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Details

Stereochemistry ABSOLUTE
Molecular Formula C39H62O12
Molecular Weight 722.9024
Optical Activity UNSPECIFIED
Defined Stereocenters 22 / 22
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OPHIOPOGONIN B

SMILES

C[C@H]1[C@H]2[C@H](C[C@H]3[C@@H]4CC=C5C[C@@H](O)C[C@@H](O[C@@H]6O[C@H](C)[C@H](O)[C@H](O)[C@H]6O[C@@H]7O[C@@H](C)[C@H](O)[C@@H](O)[C@H]7O)[C@]5(C)[C@H]4CC[C@]23C)O[C@]18CC[C@@H](C)CO8

InChI

InChIKey=OWGURJWJHWYCIQ-AKYREZHBSA-N
InChI=1S/C39H62O12/c1-17-9-12-39(46-16-17)18(2)28-26(51-39)15-25-23-8-7-21-13-22(40)14-27(38(21,6)24(23)10-11-37(25,28)5)49-36-34(32(44)30(42)20(4)48-36)50-35-33(45)31(43)29(41)19(3)47-35/h7,17-20,22-36,40-45H,8-16H2,1-6H3/t17-,18+,19+,20-,22-,23-,24+,25+,26+,27-,28+,29+,30+,31-,32+,33-,34-,35+,36+,37+,38+,39-/m1/s1

HIDE SMILES / InChI

Molecular Formula C39H62O12
Molecular Weight 722.9024
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 22 / 22
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Ophiopogonin B is a glycosid (saponin) isolated from the butanol-soluble fraction of the fresh subterranean part of Ophiopogon japonicus, which is often used in Chinese traditional medicine to treat pulmonary disease and cancer. Ophiopogonin B was tested against non-small cell lung carcinoma, cervical cancer and gastric cancer cell lines, demonstrating inhibition of PI3K-Akt and mTOR-Akt signaling.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Oral
In Vitro Use Guide
NSCLC cell lines (Human non-small cell lung cancer cells lines A549, NCI-H460, NCI-H157, H1299, H1792-2, H1944, NCI-226, H358, H292-G, Hop62, and H522) were treated with ophiopogonin B at concentration 10 umol/l from 24 to 72 hours. After 72 h of treatment, OP-B significantly decreased cell viability of all cell lines tested in a dose-dependent manner, and the IC50 was <4 umol/l (~3.87 umol/l) hours. High concentrations of OP‑B (5, 10 and 20 umol/l) exerted potent antiproliferative effects on SGC‑7901 cells in a dose‑dependent manner.
Substance Class Chemical
Record UNII
S18059B04U
Record Status Validated (UNII)
Record Version