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Details

Stereochemistry ABSOLUTE
Molecular Formula C45H72O16
Molecular Weight 869.0436
Optical Activity UNSPECIFIED
Defined Stereocenters 26 / 26
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIOSCIN

SMILES

[H][C@]12C[C@@]3([H])[C@]4([H])CC=C5C[C@H](CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@@]6(CC[C@@H](C)CO6)O2)O[C@]7([H])O[C@H](CO)[C@@H](O[C@]8([H])O[C@@H](C)[C@H](O)[C@@H](O)[C@H]8O)[C@H](O)[C@H]7O[C@]9([H])O[C@@H](C)[C@H](O)[C@@H](O)[C@H]9O

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 869.0436
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

Tsukamoto, T.|Ueno, Y.
1
Sources: Yakugaku Zasshi (1936), 56, 802(in German 135-40). From: Chem. Zentr. 1937, I, 1438-9.

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Dioscin, a natural steroid saponin, shows remarkable protective effect against acetaminophen-induced liver damage in vitro and in vivo.
2012 Oct 2
Dioscin inhibits colon tumor growth and tumor angiogenesis through regulating VEGFR2 and AKT/MAPK signaling pathways.
2014 Dec 1
Dioscin enhances methotrexate absorption by down-regulating MDR1 in vitro and in vivo.
2014 Jun 1
Protective effects of dioscin against alcohol-induced liver injury.
2014 Mar
Patents

Patents

20050175722
1
20050220905
1

Sample Use Guides

In Vivo Use Guide
Mice 80 mg/kg/day for 21 days
Route of Administration: Oral
In Vitro Use Guide
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 Dec 16 10:55:29 UTC 2023
Edited
by admin
on Sat Dec 16 10:55:29 UTC 2023
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
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
Dioscin [WHO-DD]
Common Name English
Code System Code Type Description
FDA UNII
3B95U4OLWV
Created by admin on Sat Dec 16 10:55:29 UTC 2023 , Edited by admin on Sat Dec 16 10:55:29 UTC 2023
PRIMARY
EVMPD
SUB33941
Created by admin on Sat Dec 16 10:55:29 UTC 2023 , Edited by admin on Sat Dec 16 10:55:29 UTC 2023
PRIMARY
PUBCHEM
119245
Created by admin on Sat Dec 16 10:55:29 UTC 2023 , Edited by admin on Sat Dec 16 10:55:29 UTC 2023
PRIMARY
MERCK INDEX
m4590
Created by admin on Sat Dec 16 10:55:29 UTC 2023 , Edited by admin on Sat Dec 16 10:55:29 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID50903916
Created by admin on Sat Dec 16 10:55:29 UTC 2023 , Edited by admin on Sat Dec 16 10:55:29 UTC 2023
PRIMARY
CAS
19057-60-4
Created by admin on Sat Dec 16 10:55:29 UTC 2023 , Edited by admin on Sat Dec 16 10:55:29 UTC 2023
PRIMARY
SMS_ID
100000127804
Created by admin on Sat Dec 16 10:55:29 UTC 2023 , Edited by admin on Sat Dec 16 10:55:29 UTC 2023
PRIMARY
CHEBI
74023
Created by admin on Sat Dec 16 10:55:29 UTC 2023 , Edited by admin on Sat Dec 16 10:55:29 UTC 2023
PRIMARY
Related Record Type Details
DIOSCOREA POLYSTACHYA TUBER
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
Structure of DIOSCIN
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