YM-254890   

GtoPdb Ligand ID: 9335

Synonyms: YM254890
Comment: The natural product YM-254890 from Chromobacterium sp. QS3666 is a selective inhibitor of Gq signalling. The first total synthesis of this and analogues with SAR are reported [1]. Note that PubChem substances with assay results are indexed in the Nature Chemistry article. An earlier PDB entry 3AH8 shows a bovine G-protein complex with YM-254890.
2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 22
Hydrogen bond donors 5
Rotatable bonds 15
Topological polar surface area 285.69
Molecular weight 959.49
XLogP 2.07
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Canonical SMILES COC(C1C(=O)OC(C)C(NC(=O)C)C(=O)OC(Cc2ccccc2)C(=O)N(C)C(=C)C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)N1C)C(C(C)C)OC(=O)C(C(C(C)C)O)NC(=O)C)C)C)C)C
Isomeric SMILES CO[C@@H]([C@H]1C(=O)O[C@H](C)[C@H](NC(=O)C)C(=O)O[C@H](Cc2ccccc2)C(=O)N(C)C(=C)C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N1C)[C@@H](C(C)C)OC(=O)[C@H]([C@@H](C(C)C)O)NC(=O)C)C)C)C)C
InChI InChI=1S/C46H69N7O15/c1-22(2)37(56)34(49-30(11)55)45(63)68-38(23(3)4)35-43(61)53(14)36(28(9)65-15)46(64)66-27(8)33(48-29(10)54)44(62)67-32(21-31-19-17-16-18-20-31)42(60)52(13)25(6)39(57)47-24(5)41(59)51(12)26(7)40(58)50-35/h16-20,22-24,26-28,32-38,56H,6,21H2,1-5,7-15H3,(H,47,57)(H,48,54)(H,49,55)(H,50,58)/t24-,26-,27+,28+,32+,33-,34-,35-,36-,37+,38+/m0/s1
InChI Key QVYLWCAYZGFGNF-WBWCVGBTSA-N
References
1. Xiong, XF et al.
Total synthesis and structure activity relationship studies of a series of selective G protein inhibitors.
Accessed on 12/10/2016. Modified on 12/10/2016. Nat Chem, advance publication July 2016), http://www.nature.com/nchem/journal/vaop/ncurrent/full/nchem.2577.html