linaclotide   Click here for help

GtoPdb Ligand ID: 5017

Synonyms: Constella® | Linzess® | MM-416775
Approved drug
linaclotide is an approved drug (FDA and EMA (2012))
Compound class: Peptide
Comment: Linaclotide represents a first-in-class, oral guanylate cyclase 2C activator [2]. It is a synthetic analogue of pathological heat-stable bacterial enterotoxins, and retains the same intrachain disulfide bond structure essential for biological activity.
Marketed formulations contain linaclotide acetate (PubChem CID 16158207). See also plecanatide, the second approved GC-C activator.
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2D Structure
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SMILES / InChI / InChIKey
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Canonical SMILES OC(=O)CC[C@@H]1NC(=O)[C@@H]2CSSC[C@@H]3NC(=O)[C@H](C)NC(=O)[C@H]4N(C(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H](NC1=O)Cc1ccc(cc1)O)CSSC[C@H](NC(=O)CNC(=O)[C@@H](NC3=O)[C@H](O)C)C(=O)N[C@H](C(=O)O)Cc1ccc(cc1)O)CSSC[C@@H](C(=O)N2)N)CC(=O)N)CCC4
Isomeric SMILES C[C@H]1C(=O)N[C@H]2CSSC[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSSC[C@H](NC(=O)CNC(=O)[C@@H](NC2=O)[C@@H](C)O)C(=O)N[C@@H](Cc2ccc(cc2)O)C(=O)O)C(=O)N[C@@H](CSSC[C@@H](C(=O)N3)N)C(=O)N[C@H](C(=O)N2CCC[C@H]2C(=O)N1)CC(=O)N)Cc1ccc(cc1)O)CCC(=O)O
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
InChI Key KXGCNMMJRFDFNR-WDRJZQOASA-N