FR-49175   

GtoPdb Ligand ID: 3150

Synonyms: AC1L4YI4 | bis(methylthio)gliotoxin | dimethylgliotoxin | FR 49175
Comment: FR-49175 is a toxic metabolite with anthiphagocytic and immunosuppressive properties synthesised by fungi such as Aspergillus fumigatus. It is an analog of a gliotoxin known to inhibit PAF-induced platelet aggregation.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 131.68
Molecular weight 356.09
XLogP -1.09
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES CSC12CC3=CC=CC(C3N2C(=O)C(N(C1=O)C)(SC)CO)O
Isomeric SMILES CS[C@]12CC3=CC=C[C@@H]([C@H]3N2C(=O)[C@](N(C1=O)C)(SC)CO)O
InChI InChI=1S/C15H20N2O4S2/c1-16-12(20)14(22-2)7-9-5-4-6-10(19)11(9)17(14)13(21)15(16,8-18)23-3/h4-6,10-11,18-19H,7-8H2,1-3H3/t10-,11-,14+,15+/m0/s1
InChI Key OVBAGMZLGLXSBN-UOVKNHIHSA-N
Classification
Compound class Natural product or derivative
IUPAC Name
(3R,5aS,6S,10aR)-6-hydroxy-3-(hydroxymethyl)-2-methyl-3,10a-bis(methylsulfanyl)-1H,2H,3H,4H,5aH,6H,10H,10aH-piperazino[1,2-a]indole-1,4-dione
Synonyms
AC1L4YI4 | bis(methylthio)gliotoxin | dimethylgliotoxin | FR 49175
Database Links
CAS Registry No. 74149-38-5 (source: Scifinder)
ChEMBL Ligand CHEMBL1088981
GtoPdb PubChem SID 178100262
PubChem CID 194564
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