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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H20O11
Molecular Weight 448.3769
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISOORIENTIN

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C2=C(O)C=C3OC(=CC(=O)C3=C2O)C4=CC=C(O)C(O)=C4

InChI

InChIKey=ODBRNZZJSYPIDI-VJXVFPJBSA-N
InChI=1S/C21H20O11/c22-6-14-17(27)19(29)20(30)21(32-14)16-11(26)5-13-15(18(16)28)10(25)4-12(31-13)7-1-2-8(23)9(24)3-7/h1-5,14,17,19-24,26-30H,6H2/t14-,17-,19+,20-,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H20O11
Molecular Weight 448.3769
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

Isoorientin is a common C-glycosyl flavone in the human diet. It has been isolated from several plant species, including Phyllostachys pubescens, Crataegus monogyna and Crataegus pentagyna, Patrinia villosa Juss, Drosophyllum lusitanicum, buckwheat, Arum palaestinum, and Rumex and Swertia. Isoorientin possesses significant anti-nociceptive and anti-inflammatory activities. Significantly protected PC12 nerve cells from 6-OHDA-induced apoptotic neurotoxicity and reduced the proliferation of HepG2 cells. Isoorientin showed anti-RSV (respiratory syncytial virus) activity.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
19.7 µM [IC50]
39.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Mice: 10 or 20 mg/Kg body weight
Route of Administration: Intraperitoneal
In Vitro Use Guide
Isoorientin was active as quorum sensing (QS) inhibitor when tested on the E. coli biosensor model. It presented moderate activity - 45 ug/disc. The result of QS inhibition assay with Isoorientin using C.violaceum as biosensor was - 40 ug/disc.
Substance Class Chemical
Record UNII
A37342TIX1
Record Status Validated (UNII)
Record Version