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Showing Compound Biochanin A 7-glucoside (FDB012224)

Record Information
Version1.0
Creation date2010-04-08 22:10:03 UTC
Update date2019-11-26 03:06:25 UTC
Primary IDFDB012224
Secondary Accession Numbers
  • FDB030698
Chemical Information
FooDB NameBiochanin A 7-glucoside
DescriptionSissotrin 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. Sissotrin has been detected, but not quantified in, chickpeas (Cicer arietinum). This could make sissotrin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Sissotrin.
CAS Number5928-26-7
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility0.62 g/LALOGPS
logP0.71ALOGPS
logP0.95ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)8.48ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area155.14 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity108.31 m³·mol⁻¹ChemAxon
Polarizability44.31 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC22H22O10
IUPAC name5-hydroxy-3-(4-methoxyphenyl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
InChI IdentifierInChI=1S/C22H22O10/c1-29-11-4-2-10(3-5-11)13-9-30-15-7-12(6-14(24)17(15)18(13)25)31-22-21(28)20(27)19(26)16(8-23)32-22/h2-7,9,16,19-24,26-28H,8H2,1H3
InChI KeyLFEUICHQZGNOHD-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC=C(C=C1)C1=COC2=CC(OC3OC(CO)C(O)C(O)C3O)=CC(O)=C2C1=O
Average Molecular Weight446.4041
Monoisotopic Molecular Weight446.121296924
Classification
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
  • 4p-o-methylisoflavone
  • Isoflavone
  • Hydroxyisoflavonoid
  • Phenolic glycoside
  • Hexose monosaccharide
  • O-glycosyl compound
  • Glycosyl compound
  • Chromone
  • 1-benzopyran
  • Benzopyran
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Pyranone
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyran
  • Monocyclic benzene moiety
  • Oxane
  • Monosaccharide
  • Benzenoid
  • Heteroaromatic compound
  • Vinylogous acid
  • Secondary alcohol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Ether
  • Polyol
  • Organic oxygen compound
  • Alcohol
  • Primary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
  • an isoflavone-7-O-β-D-glucoside (CPD-4563 )
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSBiochanin A 7-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05dr-9304500000-c8067e4a244e8912c60eSpectrum
Predicted GC-MSBiochanin A 7-glucoside, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0002-3284149000-322367cf04163cf070efSpectrum
Predicted GC-MSBiochanin A 7-glucoside, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0090000000-be48342f42bd053890692017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-001i-0090000000-c58519e7d50fc1a2e8b72017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0090000000-8bff1c76f275a85bc0772017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-5460225beb67664c34ad2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0090000000-bd891ccf84be93e05ea02017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-000i-0190000000-9c6c41f1ef3f1aa1326a2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0159-0090000000-545c1265f580f522051c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0390000000-22e8f3945c9529e07aae2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-001i-0090000000-b1e19c8f80d3eff8b9c82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-014i-0290000000-6572ea1a9c6ea4a5594a2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-0159-0090000000-df121f50b26cbbfe27672021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-001i-0090000000-8e863ca079207271e5772021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-001i-0090000000-3978f1f03bb553294eb82021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-0190700000-f08aa7a0e23a8580dddd2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-bb98343295ce289bf1e92015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-1290000000-4c7f39d1ef43c017ee612015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000j-0190700000-f08aa7a0e23a8580dddd2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0090000000-bb98343295ce289bf1e92015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014r-1290000000-4c7f39d1ef43c017ee612015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-1150900000-0fc47932bc1c259465b12015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1191200000-03f96e6d4ac25371ca792015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2290000000-e62e9c910ca9235a3bdf2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000t-1150900000-0fc47932bc1c259465b12015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-1191200000-03f96e6d4ac25371ca792015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-2290000000-e62e9c910ca9235a3bdf2015-04-25View Spectrum
NMRNot Available
ChemSpider ID4513980
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID5358913
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33990
CRC / DFC (Dictionary of Food Compounds) IDHFG01-K:HFG04-N
EAFUS IDNot Available
Dr. Duke IDBIOCHANIN-A-7-O-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDC00010112
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.