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CHEBI:133127 - lugdunin

ChEBI IDCHEBI:133127
ChEBI Namelugdunin
Stars
DefinitionA thiazolidine-containing homodetic cyclic peptide that is isolated from human nasal bacteria. Exhibits bactericidal activity against many major pathogens including methicillin-resistant Staphylococcus aureus (MRSA).
Last Modified23 August 2016
SubmitterSteve
DownloadsMolfile
FormulaC40H62N8O6S
Net Charge0
Average Mass783.053
Monoisotopic Mass782.45130
SMILESCC(C)C[C@H]1NC(=O)[C@H](Cc2cnc3ccccc23)NC(=O)[C@@H](C(C)C)NC(=O)[C@@H]2CSC(N2)[C@H](C(C)C)NC(=O)[C@@H](C(C)C)NC(=O)[C@H](C(C)C)NC1=O
InChIInChI=1S/C40H62N8O6S/c1-19(2)15-27-35(50)45-31(21(5)6)38(53)47-32(22(7)8)39(54)48-33(23(9)10)40-44-29(18-55-40)36(51)46-30(20(3)4)37(52)43-28(34(49)42-27)16-24-17-41-26-14-12-11-13-25(24)26/h11-14,17,19-23,27-33,40-41,44H,15-16,18H2,1-10H3,(H,42,49)(H,43,52)(H,45,50)(H,46,51)(H,47,53)(H,48,54)/t27-,28+,29+,30-,31+,32-,33+,40?/m1/s1
InChIKeyQZNGYMKAHFFKCJ-ZBQZSICZSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:9606) - PubMed (27466123)
Rattus norvegicus (ncbitaxon:10116) - PubMed (27466123)
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
human metabolite  Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
rat metabolite  Any mammalian metabolite produced during a metabolic reaction in rat (Rattus norvegicus).
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
ChEBI Ontology
Outgoing Relation(s)
lugdunin (CHEBI:133127) has role human metabolite (CHEBI:77746)
lugdunin (CHEBI:133127) has role rat metabolite (CHEBI:86264)
lugdunin (CHEBI:133127) is a homodetic cyclic peptide (CHEBI:24613)
lugdunin (CHEBI:133127) is a indoles (CHEBI:24828)
lugdunin (CHEBI:133127) is a macrocycle (CHEBI:51026)
lugdunin (CHEBI:133127) is a peptide antibiotic (CHEBI:25903)
lugdunin (CHEBI:133127) is a thiazolidines (CHEBI:35622)
IUPAC Name 
(1R,4R,7S,10R,13S,16R,19S)-7-[(1H-indol-3-yl)methyl]-10-(2-methylpropyl)-4,13,16,19-tetra(propan-2-yl)-21-thia-3,6,9,12,15,18,23-heptaazabicyclo[18.2.1]tricosane-2,5,8,11,14,17-hexone
Manual XrefsDatabases
LugduninWikipedia
Citations