plecanatide   Click here for help

GtoPdb Ligand ID: 9069

Synonyms: [3-glutamic acid(D>E)]human uroguanylin | SP-304 | Trulance®
Approved drug
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
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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
Classification Click here for help
Compound class Peptide or derivative
Approved drug? Yes (FDA (2017))
International Nonproprietary Names Click here for help
INN number INN
9367 plecanatide
Synonyms Click here for help
[3-glutamic acid(D>E)]human uroguanylin | SP-304 | Trulance®
Database Links Click here for help
ChEMBL Ligand CHEMBL2103867
DrugCentral Ligand 5208
GtoPdb PubChem SID 315661154
PubChem CID 70693500
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