plecanatide   

GtoPdb Ligand ID: 9069

Synonyms: [3-glutamic acid(D>E)]human uroguanylin | SP-304 | Trulance®
plecanatide is an approved drug (FDA (2017))
Comment: Plecanatide is a synthetic analogue of uroguanylin, which is an agonist of the guanylate cyclase C (GC-C) receptor (GUCY2C) [3]. Activation of GC-C in mucosal epithelial cells of the gastrointestinal (GI) tract causes the secretion of fluid, facilitating bowel movements. Plecanatide has potential to help manage constipating GI disorders, such as chronic idiopathic constipation and constipation-predominant irritable bowel syndrome (IBS-C). Plecanatide is one of the peptides claimed in patent WO2014151206, where it is represented by SEQ ID NO: 1 and code SP-304, with residue 3 (Aad) being gultamic acid (E, Glu) [2].
The SMILES and structure image used in this entry are from Chemicalize.
HELM notation is PEPTIDE1{N.D.E.C.E.L.C.V.N.V.A.C.T.G.C.L}$PEPTIDE1,PEPTIDE1,12:R3-4:R3|PEPTIDE1,PEPTIDE1,15:R3-7:R3$$$.
linaclotide was the first GC-C activator to reach the clinic, like plecanatide it is approved for the treatment of chronic constipation and IBS-C.
2D Structure
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SMILES / InChI / InChIKey
Canonical SMILES OC(=O)CCC1NC(=O)C(CSSCC2NC(=O)C(C)NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC1=O)CC(C)C)CSSCC(NC(=O)CNC(=O)C(NC2=O)C(O)C)C(=O)NC(C(=O)O)CC(C)C)C(C)C)CC(=O)N)C(C)C)NC(=O)C(NC(=O)C(NC(=O)C(CC(=O)N)N)CC(=O)O)CCC(=O)O
Isomeric SMILES OC(=O)CC[C@@H]1NC(=O)[C@H](CSSC[C@@H]2NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)CC(C)C)CSSC[C@H](NC(=O)CNC(=O)[C@@H](NC2=O)[C@H](O)C)C(=O)N[C@H](C(=O)O)CC(C)C)C(C)C)CC(=O)N)C(C)C)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(=O)N)N)CC(=O)O)CCC(=O)O
InChI InChI=1S/C65H104N18O26S4/c1-25(2)15-34-55(98)80-41-24-113-110-21-38(58(101)77-37(65(108)109)16-26(3)4)71-44(87)20-69-62(105)50(30(10)84)83-61(104)40(78-51(94)29(9)70-63(106)48(27(5)6)81-57(100)35(18-43(68)86)76-64(107)49(28(7)8)82-60(41)103)23-112-111-22-39(59(102)73-32(53(96)75-34)11-13-45(88)89)79-54(97)33(12-14-46(90)91)72-56(99)36(19-47(92)93)74-52(95)31(66)17-42(67)85/h25-41,48-50,84H,11-24,66H2,1-10H3,(H2,67,85)(H2,68,86)(H,69,105)(H,70,106)(H,71,87)(H,72,99)(H,73,102)(H,74,95)(H,75,96)(H,76,107)(H,77,101)(H,78,94)(H,79,97)(H,80,98)(H,81,100)(H,82,103)(H,83,104)(H,88,89)(H,90,91)(H,92,93)(H,108,109)/t29-,30+,31-,32-,33-,34-,35-,36-,37-,38-,39-,40-,41-,48-,49-,50-/m0/s1
InChI Key NSPHQWLKCGGCQR-DLJDZFDSSA-N