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CHEBI:156322 - luminmycin A

ChEBI IDCHEBI:156322
ChEBI Nameluminmycin A
Stars
DefinitionA syrbactin derivative with a 12-carbon sidechain. It exhibits a protease-inhibition activity, and is synthesized by a non-ribosomal peptide synthase in Photorhabdus luminescens.
SubmitterMartin Larralde
DownloadsMolfile
FormulaC27H44N4O5
Net Charge0
Average Mass504.672
Monoisotopic Mass504.33117
SMILES[H]C1=C(\[H])[C@]([H])(C)/N=C(/O)[C@@]([H])(/N=C(\O)[C@@]([H])(/N=C(O)/C([H])=C([H])/C([H])=C(\[H])CCCCCCC)[C@@]([H])(C)O)CCCC/N=C\1O
InChIInChI=1S/C27H44N4O5/c1-4-5-6-7-8-9-10-11-12-16-24(34)31-25(21(3)32)27(36)30-22-15-13-14-19-28-23(33)18-17-20(2)29-26(22)35/h10-12,16-18,20-22,25,32H,4-9,13-15,19H2,1-3H3,(H,28,33)(H,29,35)(H,30,36)(H,31,34)/b11-10+,16-12+,18-17-/t20-,21+,22-,25-/m0/s1
InChIKeyCXVPCSSIDACGGV-KNTXCBEDSA-N
Species of MetaboliteComponentSourceComments
Photorhabdus laumondii subsp. laumondii TTO1 (ncbitaxon:243265) - PubMed (22909174)
Photorhabdus asymbiotica subsp. asymbiotica ATCC 43949 (ncbitaxon:553480) - PubMed (23095088)
unclassified Burkholderia (ncbitaxon:2613784) - PubMed (25147087) Strain: DSM7029
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
Application:
proteasome inhibitor  A drug that blocks the action of proteasomes, cellular complexes that break down proteins.
ChEBI Ontology
Outgoing Relation(s)
luminmycin A (CHEBI:156322) has functional parent syrbactin (CHEBI:82671)
luminmycin A (CHEBI:156322) has role bacterial metabolite (CHEBI:76969)
luminmycin A (CHEBI:156322) has role proteasome inhibitor (CHEBI:52726)
luminmycin A (CHEBI:156322) is a azamacrocycle (CHEBI:52898)
luminmycin A (CHEBI:156322) is a homodetic cyclic peptide (CHEBI:24613)
luminmycin A (CHEBI:156322) is a lactam (CHEBI:24995)
luminmycin A (CHEBI:156322) is a pentol (CHEBI:37205)
luminmycin A (CHEBI:156322) is a polyketide (CHEBI:26188)
IUPAC Name 
(2E,4E)-N-[(2S,3R)-3-Hydroxy-1-{[(3E,5S,8S)-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl]amino}-1-oxo-2-butanyl]-2,4-dodecadienamide
Citations