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CHEBI:68551 - linaclotide

ChEBI IDCHEBI:68551
ChEBI Namelinaclotide
Stars
DefinitionA 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.
Last Modified22 February 2017
SubmitterSteve
DownloadsMolfile
FormulaC59H79N15O21S6
Net Charge0
Average Mass1526.767
Monoisotopic Mass1525.38992
SMILES[H][C@@]1(C(=O)N[C@@H](Cc2ccc(O)cc2)C(=O)O)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
InChIInChI=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
InChIKeyKXGCNMMJRFDFNR-WDRJZQOASA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
guanylate cyclase 2C agonist  An agonist that selectively binds to and activates guanylate cyclase 2C receptors.
ChEBI Ontology
Outgoing Relation(s)
linaclotide (CHEBI:68551) has role guanylate cyclase 2C agonist (CHEBI:68553)
linaclotide (CHEBI:68551) is a heterodetic cyclic peptide (CHEBI:24533)
Synonyms  Source
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
Cys Cys Glu Tyr Cys Cys Asn Pro Ala Cys Thr Gly Cys Tyr (disulfide bridge: 1-6; 2-10; 5-13)KEGG DRUG
Brand Name  Source
LinzessChemIDplus
Manual XrefsDatabases
D09355KEGG DRUG
LinaclotideWikipedia
WO2012021715Patent
MX2012001660Patent
Registry NumbersSources
CAS:851199-59-2KEGG DRUG
CAS:851199-59-2ChemIDplus
Citations