U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C45H72O16
Molecular Weight 869.0453
Optical Activity UNSPECIFIED
Defined Stereocenters 26 / 26
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIOSCIN

SMILES

C[C@]1([H])CC[C@@]2([C@@]([H])(C)[C@@]3([H])[C@]([H])(C[C@@]4([H])[C@]5([H])CC=C6C[C@]([H])(CC[C@]6(C)[C@@]5([H])CC[C@@]43C)O[C@@]7([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O7)O[C@@]8([H])[C@@]([H])([C@@]([H])([C@]([H])([C@]([H])(C)O8)O)O)O)O)O[C@@]9([H])[C@@]([H])([C@@]([H])([C@]([H])([C@]([H])(C)O9)O)O)O)O2)OC1

InChI

InChIKey=VNONINPVFQTJOC-ZGXDEBHDSA-N
InChI=1S/C45H72O16/c1-19-9-14-45(54-18-19)20(2)30-28(61-45)16-27-25-8-7-23-15-24(10-12-43(23,5)26(25)11-13-44(27,30)6)57-42-39(60-41-36(52)34(50)32(48)22(4)56-41)37(53)38(29(17-46)58-42)59-40-35(51)33(49)31(47)21(3)55-40/h7,19-22,24-42,46-53H,8-18H2,1-6H3/t19-,20+,21+,22+,24+,25-,26+,27+,28+,29-,30+,31+,32+,33-,34-,35-,36-,37+,38-,39-,40+,41+,42-,43+,44+,45-/m1/s1

HIDE SMILES / InChI

Molecular Formula C45H72O16
Molecular Weight 869.0453
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 25 / 26
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/25993784 | https://www.ncbi.nlm.nih.gov/pubmed/28796245 | https://www.ncbi.nlm.nih.gov/pubmed/28849197 | https://www.ncbi.nlm.nih.gov/pubmed/28435431

Dioscin is a natural steroid saponin derived from several plants, showing the potent anti-cancer effect against a variety of tumor cell lines. Pharmacological studies have shown that dioscin processes anti-cerebral ischemia/reperfusion injury, anti-liver fibrosis and anti-obesity effects. Dioscin markedly inhibited cell viability, colony formation, motility and induced apoptosis in prostate cancer cells. Dioscin remarkably suppressed the migratory and invasive capacities of melanoma cells. In preclinical models, dioscin showed significant anti-metastatic effects and suppress the tumor cell malignancy.

Originator

Sources: Yakugaku Zasshi (1936), 56, 802(in German 135-40). From: Chem. Zentr. 1937, I, 1438-9.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Dioscin inhibits colon tumor growth and tumor angiogenesis through regulating VEGFR2 and AKT/MAPK signaling pathways.
2014 Dec 1
Patents

Sample Use Guides

Mice 80 mg/kg/day for 21 days
Route of Administration: Oral
The PC3 cells were seeded in 96-well plates (5000 cells/well) in DMEM/F12 medium and incubated overnight, and the PC3 cell-derived mammospheres were seeded in growth medium for 5 days culturing. Subsequently, various concentrations of dioscin (0.18–92 μM for PC3 monolayers; 0.36–184 μM for mammospheres) were added in each well. After PC3 cells were incubated for 24 h, the cell viability was analyzed using the MTT assay kit
Substance Class Chemical
Created
by admin
on Sat Jun 26 01:30:32 UTC 2021
Edited
by admin
on Sat Jun 26 01:30:32 UTC 2021
Record UNII
3B95U4OLWV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIOSCIN
MI  
Common Name English
.BETA.-D-GLUCOPYRANOSIDE, (3.BETA.,25R)-SPIROST-5-EN-3-YL O-6- DEOXY-ALPHA-L-MANNOPYRANOSYL-(1->2)-O-(6-DEOXY-.ALPHA.-L- MANNOPYRANOSYL-(1->4))-
Systematic Name English
POLYPHYLLIN III
Common Name English
DIOSCINE
Common Name English
DIOSCIN [WHO-DD]
Common Name English
(+)-DIOSCIN
Common Name English
(3.BETA.,25R)-SPIROST-5-EN-3-YL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->2)-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->4))-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
DIOSGENIN 3-O-.ALPHA.-L-RHAMNOPYRANOSYL-(1->2)-(.ALPHA.-L-RHAMNOPYRANOSYL-(1->4))-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
COLLETTISIDE III
Common Name English
PARIS III
Common Name English
DIOSCIN [MI]
Common Name English
Code System Code Type Description
FDA UNII
3B95U4OLWV
Created by admin on Sat Jun 26 01:30:32 UTC 2021 , Edited by admin on Sat Jun 26 01:30:32 UTC 2021
PRIMARY
EVMPD
SUB33941
Created by admin on Sat Jun 26 01:30:32 UTC 2021 , Edited by admin on Sat Jun 26 01:30:32 UTC 2021
PRIMARY
PUBCHEM
119245
Created by admin on Sat Jun 26 01:30:32 UTC 2021 , Edited by admin on Sat Jun 26 01:30:32 UTC 2021
PRIMARY
MERCK INDEX
M4590
Created by admin on Sat Jun 26 01:30:32 UTC 2021 , Edited by admin on Sat Jun 26 01:30:32 UTC 2021
PRIMARY Merck Index
CAS
19057-60-4
Created by admin on Sat Jun 26 01:30:32 UTC 2021 , Edited by admin on Sat Jun 26 01:30:32 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
ACTIVE MOIETY