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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H14O5
Molecular Weight 286.2794
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOSAKURANETIN

SMILES

COC1=CC=C(C=C1)[C@@H]2CC(=O)C3=C(O)C=C(O)C=C3O2

InChI

InChIKey=HMUJXQRRKBLVOO-AWEZNQCLSA-N
InChI=1S/C16H14O5/c1-20-11-4-2-9(3-5-11)14-8-13(19)16-12(18)6-10(17)7-15(16)21-14/h2-7,14,17-18H,8H2,1H3/t14-/m0/s1

HIDE SMILES / InChI

Molecular Formula C16H14O5
Molecular Weight 286.2794
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Isosakuranetin is a citrus fruit flavanone. It is a TRPM3 channel blocker and CYP1 enzyme isoforms inhibitor. It is a strong candidate, as chemopreventive food ingredient against CYP1B1-related carcinogenesis. Isosakuranetin may be useful in treating neuropathic pain without body temperature increase. Isosakuranetin attenuated ethanol-induced gastritis by inhibiting the infiltration of immune cells, including neutrophils, via the regulation of CXCL4 (or IL-8) secretion and the activation NF-κB.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
50.0 nM [IC50]
2.2 µM [IC50]
3.1 µM [IC50]
1.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Preventing
Unknown
Preventing
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Mice: 2 or 10 mg/kg
Route of Administration: Intraperitoneal
In Vitro Use Guide
Isosakuranetin blocked the inward TRPM3 currents at -113 mV slightly more potently (IC50 = 80 nM) compared with the outward TRPM currents measured at -87 mV (IC50 = 120 nM). Both currents were isosakuranetin sensitive and almost completely blocked at a concentration of 3 uM.
Substance Class Chemical
Record UNII
U02X7TF8UA
Record Status Validated (UNII)
Record Version