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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:35:27 UTC
Update Date2022-03-07 02:53:52 UTC
HMDB IDHMDB0033817
Secondary Accession Numbers
  • HMDB33817
Metabolite Identification
Common Name4-Hydroxy-2,3,9-trimethoxypterocarpan
Description4-Hydroxy-2,3,9-trimethoxypterocarpan 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, 4-hydroxy-2,3,9-trimethoxypterocarpan is considered to be a flavonoid. 4-Hydroxy-2,3,9-trimethoxypterocarpan has been detected, but not quantified in, common peas (Pisum sativum) and pulses. This could make 4-hydroxy-2,3,9-trimethoxypterocarpan a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 4-Hydroxy-2,3,9-trimethoxypterocarpan.
Structure
Data?1563862465
Synonyms
ValueSource
6a,11a-dihydro-2,3,9-Trimethoxy-6H-benzofuro[3,2-c][1]benzopyran-4-ol, 9ciHMDB
Chemical FormulaC18H18O6
Average Molecular Weight330.3319
Monoisotopic Molecular Weight330.110338308
IUPAC Name4,5,14-trimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaen-6-ol
Traditional Name4,5,14-trimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2,4,6,11(16),12,14-hexaen-6-ol
CAS Registry Number56841-82-8
SMILES
COC1=CC2=C(C=C1)C1COC3=C(O)C(OC)=C(OC)C=C3C1O2
InChI Identifier
InChI=1S/C18H18O6/c1-20-9-4-5-10-12-8-23-17-11(16(12)24-13(10)6-9)7-14(21-2)18(22-3)15(17)19/h4-7,12,16,19H,8H2,1-3H3
InChI KeyAPDOGYRSSCEXNB-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-4-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 Point141 - 145 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.099 g/LALOGPS
logP2.61ALOGPS
logP2.19ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)9.17ChemAxon
pKa (Strongest Basic)-4.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.38 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity85.99 m³·mol⁻¹ChemAxon
Polarizability34.33 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]+178.24631661259
DarkChem[M-H]-178.1331661259
DeepCCS[M+H]+177.74930932474
DeepCCS[M-H]-175.39130932474
DeepCCS[M-2H]-209.46330932474
DeepCCS[M+Na]+184.6930932474
AllCCS[M+H]+177.832859911
AllCCS[M+H-H2O]+174.532859911
AllCCS[M+NH4]+180.932859911
AllCCS[M+Na]+181.832859911
AllCCS[M-H]-182.432859911
AllCCS[M+Na-2H]-182.032859911
AllCCS[M+HCOO]-181.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-Hydroxy-2,3,9-trimethoxypterocarpanCOC1=CC2=C(C=C1)C1COC3=C(O)C(OC)=C(OC)C=C3C1O24068.5Standard polar33892256
4-Hydroxy-2,3,9-trimethoxypterocarpanCOC1=CC2=C(C=C1)C1COC3=C(O)C(OC)=C(OC)C=C3C1O22670.3Standard non polar33892256
4-Hydroxy-2,3,9-trimethoxypterocarpanCOC1=CC2=C(C=C1)C1COC3=C(O)C(OC)=C(OC)C=C3C1O22827.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Hydroxy-2,3,9-trimethoxypterocarpan,1TMS,isomer #1COC1=CC=C2C(=C1)OC1C3=CC(OC)=C(OC)C(O[Si](C)(C)C)=C3OCC212822.6Semi standard non polar33892256
4-Hydroxy-2,3,9-trimethoxypterocarpan,1TBDMS,isomer #1COC1=CC=C2C(=C1)OC1C3=CC(OC)=C(OC)C(O[Si](C)(C)C(C)(C)C)=C3OCC213058.1Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gba-0739000000-1612946b221d02cc00482017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan GC-MS (1 TMS) - 70eV, Positivesplash10-0079-1129000000-50a1ad62992542def8ab2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 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 - 4-Hydroxy-2,3,9-trimethoxypterocarpan 10V, Positive-QTOFsplash10-00lr-0509000000-1fb33ec9c409a691f00a2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 20V, Positive-QTOFsplash10-00lr-0629000000-0ff70174fb6e16fab96c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 40V, Positive-QTOFsplash10-03y1-2910000000-f098e6385ff8e7a725702016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 10V, Negative-QTOFsplash10-004i-0009000000-38d5cd86001d90f602bf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 20V, Negative-QTOFsplash10-01ta-0069000000-9f5a67b20b156424917c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 40V, Negative-QTOFsplash10-06wc-2390000000-dfbed0c21ebeb62a90622016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 10V, Positive-QTOFsplash10-001i-0009000000-2160799bc7c624fd06462021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 20V, Positive-QTOFsplash10-001i-0009000000-b00061307acdcb1e67c02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 40V, Positive-QTOFsplash10-03xr-0693000000-208fd85a933bc5628f9d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 10V, Negative-QTOFsplash10-004i-0009000000-de11969ae6615b28f3d72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 20V, Negative-QTOFsplash10-016s-0094000000-4d8d06564b41844767d62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Hydroxy-2,3,9-trimethoxypterocarpan 40V, Negative-QTOFsplash10-05mx-2191000000-b9eda0f9598c4758bd082021-09-24Wishart 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 IDFDB011981
KNApSAcK IDC00009633
Chemspider ID24843022
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound23036629
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.. .