-2,9-dimethoxypterocarpan
Description3-Hydroxy-2,9-dimethoxypterocarpan, also known as 2-methoxymedicarpin, belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Thus, 3-hydroxy-2,9-dimethoxypterocarpan is considered to be a flavonoid lipid molecule. 3-Hydroxy-2,9-dimethoxypterocarpan is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 3-hydroxy-2,9-dimethoxypterocarpan has been detected, but not quantified in, common pea and green vegetables. This could make 3-hydroxy-2,9-dimethoxypterocarpan a potential biomarker for the consumption of these foods.
Structure
Data?1563862472
Synonyms
ValueSource
2-MethoxymedicarpinHMDB
Chemical FormulaC17H16O5
Average Molecular Weight300.3059
Monoisotopic Molecular Weight300.099773622
IUPAC Name4,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaen-5-ol
Traditional Name4,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaen-5-ol
CAS Registry Number56752-00-2
SMILES
COC1=CC2=C(C=C1)C1COC3=CC(O)=C(OC)C=C3C1O2
InChI Identifier
InChI=1S/C17H16O5/c1-19-9-3-4-10-12-8-21-14-7-13(18)16(20-2)6-11(14)17(12)22-15(10)5-9/h3-7,12,17-18H,8H2,1-2H3
InChI KeyYVBGQNQUTOVRER-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassFuranoisoflavonoids
Direct ParentPterocarpans
Alternative Parents
Substituents
  • Pterocarpan
  • Isoflavanol
  • Isoflavan
  • Chromane
  • 1-benzopyran
  • Benzopyran
  • Coumaran
  • Benzofuran
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Benzenoid
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point146 - 148 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.082 g/LALOGPS
logP2.87ALOGPS
logP2.35ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.81ChemAxon
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area57.15 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity79.52 m³·mol⁻¹ChemAxon
Polarizability31.39 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]+171.51631661259
DarkChem[M-H]-172.52831661259
DeepCCS[M+H]+172.25130932474
DeepCCS[M-H]-169.89330932474
DeepCCS[M-2H]-203.53130932474
DeepCCS[M+Na]+178.75830932474
AllCCS[M+H]+170.432859911
AllCCS[M+H-H2O]+166.832859911
AllCCS[M+NH4]+173.832859911
AllCCS[M+Na]+174.732859911
AllCCS[M-H]-175.132859911
AllCCS[M+Na-2H]-174.432859911
AllCCS[M+HCOO]-173.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Hydroxy-2,9-dimethoxypterocarpanCOC1=CC2=C(C=C1)C1COC3=CC(O)=C(OC)C=C3C1O23789.6Standard polar33892256
3-Hydroxy-2,9-dimethoxypterocarpanCOC1=CC2=C(C=C1)C1COC3=CC(O)=C(OC)C=C3C1O22515.5Standard non polar33892256
3-Hydroxy-2,9-dimethoxypterocarpanCOC1=CC2=C(C=C1)C1COC3=CC(O)=C(OC)C=C3C1O22696.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Hydroxy-2,9-dimethoxypterocarpan,1TMS,isomer #1COC1=CC=C2C(=C1)OC1C3=CC(OC)=C(O[Si](C)(C)C)C=C3OCC212719.2Semi standard non polar33892256
3-Hydroxy-2,9-dimethoxypterocarpan,1TBDMS,isomer #1COC1=CC=C2C(=C1)OC1C3=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C=C3OCC212968.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-2,9-dimethoxypterocarpan GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-0790000000-e4d124ee53bb597490e02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-2,9-dimethoxypterocarpan GC-MS (1 TMS) - 70eV, Positivesplash10-0adj-2229000000-3d587c01c1d79f882e562017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-2,9-dimethoxypterocarpan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Hydroxy-2,9-dimethoxypterocarpan 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-Hydroxy-2,9-dimethoxypterocarpan 10V, Positive-QTOFsplash10-0udi-0019000000-4e4d6fc85631f493c06d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2,9-dimethoxypterocarpan 20V, Positive-QTOFsplash10-0udi-0169000000-3549759ff5fd1bd01f812015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2,9-dimethoxypterocarpan 40V, Positive-QTOFsplash10-0pb9-6970000000-700ccc8da5ff237812922015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2,9-dimethoxypterocarpan 10V, Negative-QTOFsplash10-0002-0090000000-081951735fb3a1c362972015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2,9-dimethoxypterocarpan 20V, Negative-QTOFsplash10-0002-0090000000-62cc26991aed0e2869c92015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2,9-dimethoxypterocarpan 40V, Negative-QTOFsplash10-0zi3-1190000000-55dd844fdf4979397b782015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2,9-dimethoxypterocarpan 10V, Positive-QTOFsplash10-0udi-0009000000-7fd5921050e52686aed72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2,9-dimethoxypterocarpan 20V, Positive-QTOFsplash10-0udi-0309000000-4eb183e887a1c812e3c12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2,9-dimethoxypterocarpan 40V, Positive-QTOFsplash10-0nvj-0940000000-94b15ec3ffed057320312021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2,9-dimethoxypterocarpan 10V, Negative-QTOFsplash10-0002-0090000000-c8e04b941de97dd002f42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2,9-dimethoxypterocarpan 20V, Negative-QTOFsplash10-0002-0090000000-15e14b14bf7d9096f8ab2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Hydroxy-2,9-dimethoxypterocarpan 40V, Negative-QTOFsplash10-0gir-0290000000-4bf75dad5d5351a95e0c2021-09-24Wishart 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 IDFDB012045
KNApSAcK IDC00009618
Chemspider ID24843008
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound12218868
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.. .