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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=CC3=C(C=C2)C(=O)C(=CO3)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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Primary TargetPharmacologyConditionPotency
80.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
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
Record UNII
4R2X91A5M5
Record Status Validated (UNII)
Record Version