CHEBI:68551 - linaclotide

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ChEBI Name linaclotide ChEBI ID CHEBI:68551 Definition A fourteen-membered heterodetic cyclic peptide consisting of Cys, Cys, Glu, Tyr, Cys, Cys, Asn, Pro, Ala, Cys, Thr, Gly, Cys and Tyr residues joined in sequence and cyclised by three disulfide bonds: between Cys1 and Cys6, between Cys2 and Cys10, and between Cys5 and Cys13. Used for treatment of irritable bowel syndrome accompanied by constipation. Stars This entity has been manually annotated by the ChEBI Team. Supplier Information Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Wikipedia License Read full article at Wikipedia Formula C59H79N15O21S6 Net Charge 0 Average Mass 1526.73600 Monoisotopic Mass 1525.38992 InChI InChI=1S/C59H79N15O21S6/c1-26-47(82)69-41-25-101-99-22-38-52(87)65-33(13-14-45(80)81)49(84)66-34(16-28-5-9-30(76)10-6-28)50(85)71-40(54(89)72-39(23-97-96-20-32(60)48(83)70-38)53(88)67-35(18-43(61)78)58(93)74-15-3-4-42(74)56(91)63-26)24-100-98-21-37(64-44(79)19-62-57(92)46(27(2)75)73-55(41)90)51(86)68-36(59(94)95)17-29-7-11-31(77)12-8-29/h5-12,26-27,32-42,46,75-77H,3-4,13-25,60H2,1-2H3,(H2,61,78)(H,62,92)(H,63,91)(H,64,79)(H,65,87)(H,66,84)(H,67,88)(H,68,86)(H,69,82)(H,70,83)(H,71,85)(H,72,89)(H,73,90)(H,80,81)(H,94,95)/t26-,27+,32-,33-,34-,35-,36-,37-,38-,39-,40-,41-,42-,46-/m0/s1 InChIKey KXGCNMMJRFDFNR-WDRJZQOASA-N SMILES [H][C@]1(CSSC[C@]2([H])NC(=O)[C@H](Cc3ccc(O)cc3)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H]3CSSC[C@H](NC(=O)[C@H](C)NC(=O)[C@@H]4CCCN4C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CSSC[C@H](N)C(=O)N3)NC2=O)C(=O)N[C@@]([H])([C@@H](C)O)C(=O)NCC(=O)N1)C(=O)N[C@@H](Cc1ccc(O)cc1)C(O)=O Roles Classification Chemical Role(s): Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Biological Role(s): guanylate cyclase 2C agonist An agonist that selectively binds to and activates guanylate cyclase 2C receptors. View more via ChEBI Ontology ChEBI Ontology Outgoing linaclotide (CHEBI:68551) has role guanylate cyclase 2C agonist (CHEBI:68553) linaclotide (CHEBI:68551) is a heterodetic cyclic peptide (CHEBI:24533) Synonyms Sources Cys Cys Glu Tyr Cys Cys Asn Pro Ala Cys Thr Gly Cys Tyr (disulfide bridge: 1-6; 2-10; 5-13) KEGG DRUG L-cysteinyl-L-cysteinyl-L-α-glutamyl-L-tyrosyl-L-cysteinyl-L-cysteinyl-L-asparaginyl-L-prolyl-L-alanyl-L-cysteinyl-L-threonylglycyl-L-cysteinyl-L-tyrosine cyclic (1→6),(2→10),(5→13)-tris(disulfide) ChemIDplus Brand Name Source Linzess ChemIDplus Manual Xrefs Databases D09355 KEGG DRUG Linaclotide Wikipedia MX2012001660 Patent WO2012021715 Patent View more database links Registry Numbers Types Sources 851199-59-2 CAS Registry Number KEGG DRUG 851199-59-2 CAS Registry Number ChemIDplus Citations Types Sources 19706070 PubMed citation Europe PMC 20307554 PubMed citation Europe PMC 20377786 PubMed citation Europe PMC 20560145 PubMed citation Europe PMC 20863829 PubMed citation Europe PMC 21185863 PubMed citation Europe PMC 21205879 PubMed citation Europe PMC 21382586 PubMed citation Europe PMC 21446888 PubMed citation Europe PMC 21616041 PubMed citation Europe PMC 21651347 PubMed citation Europe PMC 21830967 PubMed citation Europe PMC 22045908 PubMed citation Europe PMC 22114754 PubMed citation Europe PMC 22114756 PubMed citation Europe PMC 22149576 PubMed citation Europe PMC 22462039 PubMed citation Europe PMC 22553939 PubMed citation Europe PMC 22807692 PubMed citation Europe PMC 22918691 PubMed citation Europe PMC 22986437 PubMed citation Europe PMC 22986440 PubMed citation Europe PMC Last Modified 22 February 2017