Record Information
Version1.0
Creation date2010-04-08 22:05:27 UTC
Update date2020-02-24 19:10:34 UTC
Primary IDFDB002609
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name6''-Acetyldaidzin
Description6''-O-Acetyldaidzin, also known as daidzein 6''-O-acetate, 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''-O-Acetyldaidzin is an extremely weak basic (essentially neutral) compound (based on its pKa). 6''-O-Acetyldaidzin is found, on average, in the highest concentration within a few different foods, such as soy beans, soy yogurts, and other soy products and in a lower concentration in miso, soy milks, and tofus. 6''-O-Acetyldaidzin has also been detected, but not quantified in, pulses and soy sauces. This could make 6''-O-acetyldaidzin a potential biomarker for the consumption of these foods.
CAS Number71385-83-6
Structure
Thumb
Synonyms
SynonymSource
6"-O-acetyldaidzinHMDB
6-O-AcetyldaidzinHMDB
Daidzein 6''-O-acetateHMDB
(3,4,5-Trihydroxy-6-{[3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methyl acetic acidGenerator
6''-Acetyldaidzein 7-glucosidemanual
6''-Acetyldaidzinmanual
6''-O-Acetyldaidzein 7-O-glucosidemanual
6''-O-Acetyldaidzindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.35 g/LALOGPS
logP1.43ALOGPS
logP0.9ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)8.96ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area151.98 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity111 m³·mol⁻¹ChemAxon
Polarizability45.38 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC23H22O10
IUPAC name(3,4,5-trihydroxy-6-{[3-(4-hydroxyphenyl)-4-oxo-4H-chromen-7-yl]oxy}oxan-2-yl)methyl acetate
InChI IdentifierInChI=1S/C23H22O10/c1-11(24)30-10-18-20(27)21(28)22(29)23(33-18)32-14-6-7-15-17(8-14)31-9-16(19(15)26)12-2-4-13(25)5-3-12/h2-9,18,20-23,25,27-29H,10H2,1H3
InChI KeyZMOZJTDOTOZVRT-UHFFFAOYSA-N
Isomeric SMILESCC(=O)OCC1OC(OC2=CC3=C(C=C2)C(=O)C(=CO3)C2=CC=C(O)C=C2)C(O)C(O)C1O
Average Molecular Weight458.419
Monoisotopic Molecular Weight458.121296908
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
  • Phenolic glycoside
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Monocyclic benzene moiety
  • Monosaccharide
  • Benzenoid
  • Oxane
  • Pyran
  • Heteroaromatic compound
  • Carboxylic acid ester
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Oxacycle
  • Carboxylic acid derivative
  • Acetal
  • Polyol
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organooxygen compound
  • Organic oxygen compound
  • 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 60.26%; H 4.84%; O 34.90%DFC
Melting PointMp 186-189°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
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4l-9334500000-380823433d6fc23ef636JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-0r03-4133009000-3493ed7aaa29f3bdccebJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1092600000-3b19d6e84cb3fd3d3392JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-6227eb87833c05a4d5baJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-3290000000-bbd3bced8babef48bd98JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9141600000-26f693d837da71111b00JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-9071000000-87ff915f3f672dd9f8a7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0zfr-8290000000-37355f579429bdeca897JSpectraViewer
ChemSpider ID26463584
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID53398699
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID401
DrugBank IDNot Available
HMDB IDHMDB30689
CRC / DFC (Dictionary of Food Compounds) IDCMR01-H:CMR06-M
EAFUS IDNot Available
Dr. Duke ID6"-O-ACETYL-DAIDZIN
BIGG IDNot Available
KNApSAcK IDC00010078
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.