CHEBI:66360 - vinylamycin

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name vinylamycin
ChEBI ID CHEBI:66360
Definition A 15-membered cyclodepsipeptide isolated from Streptomyces sp.M1982-63F1. It exhibits moderate activity against Gram-positive bacteria.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C26H43N3O6
Net Charge 0
Average Mass 493.63610
Monoisotopic Mass 493.31519
InChI InChI=1S/C26H43N3O6/c1-7-8-9-10-11-17(4)23-20(14-15-30)25(33)27-18(5)12-13-21(31)28-19(6)24(32)29-22(16(2)3)26(34)35-23/h12-13,16-17,19-20,22-23,30H,5,7-11,14-15H2,1-4,6H3,(H,27,33)(H,28,31)(H,29,32)/b13-12+/t17?,19-,20?,22+,23?/m0/s1
InChIKey ONGSLGFACDWAIV-OIXFFAKGSA-N
SMILES CCCCCCC(C)C1OC(=O)[C@H](NC(=O)[C@H](C)NC(=O)\C=C\C(=C)NC(=O)C1CCO)C(C)C
Metabolite of Species Details
Streptomyces sp. (NCBI:txid1931) of strain MI982-63F1 See: PubMed
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): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing vinylamycin (CHEBI:66360) has role antibacterial agent (CHEBI:33282)
vinylamycin (CHEBI:66360) has role antimicrobial agent (CHEBI:33281)
vinylamycin (CHEBI:66360) has role metabolite (CHEBI:25212)
vinylamycin (CHEBI:66360) is a cyclodepsipeptide (CHEBI:35213)
vinylamycin (CHEBI:66360) is a macrocycle (CHEBI:51026)
vinylamycin (CHEBI:66360) is a primary alcohol (CHEBI:15734)
IUPAC Name
(3R,6S,9E)-14-(2-hydroxyethyl)-3-isopropyl-6-methyl-11-methylene-15-(octan-2-yl)-1-oxa-4,7,12-triazacyclopentadec-9-ene-2,5,8,13-tetrone
Citations Waiting for Citations Types Sources
10604756 PubMed citation Europe PMC
22591554 PubMed citation Europe PMC
Last Modified
12 October 2012
General Comment
2012-10-12 The structure depicted (see: Carr G. et al, Org. Lett., 2012, 14, 2822) is a revised structure from the one originally proposed by Igarashi M. et al, (J. Antibiot., 1999, 52, 873).