Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:00:23 UTC
Update Date2022-03-07 02:53:39 UTC
HMDB IDHMDB0033292
Secondary Accession Numbers
  • HMDB33292
Metabolite Identification
Common Name8-Hydroxy-3,9-dimethoxypterocarpan
Description8-Hydroxy-3,9-dimethoxypterocarpan 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, 8-hydroxy-3,9-dimethoxypterocarpan is considered to be a flavonoid lipid molecule. 8-Hydroxy-3,9-dimethoxypterocarpan is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 8-hydroxy-3,9-dimethoxypterocarpan has been detected, but not quantified in, green vegetables. This could make 8-hydroxy-3,9-dimethoxypterocarpan a potential biomarker for the consumption of these foods.
Structure
Data?1563862382
Synonyms
ValueSource
(6AR,11ar)-8-hydroxy-3,9-dimethoxypterocarpanHMDB
Chemical FormulaC17H16O5
Average Molecular Weight300.3059
Monoisotopic Molecular Weight300.099773622
IUPAC Name5,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaen-13-ol
Traditional Name5,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaen-13-ol
CAS Registry Number108335-31-5
SMILES
COC1=CC2=C(C=C1)C1OC3=CC(OC)=C(O)C=C3C1CO2
InChI Identifier
InChI=1S/C17H16O5/c1-19-9-3-4-10-14(5-9)21-8-12-11-6-13(18)16(20-2)7-15(11)22-17(10)12/h3-7,12,17-18H,8H2,1-2H3
InChI KeyKIKDCPYSYOMXEJ-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 ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point129 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.089 g/LALOGPS
logP2.87ALOGPS
logP2.35ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)10.32ChemAxon
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
Polarizability31.31 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]+170.9731661259
DarkChem[M-H]-172.18831661259
DeepCCS[M+H]+175.32930932474
DeepCCS[M-H]-172.97230932474
DeepCCS[M-2H]-205.87730932474
DeepCCS[M+Na]+181.42330932474
AllCCS[M+H]+170.932859911
AllCCS[M+H-H2O]+167.332859911
AllCCS[M+NH4]+174.232859911
AllCCS[M+Na]+175.232859911
AllCCS[M-H]-175.332859911
AllCCS[M+Na-2H]-174.732859911
AllCCS[M+HCOO]-174.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
8-Hydroxy-3,9-dimethoxypterocarpanCOC1=CC2=C(C=C1)C1OC3=CC(OC)=C(O)C=C3C1CO23806.9Standard polar33892256
8-Hydroxy-3,9-dimethoxypterocarpanCOC1=CC2=C(C=C1)C1OC3=CC(OC)=C(O)C=C3C1CO22520.1Standard non polar33892256
8-Hydroxy-3,9-dimethoxypterocarpanCOC1=CC2=C(C=C1)C1OC3=CC(OC)=C(O)C=C3C1CO22709.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
8-Hydroxy-3,9-dimethoxypterocarpan,1TMS,isomer #1COC1=CC=C2C(=C1)OCC1C3=CC(O[Si](C)(C)C)=C(OC)C=C3OC212729.7Semi standard non polar33892256
8-Hydroxy-3,9-dimethoxypterocarpan,1TBDMS,isomer #1COC1=CC=C2C(=C1)OCC1C3=CC(O[Si](C)(C)C(C)(C)C)=C(OC)C=C3OC212988.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxy-3,9-dimethoxypterocarpan GC-MS (Non-derivatized) - 70eV, Positivesplash10-0229-0890000000-76dfcd08ccb9327275e22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxy-3,9-dimethoxypterocarpan GC-MS (1 TMS) - 70eV, Positivesplash10-0ab9-2329000000-35c2b549957cc48560152017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 8-Hydroxy-3,9-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 - 8-Hydroxy-3,9-dimethoxypterocarpan 10V, Positive-QTOFsplash10-0udi-0019000000-63da12e8b050a75505ca2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxy-3,9-dimethoxypterocarpan 20V, Positive-QTOFsplash10-0udi-0249000000-470f9309267f1265004f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxy-3,9-dimethoxypterocarpan 40V, Positive-QTOFsplash10-0pb9-6960000000-b7337bd9416a186852112015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxy-3,9-dimethoxypterocarpan 10V, Negative-QTOFsplash10-0002-0090000000-7f2d02992916d44d180d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxy-3,9-dimethoxypterocarpan 20V, Negative-QTOFsplash10-0002-0090000000-43aa7e31c85785ac928a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxy-3,9-dimethoxypterocarpan 40V, Negative-QTOFsplash10-0udr-1190000000-3c583683043c63d2b0682015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxy-3,9-dimethoxypterocarpan 10V, Negative-QTOFsplash10-0002-0090000000-c8e04b941de97dd002f42021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxy-3,9-dimethoxypterocarpan 20V, Negative-QTOFsplash10-0002-0090000000-b7824e819e86dc962cb62021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxy-3,9-dimethoxypterocarpan 40V, Negative-QTOFsplash10-0ldr-1290000000-571e00ca4365ce610ee92021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxy-3,9-dimethoxypterocarpan 10V, Positive-QTOFsplash10-0udi-0009000000-7fd5921050e52686aed72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxy-3,9-dimethoxypterocarpan 20V, Positive-QTOFsplash10-0udi-0219000000-9b6f093db77e957eefc72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 8-Hydroxy-3,9-dimethoxypterocarpan 40V, Positive-QTOFsplash10-070i-0950000000-468f33b7192f0baf752e2021-09-25Wishart 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 IDFDB011316
KNApSAcK IDC00010007
Chemspider ID400548
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound454891
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
8-Hydroxy-3,9-dimethoxypterocarpan → 6-({5,14-dimethoxy-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-2(7),3,5,11,13,15-hexaen-13-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic aciddetails