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Showing Compound 6''-Malonylgenistin (FDB000670)

Record Information
Version1.0
Creation date2010-04-08 22:04:40 UTC
Update date2020-02-24 19:10:11 UTC
Primary IDFDB000670
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name6''-Malonylgenistin
Description6''-Malonylgenistin 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. 6''-Malonylgenistin is found, on average, in the highest concentration within a few different foods, such as soy beans (Glycine max), yogurt, and soy yogurt and in a lower concentration in soy milk, miso, and other soy product. 6''-Malonylgenistin has also been detected, but not quantified in, soy sauce and white lupines (Lupinus albus). This could make 6''-malonylgenistin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 6''-Malonylgenistin.
CAS Number51011-05-3
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Genistein 7-O-glucoside 6''-malonateHMDB
Genistein 7-O-glucoside-6''-malonateHMDB
3-oxo-3-[(3,4,5-Trihydroxy-6-{[5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methoxy]propanoateGenerator
6''-Malonylgenistindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.6 g/LALOGPS
logP1.34ALOGPS
logP1.14ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)3.37ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area209.51 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity119.32 m³·mol⁻¹ChemAxon
Polarizability49.19 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC24H22O13
IUPAC name3-oxo-3-[(3,4,5-trihydroxy-6-{[5-hydroxy-3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methoxy]propanoic acid
InChI IdentifierInChI=1S/C24H22O13/c25-11-3-1-10(2-4-11)13-8-34-15-6-12(5-14(26)19(15)20(13)30)36-24-23(33)22(32)21(31)16(37-24)9-35-18(29)7-17(27)28/h1-6,8,16,21-26,31-33H,7,9H2,(H,27,28)
InChI KeyFRAUJUKWSKMNJY-UHFFFAOYSA-N
Isomeric SMILESOC1C(O)C(COC(=O)CC(O)=O)OC(OC2=CC3=C(C(O)=C2)C(=O)C(=CO3)C2=CC=C(O)C=C2)C1O
Average Molecular Weight518.427
Monoisotopic Molecular Weight518.106040768
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
  • Isoflavone
  • Hydroxyisoflavonoid
  • Phenolic glycoside
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Pyran
  • Monocyclic benzene moiety
  • Benzenoid
  • Oxane
  • 1,3-dicarbonyl compound
  • Monosaccharide
  • Dicarboxylic acid or derivatives
  • Vinylogous acid
  • Heteroaromatic compound
  • Secondary alcohol
  • Carboxylic acid ester
  • Polyol
  • Organoheterocyclic compound
  • Acetal
  • Carboxylic acid derivative
  • Oxacycle
  • Carboxylic acid
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 55.60%; H 4.28%; O 40.12%DFC
Melting PointMp 145°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MS6''-Malonylgenistin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0f79-9231420000-185872bba2b71d7467aaSpectrum
Predicted GC-MS6''-Malonylgenistin, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000b-9611136000-dc39481dfb81cf69ede7Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-0090020000-33b3c745963752e06bc92021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-0290020000-7d56ba8ce789064d20b32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 6V, Positivesplash10-00di-0090020000-af1c0fcfe6600962b6002021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00xr-3090560000-5d26a9734130b2b0bac52016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-1090100000-fab4ef8e871d5828db262016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-3290000000-422f7342cb8e1e10d44c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gc0-9861640000-dc579a176109b43a4f032016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0gb9-7590300000-05d28895ece855e344422016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-5490000000-77c80fef1bd5ed066cb72016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01b9-0070290000-778d9767990c94ee266b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0395700000-c3c19f6fd25f78fe666b2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9281310000-f7a14038cea98b0407df2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01b9-1050910000-f93e056208c10804b8b62021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-3090300000-f184136a7c0325b812bb2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9050000000-40c49d3826633293286c2021-09-22View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC16192
Pubchem Compound ID15934091
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID402
DrugBank IDNot Available
HMDB IDHMDB29529
CRC / DFC (Dictionary of Food Compounds) IDGZR02-N:BFL73-S
EAFUS IDNot Available
Dr. Duke IDMALONYLGENISTIN|6"-O-MALONYLGENISTIN
BIGG IDNot Available
KNApSAcK IDC00010110
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— 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.