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Details

Stereochemistry ABSOLUTE
Molecular Formula C45H73NO15
Molecular Weight 868.0588
Optical Activity UNSPECIFIED
Defined Stereocenters 26 / 26
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SOLAMARGINE

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)CN6)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=MBWUSSKCCUMJHO-ZGXDEBHDSA-N
InChI=1S/C45H73NO15/c1-19-9-14-45(46-17-19)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(53)34(51)32(49)22(4)56-41)37(54)38(29(18-47)58-42)59-40-35(52)33(50)31(48)21(3)55-40/h7,19-22,24-42,46-54H,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 C45H73NO15
Molecular Weight 868.0588
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 25 / 26
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27830724

Solamargine is the one of major compounds of Solanum lycocarpum- fruit glycoalkaloid extract, and a major steroidal alkaloid glycoside, which is purified from Solanum nigrum L (SNL), a traditional Chinese medicinal herb. It has been shown that solamargine has anti-tumor activity against the several types of cancers. Also as a part of SR-T100 Gel solamargine in the phase II of clinical trial for the treatment of Actinic Keratosis and Bowen's Disease. The precise mechanism of its actions is still undefined, but existed several potential pathways. In case of castration-resistant prostate cancer cells, solamargine inhibits the growth cells through AMPKalpha-mediated inhibition of p65, followed by reduction of MUC1 expression in vitro and in vivo. In case of lung cancer cells solamargine inhibits the growth cells through reduction of EP4 protein expression, followed by increasing ERK1/2 phosphorylation. The inter-correlations between EP4, DNA methyltransferase 1 (DNMT1) and c-Jun and feedback regulation of ERK1/2 by c-Jun contribute to the overall responses of solamargine in this process.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Solamargine induces apoptosis and sensitizes breast cancer cells to cisplatin.
2007 Nov
A lysosomal-mitochondrial death pathway is induced by solamargine in human K562 leukemia cells.
2010 Sep
Patents

Patents

Sample Use Guides

patients with dvanced solid tumors: coramsine (mixture of solasonine and solamargine): 1.0 mg/kg/day over 2 hours or 1.5 mg/kg/day over 4 hours Actinic Keratosis; Bowen's Disease: SR-T100 Gel containing 2.3% of solamargine in Solanum undatum extract: is used once daily with occlusive dressing for 16 weeks.
Route of Administration: Other
Solamargine inhibited the growth of two castration-resistant prostate cancer (CRPC) cell lines (PC3 and DU145) in the dose-dependent manner with significant effect observed at 6 to 8 μM for up to 72 h. The IC50 were 7.0 and 6.5 μM in 24 h in PC3 and DU145 cells, respectively. No further inhibitory effects were observed with higher doses of solamargine. This inhibition takes place through AMPKα-mediated inhibition of p65, followed by reduction of MUC1 expression.
Substance Class Chemical
Created
by admin
on Sat Dec 16 06:18:00 GMT 2023
Edited
by admin
on Sat Dec 16 06:18:00 GMT 2023
Record UNII
8KG991E7BN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SOLAMARGINE
Common Name English
BETA.-D-GLUCOPYRANOSIDE, (3.BETA.,22.ALPHA.,25R)-SPIROSOL-5-EN-3-YL O-6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->2)-O-(6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL-(1->4))-
Common Name English
.DELTA.-SOLANIGRINE
Common Name English
SOLAMARGINE, (-)-
Common Name English
.ALPHA.-SOLAMARGINE
Common Name English
NSC-407810
Code English
(-)-SOLAMARGINE
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 211705
Created by admin on Sat Dec 16 06:18:00 GMT 2023 , Edited by admin on Sat Dec 16 06:18:00 GMT 2023
FDA ORPHAN DRUG 211805
Created by admin on Sat Dec 16 06:18:00 GMT 2023 , Edited by admin on Sat Dec 16 06:18:00 GMT 2023
Code System Code Type Description
DRUG BANK
DB12700
Created by admin on Sat Dec 16 06:18:00 GMT 2023 , Edited by admin on Sat Dec 16 06:18:00 GMT 2023
PRIMARY
WIKIPEDIA
SOLAMARGINE
Created by admin on Sat Dec 16 06:18:00 GMT 2023 , Edited by admin on Sat Dec 16 06:18:00 GMT 2023
PRIMARY
FDA UNII
8KG991E7BN
Created by admin on Sat Dec 16 06:18:00 GMT 2023 , Edited by admin on Sat Dec 16 06:18:00 GMT 2023
PRIMARY
NSC
407810
Created by admin on Sat Dec 16 06:18:00 GMT 2023 , Edited by admin on Sat Dec 16 06:18:00 GMT 2023
PRIMARY
EPA CompTox
DTXSID00942456
Created by admin on Sat Dec 16 06:18:00 GMT 2023 , Edited by admin on Sat Dec 16 06:18:00 GMT 2023
PRIMARY
CAS
20311-51-7
Created by admin on Sat Dec 16 06:18:00 GMT 2023 , Edited by admin on Sat Dec 16 06:18:00 GMT 2023
PRIMARY
PUBCHEM
73611
Created by admin on Sat Dec 16 06:18:00 GMT 2023 , Edited by admin on Sat Dec 16 06:18:00 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY