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CHEBI:156303 - colibactin

ChEBI IDCHEBI:156303
ChEBI Namecolibactin
Stars
DefinitionA member of the class of 1,3-thiazoles that comprises of two units of 2-[(2-{6-[(2S)-2-methyl-3,4-dihydro-2H-pyrrol-5-yl]-5-oxo-4-azaspiro[2.4]hept-6-en-7-yl}acetamido)methyl]-1,3-thiazole-4-carboxylic acid linked together via the formal condensation of the carboxy groups. It is a secondary metabolite produced by certain strains of bacteria found in the human gut such as Escherichia coli. It has the ability to bind covalently to DNA and is strongly associated with colorectal cancer.
Last Modified13 August 2020
SubmitterMartin Larralde
DownloadsMolfile
FormulaC37H38N8O7S2
Net Charge0
Average Mass770.894
Monoisotopic Mass770.23049
SMILESC[C@H]1CCC(C2=C(CC(=O)NCC(=O)c3csc(C(=O)C(=O)c4csc(CNC(=O)CC5=C(C6=N[C@@H](C)CC6)C(=O)NC56CC6)n4)n3)C3(CC3)NC2=O)=N1
InChIInChI=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
InChIKeyZWKHDAZPVITMAI-ROUUACIJSA-N
Species of MetaboliteComponentSourceComments
Escherichia coli (ncbitaxon:562) - PubMed (29642622)
Klebsiella pneumoniae (ncbitaxon:573) - PubMed (28409125) Strain: K1 CC23
Roles Classification
Biological Roles:
genotoxin  A role played by a chemical compound to induce direct or indirect DNA damage. Such damage can potentially lead to the formation of a malignant tumour, but DNA damage does not lead inevitably to the creation of cancerous cells.
alkylating agent  Highly reactive chemical that introduces alkyl radicals into biologically active molecules and thereby prevents their proper functioning. It could be used as an antineoplastic agent, but it might be very toxic, with carcinogenic, mutagenic, teratogenic, and immunosuppressant actions. It could also be used as a component of poison gases.
carcinogenic agent  A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.
Escherichia coli metabolite  Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
ChEBI Ontology
Outgoing Relation(s)
colibactin (CHEBI:156303) has role Escherichia coli metabolite (CHEBI:76971)
colibactin (CHEBI:156303) has role alkylating agent (CHEBI:22333)
colibactin (CHEBI:156303) has role carcinogenic agent (CHEBI:50903)
colibactin (CHEBI:156303) has role genotoxin (CHEBI:50902)
colibactin (CHEBI:156303) is a 1,3-thiazoles (CHEBI:38418)
colibactin (CHEBI:156303) is a azaspiro compound (CHEBI:35624)
colibactin (CHEBI:156303) is a polyketide (CHEBI:26188)
colibactin (CHEBI:156303) is a pyrroline (CHEBI:23763)
colibactin (CHEBI:156303) is a secondary carboxamide (CHEBI:140325)
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-[{4-[(2-{6-[(2S)-2-methyl-3,4-dihydro-2H-pyrrol-5-yl]-5-oxo-4-azaspiro[2.4]hept-6-en-7-yl}acetamido)acetyl]-1,3-thiazol-2-yl}(oxo)acetyl]-1,3-thiazol-2-yl}methyl)acetamide
Manual XrefsDatabases
CPD-22719MetaCyc
Citations