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))
Compound class: Peptide
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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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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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
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
Search Google for chemical match using the InChIKey NSPHQWLKCGGCQR-DLJDZFDSSA-N
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UniChem Compound Search for chemical match using the InChIKey NSPHQWLKCGGCQR-DLJDZFDSSA-N
UniChem Connectivity Search for chemical match using the InChIKey NSPHQWLKCGGCQR-DLJDZFDSSA-N