OPHIOPOGONIN B

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 Search

SMILES

[H][C@]12C[C@@]3([H])[C@]4([H])CC=C5C[C@@H](O)C[C@@H](O[C@]6([H])O[C@H](C)[C@H](O)[C@H](O)[C@H]6O[C@]7([H])O[C@@H](C)[C@H](O)[C@@H](O)[C@H]7O)[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]8(CC[C@@H](C)CO8)O2

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

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	21 / 22
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8477511 | https://www.ncbi.nlm.nih.gov/pubmed/23151908 | https://www.ncbi.nlm.nih.gov/pubmed/27121658

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 Target	Pharmacology	Condition	Potency
PI3K-Akt signaling pathway 24 Target ID: map04151 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23151908	Inhibitor 8297
mTOR signaling pathway 7 Target ID: map04150 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23984518	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Non-small cell lung cancer 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23151908	Primary	Basic research	Unknown Approved Use Unknown
Cervical cancer 40 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23984518	Primary	Basic research	Unknown Approved Use Unknown
Gastric cancer 53 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27121658	Primary	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Ophiopogonin B-induced autophagy in non-small cell lung cancer cells via inhibition of the PI3K/Akt signaling pathway.	2013 Feb	23151908
[Molecular mechanism of ophiopogonin B induced cellular autophagy of human cervical cancer HeLa cells].	2013 Jun	23984518
Effects of ophiopogonin B on the proliferation and apoptosis of SGC‑7901 human gastric cancer cells.	2016 Jun	27121658

Patents

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 Created by `admin` on `Fri Dec 15 15:59:43 GMT 2023` Edited by `admin` on `Fri Dec 15 15:59:43 GMT 2023`
Record UNII	S18059B04U
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OPHIOPOGONIN B

Common Name

English

PROSAPOGENIN D3

Common Name

English

.BETA.-D-GALACTOPYRANOSIDE, (1.BETA.,3.BETA.,25R)-3-HYDROXYSPIROST-5-EN-1-YL 6-DEOXY-2-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)-

Common Name

English

(-)-OPHIOPOGONIN B

Common Name

English

Code System Code Type Description

FDA UNII

S18059B04U