Colibactin

Colibactin
Names
	IUPAC name 2-[6-[(2S)-2-methyl-3,4-dihydro-2H-pyrrol-5-yl]-5-oxo-4-azaspiro[2.4]hept-6-en-7-yl]-N-[[4-[2-[4-[2-[[2-[6-[(2S)-2-methyl-3,4-dihydro-2H-pyrrol-5-yl]-5-oxo-4-azaspiro[2.4]hept-6-en-7-yl]acetyl]amino]acetyl]-1,3-thiazol-2-yl]-2-oxoacetyl]-1,3-thiazol-2-yl]methyl]acetamide
Identifiers
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:156303;
ChemSpider	115010508;
KEGG	C22668;
PubChem CID	138805674;
CompTox Dashboard (EPA)	DTXSID501336855 ;
	InChI InChI=1S/C37H38N8O7S2/c1-17-3-5-21(40-17)29-19(36(7-8-36)44-33(29)51)11-26(47)38-13-25(46)23-15-54-35(43-23)32(50)31(49)24-16-53-28(42-24)14-39-27(48)12-20-30(22-6-4-18(2)41-22)34(52)45-37(20)9-10-37/h15-18H,3-14H2,1-2H3,(H,38,47)(H,39,48)(H,44,51)(H,45,52)/t17-,18-/m0/s1 Key: ZWKHDAZPVITMAI-ROUUACIJSA-N;
	SMILES C[C@H]1CCC(=N1)C2=C(C3(CC3)NC2=O)CC(=O)NCC4=NC(=CS4)C(=O)C(=O)C5=NC(=CS5)C(=O)CNC(=O)CC6=C(C(=O)NC67CC7)C8=N[C@H](CC8)C;
Properties
Chemical formula	C37H38N8O7S2
Molar mass	770.88 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Colibactin is a genotoxic metabolite produced by Escherichia coli and other Enterobacteriaceae. Colibactin is a polyketide peptide that can form inter-strand crosslinks in DNA.^[1] Colibactin forms DNA inter-strand cross-links by alkylation of adenine moieties on opposing DNA strands.^[2] It induces lytic development in certain bacteria that contain prophages.^[3] Colibactin is only produced by bacterial strains containing a polyketide synthase genomic island (pks)^[4] or clb biosynthetic gene cluster.^[2] About 20% of humans in high-income countries are colonized with E. coli that harbor the pks island.^[5]^[6]

References