Daidzin (CHEM028101)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:13:17 UTC
Update Date2016-11-09 01:18:36 UTC
Accession NumberCHEM028101
Identification
Common NameDaidzin
ClassSmall Molecule
DescriptionA glycosyloxyisoflavone that is daidzein attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It is used in the treatment of alcohol dependency (antidipsotropic).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
Daidzein 7-glucosideChEBI
Daidzein 7-O-glucosideChEBI
DaidzosideChEBI
7-O-Glucosyl-4'-hydroxyisoflavoneMeSH
4',7-Dihydroxyisoflavone 7-O-b-D-glucopyranosideHMDB
Daidzein 7-O-beta-D-glucopyranosideHMDB
Daidzein 7-O-beta-D-glucosideHMDB
DZNHMDB
DaidzinChEBI
Daidzein 7-O-b-D-glucosideGenerator, HMDB
Daidzein 7-O-β-D-glucosideGenerator, HMDB
Chemical FormulaC21H20O9
Average Molecular Mass416.382 g/mol
Monoisotopic Mass416.111 g/mol
CAS Registry Number552-66-9
IUPAC Name3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
Traditional Namedaidzin
SMILESOC[C@H]1O[C@@H](OC2=CC3=C(C=C2)C(=O)C(=CO3)C2=CC=C(O)C=C2)[C@H](O)[C@@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C21H20O9/c22-8-16-18(25)19(26)20(27)21(30-16)29-12-5-6-13-15(7-12)28-9-14(17(13)24)10-1-3-11(23)4-2-10/h1-7,9,16,18-23,25-27H,8H2/t16-,18-,19+,20-,21-/m1/s1
InChI KeyKYQZWONCHDNPDP-QNDFHXLGSA-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
  • Isoflavone
  • Phenolic glycoside
  • Hexose monosaccharide
  • Chromone
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Pyran
  • Monocyclic benzene moiety
  • Oxane
  • Benzenoid
  • Monosaccharide
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • Acetal
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxide
  • Organic oxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.66 g/LALOGPS
logP0.71ALOGPS
logP0.46ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)8.96ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.91 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity101.85 m³·mol⁻¹ChemAxon
Polarizability41.25 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f72-5619000000-9a00dd3afb417b948c0dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-014i-3614129000-e673b080216b7c841658Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-03di-0000092000-84a513c4afef1602030fSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-03di-0000092000-84a513c4afef1602030fSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-03di-0000900000-a8a90b48831795fcef5bSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-03di-0000900000-a8a90b48831795fcef5bSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0w29-0090800000-71336b3ac56112e89965Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0w29-0090800000-71336b3ac56112e89965Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0udi-0090100000-a3ff46535f112a06438eSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 50V, Negativesplash10-0udi-0090000000-806672a9fe6ab0e8821bSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-03di-0000900000-a8a90b48831795fcef5bSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0udi-0090300000-0e1086947a1b1fb0fc9cSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0w29-0090800000-71336b3ac56112e89965Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0udi-0090000000-3c95cabcacf790fe32beSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0uxr-0190300000-7c009a9b8fd016988c20Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0090300000-87d938e172f23b8f9266Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0090101010-00cce9f1d03944bfc839Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0090000000-f372e3204e88dfa0fac6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0089-2970000000-19bb9d5854402bda7386Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0190200000-21f48ac2697d0d52ecd2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0udi-0090000000-65cde820e99b7330181cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0aor-0194400000-29efa8833365732bd0d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0090000000-c52f4b92c3ebc772069dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-2290000000-8c00534d044e8a4e8e17Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0gb9-1173900000-06545d43f6fa1210591aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-1091000000-d49a71a5c4f62e485da7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-3390000000-2d121e77ef35344d0179Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB02115
HMDB IDHMDB0033991
FooDB IDFDB012225
Phenol Explorer ID403
KNApSAcK IDC00002518
BiGG IDNot Available
BioCyc IDCPD-3424
METLIN IDNot Available
PDB IDDZN
Wikipedia LinkDaidzin
Chemspider ID97088
ChEBI ID42202
PubChem Compound ID107971
Kegg Compound IDC10216
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=18613661
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=24154619
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=24483603
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=25209298
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=25236207
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=25746576
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=25845411
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=8433985
9. Kato K, Takahashi S, Cui L, Toda T, Suzuki S, Futakuchi M, Sugiura S, Shirai T: Suppressive effects of dietary genistin and daidzin on rat prostate carcinogenesis. Jpn J Cancer Res. 2000 Aug;91(8):786-91.
10. Choo MK, Park EK, Yoon HK, Kim DH: Antithrombotic and antiallergic activities of daidzein, a metabolite of puerarin and daidzin produced by human intestinal microflora. Biol Pharm Bull. 2002 Oct;25(10):1328-32.
11. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.