pasireotide   

GtoPdb Ligand ID: 2018

Synonyms: pasireotide diaspartate | Signifor® | SOM 230 | SOM 320 | SOM-230
pasireotide is an approved drug (FDA and EMA (2012))
Comment: Cyclic peptide analog of somatostatin. This compound is represented on ChEMBL with slightly different stereochemistry by CHEMBL3039583.
2D Structure
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SMILES / InChI / InChIKey
Canonical SMILES NCCCCC1NC(=O)C(NC(=O)C(NC(=O)C2N(C(=O)C(NC(=O)C(NC1=O)Cc1ccc(cc1)OCc1ccccc1)Cc1ccccc1)CC(C2)OC(=O)NCCN)c1ccccc1)Cc1c[nH]c2c1cccc2
Isomeric SMILES NCCCC[C@@H]1NC(=O)[C@H](NC(=O)[C@@H](NC(=O)[C@H]2N(C(=O)[C@@H](NC(=O)[C@@H](NC1=O)Cc1ccc(cc1)OCc1ccccc1)Cc1ccccc1)C[C@@H](C2)OC(=O)NCCN)c1ccccc1)Cc1c[nH]c2c1cccc2
InChI InChI=1S/C58H66N10O9/c59-27-13-12-22-46-52(69)64-47(30-38-23-25-42(26-24-38)76-36-39-16-6-2-7-17-39)53(70)66-49(31-37-14-4-1-5-15-37)57(74)68-35-43(77-58(75)61-29-28-60)33-50(68)55(72)67-51(40-18-8-3-9-19-40)56(73)65-48(54(71)63-46)32-41-34-62-45-21-11-10-20-44(41)45/h1-11,14-21,23-26,34,43,46-51,62H,12-13,22,27-33,35-36,59-60H2,(H,61,75)(H,63,71)(H,64,69)(H,65,73)(H,66,70)(H,67,72)/t43-,46+,47+,48-,49+,50+,51+/m1/s1
InChI Key VMZMNAABQBOLAK-DBILLSOUSA-N
References
1. Cescato R, Loesch KA, Waser B, M├Ącke HR, Rivier JE, Reubi JC, Schonbrunn A. (2010)
Agonist-biased signaling at the sst2A receptor: the multi-somatostatin analogs KE108 and SOM230 activate and antagonize distinct signaling pathways.
Mol. Endocrinol., 24 (1): 240-9. [PMID:19910453]
2. Kao YJ, Ghosh M, Schonbrunn A. (2011)
Ligand-dependent mechanisms of sst2A receptor trafficking: role of site-specific phosphorylation and receptor activation in the actions of biased somatostatin agonists.
Mol. Endocrinol., 25 (6): 1040-54. [PMID:21493671]
3. Schmid HA, Schoeffter P. (2004)
Functional activity of the multiligand analog SOM230 at human recombinant somatostatin receptor subtypes supports its usefulness in neuroendocrine tumors.
Neuroendocrinology, 80 Suppl 1: 47-50. [PMID:15477717]