Identification

Name
Daidzin
Accession Number
DB02115  (EXPT01311)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • 7-(beta-D-glucopyranosyloxy)-3-(4-hydroxyphenyl)-4H-chromen-4-one
  • Daidzein 7-glucoside
  • daidzein 7-O-beta-D-glucoside
  • Daidzein 7-O-glucoside
  • daidzein 7-O-β-D-glucoside
  • Daidzoside
Categories
UNII
4R2X91A5M5
CAS number
552-66-9
Weight
Average: 416.3781
Monoisotopic: 416.110732238
Chemical Formula
C21H20O9
InChI Key
KYQZWONCHDNPDP-QNDFHXLGSA-N
InChI
InChI=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
IUPAC Name
3-(4-hydroxyphenyl)-7-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4H-chromen-4-one
SMILES
[H][[email protected]]1(CO)O[[email protected]@]([H])(OC2=CC=C3C(=O)C(=COC3=C2)C2=CC=C(O)C=C2)[[email protected]]([H])(O)[[email protected]@]([H])(O)[[email protected]]1([H])O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UAldehyde dehydrogenase, mitochondrialNot AvailableHuman
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Daidzin.Approved
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Daidzin.Approved, Investigational
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB33991
KEGG Compound
C10216
PubChem Compound
107971
PubChem Substance
46505206
ChemSpider
97088
BindingDB
50409029
ChEBI
42202
ChEMBL
CHEMBL486422
HET
DZN
PDB Entries
2vle

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.661 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity101.85 m3·mol-1ChemAxon
Polarizability41.25 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.7855
Blood Brain Barrier-0.6975
Caco-2 permeable-0.9398
P-glycoprotein substrateSubstrate0.5905
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.7968
Renal organic cation transporterNon-inhibitor0.8921
CYP450 2C9 substrateNon-substrate0.8116
CYP450 2D6 substrateNon-substrate0.8923
CYP450 3A4 substrateNon-substrate0.6035
CYP450 1A2 substrateNon-inhibitor0.9084
CYP450 2C9 inhibitorNon-inhibitor0.9296
CYP450 2D6 inhibitorNon-inhibitor0.9513
CYP450 2C19 inhibitorNon-inhibitor0.9289
CYP450 3A4 inhibitorNon-inhibitor0.9193
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7728
Ames testAMES toxic0.5776
CarcinogenicityNon-carcinogens0.9589
BiodegradationNot ready biodegradable0.6259
Rat acute toxicity2.3869 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9813
hERG inhibition (predictor II)Non-inhibitor0.6865
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 30V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 50V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 10V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 40V, NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0uxr-0190300000-7c009a9b8fd016988c20
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0090300000-87d938e172f23b8f9266
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0090101010-00cce9f1d03944bfc839
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0090000000-f372e3204e88dfa0fac6
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0089-2970000000-19bb9d5854402bda7386
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-0udi-0190200000-21f48ac2697d0d52ecd2
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udi-0090000000-65cde820e99b7330181c
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udi-0090000000-02d2e6531c1f5306a982
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udi-0090005000-e1a64aa9987c014a3479
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-0udi-0090005100-ebd792ec79716bac22ca
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0190000000-eda4bb0289e93579fe55
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0030900000-7d29657b93ed6a4bbec3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0090000000-73a8d0f2baf05f40f6e9
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-0290000000-0795fc21c6cff9c0c467
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a4i-0090000000-a25f56a591c58afb1c61
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0a4i-0090000000-527c23f9cfbe3a86c7e2
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004i-0090000000-c425a8b46f2dc4d72536
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004i-0090000000-ae032bd8003ed86f20b6
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-0090000000-d12ec587a61147da830d
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-0090000000-273e335a372f5ac1ea23
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-0006-0090000000-903bd33f9af9c7016ed7
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0000900000-797e615bdf73658b5954
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0000900000-df31914aab14f8c9945d
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0000900000-b0947fdf3f8f55af1663

Taxonomy

Description
This compound 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.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Isoflavonoids
Sub Class
Isoflavonoid O-glycosides
Direct Parent
Isoflavonoid O-glycosides
Alternative Parents
Isoflavones / Phenolic glycosides / Hexoses / Chromones / O-glycosyl compounds / Pyranones and derivatives / 1-hydroxy-2-unsubstituted benzenoids / Oxanes / Benzene and substituted derivatives / Heteroaromatic compounds
show 7 more
Substituents
Isoflavonoid o-glycoside / Isoflavonoid-7-o-glycoside / Isoflavone / Phenolic glycoside / Hexose monosaccharide / Chromone / Glycosyl compound / O-glycosyl compound / Benzopyran / 1-benzopyran
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
beta-D-glucoside, monosaccharide derivative, hydroxyisoflavone, glycosyloxyisoflavone (CHEBI:42202) / isoflavones, Isoflavonoids (C10216)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Electron carrier activity
Specific Function
Not Available
Gene Name
ALDH2
Uniprot ID
P05091
Uniprot Name
Aldehyde dehydrogenase, mitochondrial
Molecular Weight
56380.93 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Perez M, Real R, Mendoza G, Merino G, Prieto JG, Alvarez AI: Milk secretion of nitrofurantoin, as a specific BCRP/ABCG2 substrate, in assaf sheep: modulation by isoflavones. J Vet Pharmacol Ther. 2009 Oct;32(5):498-502. doi: 10.1111/j.1365-2885.2008.01050.x. [PubMed:19754918]

Drug created on June 13, 2005 07:24 / Updated on November 09, 2017 03:09