CHEBI:156303 - colibactin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name colibactin
ChEBI ID CHEBI:156303
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Martin Larralde
Supplier Information
Download Molfile XML SDF
Formula C37H38N8O7S2
Net Charge 0
Average Mass 770.880
Monoisotopic Mass 770.23049
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
InChIKey ZWKHDAZPVITMAI-ROUUACIJSA-N
SMILES C[C@H]1CCC(=N1)C1=C(CC(=O)NCC(=O)C2=CSC(=N2)C(=O)C(=O)C2=CSC(CNC(=O)CC3=C(C(=O)NC33CC3)C3=N[C@@H](C)CC3)=N2)C2(CC2)NC1=O
Metabolite of Species Details
Escherichia coli (NCBI:txid562) See: PubMed
Klebsiella pneumoniae (NCBI:txid573) of strain K1 CC23 See: PubMed
Roles Classification
Biological Role(s): 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.
Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
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.
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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 Xref Database
CPD-22719 MetaCyc
View more database links
Citations Waiting for Citations Types Sources
17224306 PubMed citation Europe PMC
29642622 PubMed citation SUBMITTER
30765538 PubMed citation Europe PMC
31395743 PubMed citation SUBMITTER
31527851 PubMed citation Europe PMC
31541229 PubMed citation Europe PMC
31578245 PubMed citation Europe PMC
31977191 PubMed citation Europe PMC
32037530 PubMed citation Europe PMC
32169880 PubMed citation Europe PMC
32175032 PubMed citation Europe PMC
32317778 PubMed citation Europe PMC
32475872 PubMed citation Europe PMC
32483361 PubMed citation Europe PMC
32507544 PubMed citation Europe PMC
32527463 PubMed citation Europe PMC
32611705 PubMed citation Europe PMC
32661091 PubMed citation Europe PMC
32669458 PubMed citation Europe PMC
32727866 PubMed citation Europe PMC
32767847 PubMed citation Europe PMC
Last Modified
13 August 2020