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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:45:42 UTC
Update Date2022-03-07 02:53:56 UTC
HMDB IDHMDB0033986
Secondary Accession Numbers
  • HMDB33986
Metabolite Identification
Common NameDemethylvestitol
DescriptionDemethylvestitol, also known as pipecurium or arduan, belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton. Thus, demethylvestitol is considered to be a flavonoid. Demethylvestitol has been detected, but not quantified in, several different foods, such as common beans (Phaseolus vulgaris), green beans (Phaseolus vulgaris), pulses, scarlet beans (Phaseolus coccineus), and yellow wax beans (Phaseolus vulgaris). This could make demethylvestitol a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Demethylvestitol.
Structure
Data?1563862491
Synonyms
ValueSource
PipecuroniumMeSH
Pipecuronium dibromide, (17 alpha)-isomerMeSH
Pipecuronium dibromide, (3 beta)-isomerMeSH
Pipecuronium dibromide, dihydrateMeSH
PipecuriumMeSH
Bromide, pipecuriumMeSH
Bromide, pipecuroniumMeSH
Pipecuronium bromideMeSH
Pipecuronium dibromide, (16 alpha)-isomerMeSH
ArduanMeSH
Dibromide pipecuroniumMeSH
Dibromide, dihydrate pipecuroniumMeSH
Dihydrate pipecuronium dibromideMeSH
Pipecurium bromideMeSH
Pipecuronium, dibromideMeSH
3,4-dihydro-3-(2,4-Dihydroxyphenyl)-7-hydroxy-2H-1-benzopyranHMDB
4-(3,4-dihydro-7-Hydroxy-2H-1-benzopyran-4-yl)-1,3-benzenediol, 9ciHMDB
7,2',4'-TrihydroxyisoflavanHMDB
pipecuronio BromuroHMDB
Chemical FormulaC15H14O4
Average Molecular Weight258.2693
Monoisotopic Molecular Weight258.089208936
IUPAC Name4-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)benzene-1,3-diol
Traditional Namedemethylvestitol
CAS Registry Number65332-45-8
SMILES
OC1=CC(O)=C(C=C1)C1COC2=C(C1)C=CC(O)=C2
InChI Identifier
InChI=1S/C15H14O4/c16-11-3-4-13(14(18)6-11)10-5-9-1-2-12(17)7-15(9)19-8-10/h1-4,6-7,10,16-18H,5,8H2
InChI KeyCJZBXHPHEBCWLV-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflavans
Direct ParentIsoflavanols
Alternative Parents
Substituents
  • Isoflavanol
  • Hydroxyisoflavonoid
  • Chromane
  • Benzopyran
  • 1-benzopyran
  • Resorcinol
  • Alkyl aryl ether
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Benzenoid
  • Monocyclic benzene moiety
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.088 g/LALOGPS
logP2.16ALOGPS
logP2.89ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)9.33ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area69.92 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity70.94 m³·mol⁻¹ChemAxon
Polarizability27.16 ųChemAxon
Number of Rings3ChemAxon
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]+160.8731661259
DarkChem[M-H]-157.90731661259
DeepCCS[M+H]+162.72330932474
DeepCCS[M-H]-160.36530932474
DeepCCS[M-2H]-193.25130932474
DeepCCS[M+Na]+168.81630932474
AllCCS[M+H]+159.932859911
AllCCS[M+H-H2O]+156.032859911
AllCCS[M+NH4]+163.632859911
AllCCS[M+Na]+164.632859911
AllCCS[M-H]-162.432859911
AllCCS[M+Na-2H]-161.832859911
AllCCS[M+HCOO]-161.332859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DemethylvestitolOC1=CC(O)=C(C=C1)C1COC2=C(C1)C=CC(O)=C23515.6Standard polar33892256
DemethylvestitolOC1=CC(O)=C(C=C1)C1COC2=C(C1)C=CC(O)=C22691.4Standard non polar33892256
DemethylvestitolOC1=CC(O)=C(C=C1)C1COC2=C(C1)C=CC(O)=C22869.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Demethylvestitol,1TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC=C3C2)C(O)=C12675.7Semi standard non polar33892256
Demethylvestitol,1TMS,isomer #2C[Si](C)(C)OC1=CC(O)=CC=C1C1COC2=CC(O)=CC=C2C12650.8Semi standard non polar33892256
Demethylvestitol,1TMS,isomer #3C[Si](C)(C)OC1=CC=C2CC(C3=CC=C(O)C=C3O)COC2=C12669.9Semi standard non polar33892256
Demethylvestitol,2TMS,isomer #1C[Si](C)(C)OC1=CC=C(C2COC3=CC(O[Si](C)(C)C)=CC=C3C2)C(O)=C12660.5Semi standard non polar33892256
Demethylvestitol,2TMS,isomer #2C[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC=C3C2)C(O[Si](C)(C)C)=C12696.9Semi standard non polar33892256
Demethylvestitol,2TMS,isomer #3C[Si](C)(C)OC1=CC=C2CC(C3=CC=C(O)C=C3O[Si](C)(C)C)COC2=C12684.4Semi standard non polar33892256
Demethylvestitol,3TMS,isomer #1C[Si](C)(C)OC1=CC=C2CC(C3=CC=C(O[Si](C)(C)C)C=C3O[Si](C)(C)C)COC2=C12617.3Semi standard non polar33892256
Demethylvestitol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC=C3C2)C(O)=C12956.5Semi standard non polar33892256
Demethylvestitol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC(O)=CC=C1C1COC2=CC(O)=CC=C2C12945.5Semi standard non polar33892256
Demethylvestitol,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2CC(C3=CC=C(O)C=C3O)COC2=C12960.3Semi standard non polar33892256
Demethylvestitol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C(C2COC3=CC(O[Si](C)(C)C(C)(C)C)=CC=C3C2)C(O)=C13187.3Semi standard non polar33892256
Demethylvestitol,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC1=CC=C(C2COC3=CC(O)=CC=C3C2)C(O[Si](C)(C)C(C)(C)C)=C13191.3Semi standard non polar33892256
Demethylvestitol,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC1=CC=C2CC(C3=CC=C(O)C=C3O[Si](C)(C)C(C)(C)C)COC2=C13188.2Semi standard non polar33892256
Demethylvestitol,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CC=C2CC(C3=CC=C(O[Si](C)(C)C(C)(C)C)C=C3O[Si](C)(C)C(C)(C)C)COC2=C13261.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Demethylvestitol GC-MS (Non-derivatized) - 70eV, Positivesplash10-0553-0590000000-2c0bca31092dfea212e72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Demethylvestitol GC-MS (3 TMS) - 70eV, Positivesplash10-0zmi-3022900000-4539bb07bfffda37b1742017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Demethylvestitol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Demethylvestitol 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 - Demethylvestitol 10V, Positive-QTOFsplash10-0ab9-0890000000-feebc814b570d18229732015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylvestitol 20V, Positive-QTOFsplash10-00dl-0950000000-8613c9fd6e87aaa46cfc2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylvestitol 40V, Positive-QTOFsplash10-05fr-3920000000-28cde73d029166d046272015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylvestitol 10V, Negative-QTOFsplash10-0a4i-0390000000-bc72e3f53044527a27552015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylvestitol 20V, Negative-QTOFsplash10-0a4i-0980000000-5c07eb85c5df3850f1822015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylvestitol 40V, Negative-QTOFsplash10-0ab9-3910000000-cdd6f51494588e40ce3b2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylvestitol 10V, Positive-QTOFsplash10-0a4j-0590000000-0fc888d544d19b178a042021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylvestitol 20V, Positive-QTOFsplash10-0a4j-0980000000-ff6cd3ec3ced984c021f2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylvestitol 40V, Positive-QTOFsplash10-00ri-4920000000-88560d7baa6e7c78b3302021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylvestitol 10V, Negative-QTOFsplash10-0a4i-0290000000-31d1297674ece6f611b52021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylvestitol 20V, Negative-QTOFsplash10-0a4i-0690000000-88623afb300c6aaee8222021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Demethylvestitol 40V, Negative-QTOFsplash10-01wr-0910000000-e1ac3be06a5cc42b713f2021-09-25Wishart LabView Spectrum
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
FooDB IDFDB012218
KNApSAcK IDC00009708
Chemspider ID509323
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound585939
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
Demethylvestitol → 6-{[3-(2,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
Demethylvestitol → 3,4,5-trihydroxy-6-[5-hydroxy-2-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)phenoxy]oxane-2-carboxylic aciddetails
Demethylvestitol → 3,4,5-trihydroxy-6-[3-hydroxy-4-(7-hydroxy-3,4-dihydro-2H-1-benzopyran-3-yl)phenoxy]oxane-2-carboxylic aciddetails