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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-12 01:40:13 UTC
Update Date2022-03-07 02:56:28 UTC
HMDB IDHMDB0040129
Secondary Accession Numbers
  • HMDB40129
Metabolite Identification
Common Name5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside
Description5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one. 5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside has been detected, but not quantified in, pulses. This could make 5,7-dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside.
Structure
Thumb
SynonymsNot Available
Chemical FormulaC23H24O10
Average Molecular Weight460.4307
Monoisotopic Molecular Weight460.136946988
IUPAC Name5-hydroxy-6-methoxy-3-(2-methoxyphenyl)-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4H-chromen-4-one
Traditional Name5-hydroxy-6-methoxy-3-(2-methoxyphenyl)-7-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one
CAS Registry Number275816-77-8
SMILES
COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O)C(O)C3O)=C(OC)C(O)=C2C1=O
InChI Identifier
InChI=1S/C23H24O10/c1-10-17(24)20(27)21(28)23(32-10)33-15-8-14-16(19(26)22(15)30-3)18(25)12(9-31-14)11-6-4-5-7-13(11)29-2/h4-10,17,20-21,23-24,26-28H,1-3H3
InChI KeyWNIHYNZJOPCHOA-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as isoflavonoid o-glycosides. These are o-glycosylated derivatives of isoflavonoids, which are natural products derived from 3-phenylchromen-4-one.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassIsoflavonoids
Sub ClassIsoflavonoid O-glycosides
Direct ParentIsoflavonoid O-glycosides
Alternative Parents
Substituents
  • Isoflavonoid o-glycoside
  • Isoflavonoid-7-o-glycoside
  • Hydroxyisoflavonoid
  • Isoflavone
  • Phenolic glycoside
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Phenoxy compound
  • Methoxybenzene
  • Phenol ether
  • Pyranone
  • Alkyl aryl ether
  • 1-hydroxy-4-unsubstituted benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Organooxygen compound
  • Alcohol
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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 Solubility0.48 g/LALOGPS
logP1.58ALOGPS
logP1.84ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)9.05ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area144.14 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity113.23 m³·mol⁻¹ChemAxon
Polarizability46.02 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]+207.85531661259
DarkChem[M-H]-202.55131661259
DeepCCS[M+H]+196.95430932474
DeepCCS[M-H]-194.59630932474
DeepCCS[M-2H]-227.98830932474
DeepCCS[M+Na]+203.21630932474
AllCCS[M+H]+208.432859911
AllCCS[M+H-H2O]+206.132859911
AllCCS[M+NH4]+210.532859911
AllCCS[M+Na]+211.132859911
AllCCS[M-H]-206.332859911
AllCCS[M+Na-2H]-207.032859911
AllCCS[M+HCOO]-207.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnosideCOC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O)C(O)C3O)=C(OC)C(O)=C2C1=O4695.5Standard polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnosideCOC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O)C(O)C3O)=C(OC)C(O)=C2C1=O3736.7Standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnosideCOC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O)C(O)C3O)=C(OC)C(O)=C2C1=O4027.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,1TMS,isomer #1COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O[Si](C)(C)C)C(O)C3O)=C(OC)C(O)=C2C1=O3748.5Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,1TMS,isomer #2COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O)C(O[Si](C)(C)C)C3O)=C(OC)C(O)=C2C1=O3729.0Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,1TMS,isomer #3COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O)C(O)C3O[Si](C)(C)C)=C(OC)C(O)=C2C1=O3728.4Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,1TMS,isomer #4COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O)C(O)C3O)=C(OC)C(O[Si](C)(C)C)=C2C1=O3827.4Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,2TMS,isomer #1COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O)=C(OC)C(O)=C2C1=O3608.0Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,2TMS,isomer #2COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O[Si](C)(C)C)C(O)C3O[Si](C)(C)C)=C(OC)C(O)=C2C1=O3632.7Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,2TMS,isomer #3COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O[Si](C)(C)C)C(O)C3O)=C(OC)C(O[Si](C)(C)C)=C2C1=O3661.2Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,2TMS,isomer #4COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O)C(O[Si](C)(C)C)C3O[Si](C)(C)C)=C(OC)C(O)=C2C1=O3621.1Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,2TMS,isomer #5COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O)C(O[Si](C)(C)C)C3O)=C(OC)C(O[Si](C)(C)C)=C2C1=O3618.2Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,2TMS,isomer #6COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O)C(O)C3O[Si](C)(C)C)=C(OC)C(O[Si](C)(C)C)=C2C1=O3644.9Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,3TMS,isomer #1COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O[Si](C)(C)C)=C(OC)C(O)=C2C1=O3555.0Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,3TMS,isomer #2COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O)=C(OC)C(O[Si](C)(C)C)=C2C1=O3542.7Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,3TMS,isomer #3COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O[Si](C)(C)C)C(O)C3O[Si](C)(C)C)=C(OC)C(O[Si](C)(C)C)=C2C1=O3572.6Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,3TMS,isomer #4COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O)C(O[Si](C)(C)C)C3O[Si](C)(C)C)=C(OC)C(O[Si](C)(C)C)=C2C1=O3543.0Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,4TMS,isomer #1COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C3O[Si](C)(C)C)=C(OC)C(O[Si](C)(C)C)=C2C1=O3535.2Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,1TBDMS,isomer #1COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O[Si](C)(C)C(C)(C)C)C(O)C3O)=C(OC)C(O)=C2C1=O3991.1Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,1TBDMS,isomer #2COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O)C(O[Si](C)(C)C(C)(C)C)C3O)=C(OC)C(O)=C2C1=O3962.8Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,1TBDMS,isomer #3COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O)C(O)C3O[Si](C)(C)C(C)(C)C)=C(OC)C(O)=C2C1=O3980.0Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,1TBDMS,isomer #4COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O)C(O)C3O)=C(OC)C(O[Si](C)(C)C(C)(C)C)=C2C1=O4038.2Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,2TBDMS,isomer #1COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O)=C(OC)C(O)=C2C1=O4040.6Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,2TBDMS,isomer #2COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O[Si](C)(C)C(C)(C)C)C(O)C3O[Si](C)(C)C(C)(C)C)=C(OC)C(O)=C2C1=O4066.8Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,2TBDMS,isomer #3COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O[Si](C)(C)C(C)(C)C)C(O)C3O)=C(OC)C(O[Si](C)(C)C(C)(C)C)=C2C1=O4071.2Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,2TBDMS,isomer #4COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)=C(OC)C(O)=C2C1=O4059.7Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,2TBDMS,isomer #5COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O)C(O[Si](C)(C)C(C)(C)C)C3O)=C(OC)C(O[Si](C)(C)C(C)(C)C)=C2C1=O4040.5Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,2TBDMS,isomer #6COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O)C(O)C3O[Si](C)(C)C(C)(C)C)=C(OC)C(O[Si](C)(C)C(C)(C)C)=C2C1=O4044.8Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,3TBDMS,isomer #1COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)=C(OC)C(O)=C2C1=O4152.5Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,3TBDMS,isomer #2COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C3O)=C(OC)C(O[Si](C)(C)C(C)(C)C)=C2C1=O4140.7Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,3TBDMS,isomer #3COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O[Si](C)(C)C(C)(C)C)C(O)C3O[Si](C)(C)C(C)(C)C)=C(OC)C(O[Si](C)(C)C(C)(C)C)=C2C1=O4145.2Semi standard non polar33892256
5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside,3TBDMS,isomer #4COC1=CC=CC=C1C1=COC2=CC(OC3OC(C)C(O)C(O[Si](C)(C)C(C)(C)C)C3O[Si](C)(C)C(C)(C)C)=C(OC)C(O[Si](C)(C)C(C)(C)C)=C2C1=O4141.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9103400000-1ec0b948641945f4ea802017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside GC-MS (3 TMS) - 70eV, Positivesplash10-03di-3113019000-aa1c58635e3d84a400352017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside 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 - 5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside 10V, Positive-QTOFsplash10-02ta-0168900000-1f9ba83061a05128b1902017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside 20V, Positive-QTOFsplash10-014j-0498000000-d5dfffc18124d2478ee02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside 40V, Positive-QTOFsplash10-05mk-1291000000-dd22961c1913ea77138c2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside 10V, Negative-QTOFsplash10-0bt9-2106900000-76f1875d6ab4c07f1bd32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside 20V, Negative-QTOFsplash10-08fs-1369400000-d33d05aef9d6da296e4a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside 40V, Negative-QTOFsplash10-0bt9-6894000000-5624d04076f3b9fdfe0a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside 10V, Positive-QTOFsplash10-014i-0009200000-c569657e6106fb60d1dc2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside 20V, Positive-QTOFsplash10-014i-0069000000-77992a929ac8441b7ab32021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside 40V, Positive-QTOFsplash10-03dm-5249100000-e3f1dd03926fc148c82d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside 10V, Negative-QTOFsplash10-0a4i-0001900000-759920f3de5d633f44512021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside 20V, Negative-QTOFsplash10-03di-1279600000-3046fee7adcce24575722021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 5,7-Dihydroxy-2',6-dimethoxyisoflavone 7-rhamnoside 40V, Negative-QTOFsplash10-07c7-1091100000-6109501b9d89b492080e2021-09-25Wishart 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 IDFDB019822
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131752779
PDB IDNot Available
ChEBI ID168269
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.. .