linaclotide
CHEBI:68551 EXACT SEEDED enzyme inhibitor
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.
Structure
| Standard InChIKey | KXGCNMMJRFDFNR-WDRJZQOASA-N |
|---|---|
| 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](CC4=CC=C(C=C4)O)C(=O)O)C(=O)N[C@@H](CSSC[C@@H](C(=O)N3)N)C(=O)N[C@H](C(=O)N5CCC[C@H]5C(=O)N1)CC(=O)N)CC6=CC=C(C=C6)O)CCC(=O)O |
| Stereochemistry | fully defined |
| Cross-references | pubchem:16158208 |
Filing pathway
Amino acids and peptides — computed by NPClassifier npclassifier.gnps2.org@2026-09-07, which is why it is pinned rather than recomputed. The gene cluster's asserted class is ribosomal, from MIBiG.
Producer organisms 1
A claim that this taxon makes the compound. The basis says what the evidence addressed — a knockout and a database assertion are not the same claim.
| Taxon | Basis | Cluster | Evidence |
|---|---|---|---|
| Escherichia coli NCBITaxon:562 |
SOURCE_ASSERTION | mibig:BGC0000621 | PMID:2643580 |
Occurrences 1
Somebody found the compound in this organism and cited it. That is not a claim that the organism makes it, and nothing here promotes one to the other.
| Taxon | Source | Reference |
|---|---|---|
| Escherichia coli NCBITaxon:562 |
LOTUS | DOI:10.1128/IAI.57.2.645-648.1989 |
Biosynthetic gene clusters 1
| Accession | Host | Locus evidence | Genome |
|---|---|---|---|
| mibig:BGC0000621 | Escherichia coli NCBITaxon:562 |
CLUSTER_UNSTATED | genbank:M18346.1 |
A locus claim and a taxon claim are different questions. Heterologous expression settles the first and leaves the second where the isolation report left it.
Bioactivities 5
| Assay | Result | Reference |
|---|---|---|
| Primary qHTS for inhibitors of NSP2Pro chikungunya virus (CHIKV) | 3.0458 uM | pubchem.aid:1964107 |
| Primary qHTS for inhibitors of SARS-S pseudo-typed particle cell entry | 19.9526 uM | pubchem.aid:1479145 |
| Human Guanylyl cyclase-C (Receptor Guanylyl Cyclase (RGC) family) | ACTIVE | PMID:17694454 |
| Human Guanylyl cyclase-C (Receptor Guanylyl Cyclase (RGC) family) | ACTIVE | PMID:20863829 |
| Rat Guanylyl cyclase-C (Receptor Guanylyl Cyclase (RGC) family) | ACTIVE | PMID:20863829 |
Provenance
| Source concept | Source | Version |
|---|---|---|
| BGC0000621 | MIBIG | 3 |
| CHEBI:68551 | CHEBI | 3-star |
This page is generated from data/natural_products/amino_acids_and_peptides/linaclotide.yaml, which is generated from the committed inventories. Neither is edited by hand.