CHEBI:142547 - coelimycin P1

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name coelimycin P1
ChEBI ID CHEBI:142547
Definition An organosulfur heterocyclic compound that is 1,5-oxathiocane which has been substituted at the 2-pro-R, 3, 6, and 8 positions by oxo, acetamido, 5,6-dihydropyridin-2(1H)-ylidene, and (2E)-but-2-enoyl groups, respectively, and which has been dehydrogenated to introduce a double bond at the 7-8 position. It was isolated from Streptomyces coelicolor M145 after genetically engineered increase of the metabolic flux and is the product of a polyketide biosynthetic gene cluster.
Stars This entity has been manually annotated by the ChEBI Team.
Submitter Kristian Axelsen
Supplier Information
Download Molfile XML SDF
more structures >>
Formula C17H20N2O4S
Net Charge 0
Average Mass 348.418
Monoisotopic Mass 348.11438
InChI InChI=1S/C17H20N2O4S/c1-3-6-14(21)15-9-16(12-7-4-5-8-18-12)24-10-13(17(22)23-15)19-11(2)20/h3-4,6-7,9,13,18H,5,8,10H2,1-2H3,(H,19,20)/b6-3+,15-9-,16-12+/t13-/m0/s1
InChIKey RHGMVWUZXGSXCT-IAGKGVPHSA-N
SMILES C1S\C(\C=C(OC([C@]1(NC(C)=O)[H])=O)C(/C=C/C)=O)=C/2\NCCC=C2
Metabolite of Species Details
Streptomyces coelicolor (NCBI:txid1902) Streptomyces coelicolor M145 after genetically engineered increase of the metabolic flux of strain M145 See: DOI
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing coelimycin P1 (CHEBI:142547) has parent hydride 1,5-oxathiocane (CHEBI:142569)
coelimycin P1 (CHEBI:142547) has role bacterial metabolite (CHEBI:76969)
coelimycin P1 (CHEBI:142547) is a acetamides (CHEBI:22160)
coelimycin P1 (CHEBI:142547) is a dihydropyridine (CHEBI:50075)
coelimycin P1 (CHEBI:142547) is a enamine (CHEBI:47989)
coelimycin P1 (CHEBI:142547) is a enone (CHEBI:51689)
coelimycin P1 (CHEBI:142547) is a lactone (CHEBI:25000)
coelimycin P1 (CHEBI:142547) is a organosulfur heterocyclic compound (CHEBI:38106)
IUPAC Name
N-[(3R,6E,7Z)-8-[(2E)-but-2-enoyl]-6-(5,6-dihydropyridin-2(1H)-ylidene)-2-oxo-3,4-dihydro-2H,6H-1,5-oxathiocin-3-yl]acetamide
Synonyms Sources
N-[(3R)-8-[(2E)-but-2-enoyl]-2-oxo-6-[(2E)-1,2,5,6-tetrahydropyridin-2-ylidene]-2,3,4,6-tetrahydro-1,5-oxathiocin-3-yl]acetamide SUBMITTER
N-[(3R,6E,7Z)-8-[(E)-but-2-enoyl]-6-(2,3-dihydro-1H-pyridin-6-ylidene)-2-oxo-3,4-dihydro-1,5-oxathiocin-3-yl]acetamide ChEBI
Citations Waiting for Citations Types Sources
17009021 PubMed citation SUBMITTER
26734097 PubMed citation Europe PMC
28451186 PubMed citation Europe PMC
Last Modified
13 November 2018
General Comment
2018-11-13 See also Gomez-Escribano, J. P.; Song, L.; Fox, D. J.; Yeo, V.; Bibb, M. J.;Challis, G. L. (2012) Structure and biosynthesis of the unusual polyketide alkaloid coelimycin P1, a metabolic product of the cpk gene cluster of Streptomyces coelicolor M145. Chem. Sci., v3, 2716-2720. doi:10.1039/c2sc20410j