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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H20O9
Molecular Weight 416.3781
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DAIDZIN

SMILES

OC[C@H]1O[C@@H](OC2=CC=C3C(=O)C(=COC3=C2)C4=CC=C(O)C=C4)[C@H](O)[C@@H](O)[C@@H]1O

InChI

InChIKey=KYQZWONCHDNPDP-QNDFHXLGSA-N
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

HIDE SMILES / InChI

Molecular Formula C21H20O9
Molecular Weight 416.3781
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

The three major isoflavones present in kudzu extracts, daidzin, daidzein and puerarin are responsible for the beneficial effects in reduction of alcohol consumption. It has been discovered, that daidzin was a strong, selective and reversible inhibitor of mitochondrial aldehyde dehydrogenase. Daidzin did not inhibit human class I, II, or III alcohol dehydrogenases. However further studies for daidzin’s treatment in alcohol addiction were discontinued.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P05091
Gene ID: 217.0
Gene Symbol: ALDH2
Target Organism: Homo sapiens (Human)
80.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Suppressive effects of dietary genistin and daidzin on rat prostate carcinogenesis.
2000 Aug
Intestinal bacteria activate estrogenic effect of main constituents puerarin and daidzin of Pueraria thunbergiana.
2006 Dec
Absorption and metabolism of Astragali radix decoction: in silico, in vitro, and a case study in vivo.
2006 Jun
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Bioactive flavonoids of the flowers of Butea monosperma.
2009 Apr
Role of plasma lipoproteins in the transport of the soyabean isoflavones daidzein and daidzein-7-O-beta-D-glucoside.
2009 Sep
The effects of daidzin and its aglycon, daidzein, on the scopolamine-induced memory impairment in male mice.
2010 Oct
Discovery of novel regulators of aldehyde dehydrogenase isoenzymes.
2011 May 30
Methylmercury impairs canonical dopamine metabolism in rat undifferentiated pheochromocytoma (PC12) cells by indirect inhibition of aldehyde dehydrogenase.
2015 Apr
Patents

Sample Use Guides

in rats: orally administered at a dose of 7.9 micromol/kg in 25 mM Na2CO3
Route of Administration: Oral
In Vitro Use Guide
Human, hamster, and rat liver mitochondrial and cytosolic ALDH isozymes were used. ALDH activity was assayed by monitoring the increase in absorbance at 340 nm due to the formation of NADH when acetaldehyde was used as the substrate. The range of concentration of saidzin were: 0 - 2.4 uM. It was shown, that daidzin potently inhibited hamster and rat ALDH-2 and, as for the human enzyme, the inhibition was mixed. The daidzin Ki values for hamster and rat ALDH-2 are 0.082 and 0.052 uM, respectively, slightly higher than that for the human enzyme (0.042 uM).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:54:45 UTC 2023
Edited
by admin
on Fri Dec 15 15:54:45 UTC 2023
Record UNII
4R2X91A5M5
Record Status Validated (UNII)
Record Version
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Name Type Language
DAIDZIN
USP-RS  
Common Name English
DAIDZOSIDE
Common Name English
DAIDZEIN DAIDZIN [MI]
Common Name English
DAIDZIN (CONSTITUENT OF SOY ISOFLAVONES) [DSC]
Common Name English
DAIDZIN [USP-RS]
Common Name English
DAIDZIN (CONSTITUENT OF ASTRAGALUS) [DSC]
Common Name English
DAIDZEIN 7-O-.BETA.-D-GLUCOSIDE
Common Name English
Code System Code Type Description
CAS
552-66-9
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY
DRUG BANK
DB02115
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY
RS_ITEM_NUM
1162432
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY
WIKIPEDIA
DAIDZIN
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY
MESH
C013908
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
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CHEBI
42202
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
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EPA CompTox
DTXSID00862180
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY
PUBCHEM
107971
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY
FDA UNII
4R2X91A5M5
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY
MERCK INDEX
m4068
Created by admin on Fri Dec 15 15:54:45 UTC 2023 , Edited by admin on Fri Dec 15 15:54:45 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
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