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CHEBI:75276 - ikarugamycin

ChEBI IDCHEBI:75276
ChEBI Nameikarugamycin
Stars
DefinitionA polyketide macrolactam containing a tetramic acid (pyrrolidine-2,4-dione) ring system. It is isolated from Streptomyces as an antibiotic with antiprotozoal and cytotoxic activities.
Last Modified29 July 2024
Submitternamrata
DownloadsMolfile
FormulaC29H38N2O4
Net Charge0
Average Mass478.633
Monoisotopic Mass478.28316
SMILES[H][C@]12C=C[C@@]3([H])[C@H](CC)[C@H](C)C[C@]3([H])[C@@]1([H])C[C@@]1([H])/C=C/C(=O)C3=C(O)[C@]([H])(CCCNC(=O)/C=C\C[C@]21[H])NC3=O
InChIInChI=1S/C29H38N2O4/c1-3-18-16(2)14-22-20(18)10-11-21-19-6-4-8-26(33)30-13-5-7-24-28(34)27(29(35)31-24)25(32)12-9-17(19)15-23(21)22/h4,8-12,16-24,34H,3,5-7,13-15H2,1-2H3,(H,30,33)(H,31,35)/b8-4-,12-9+/t16-,17-,18-,19+,20+,21-,22+,23+,24+/m1/s1
InChIKeyWSUGGLXIPUHOSG-QOMLVTEJSA-N
Species of MetaboliteComponentSourceComments
Streptomyces phaeochromogenes (ncbitaxon:1923) - PubMed (4625358) Strain: var. ikaruganensis
Streptomyces sp. MDG-04-17-069 (ncbitaxon:698778) cell suspension culture (BTO:0000221) PubMed (19968258)
Roles Classification
Biological Roles:
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
antiprotozoal drug  Any antimicrobial drug which is used to treat or prevent protozoal infections.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Applications:
antiprotozoal drug  Any antimicrobial drug which is used to treat or prevent protozoal infections.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
ikarugamycin (CHEBI:75276) has role antimicrobial agent (CHEBI:33281)
ikarugamycin (CHEBI:75276) has role antineoplastic agent (CHEBI:35610)
ikarugamycin (CHEBI:75276) has role antiprotozoal drug (CHEBI:35820)
ikarugamycin (CHEBI:75276) has role apoptosis inducer (CHEBI:68495)
ikarugamycin (CHEBI:75276) has role bacterial metabolite (CHEBI:76969)
ikarugamycin (CHEBI:75276) is a azamacrocycle (CHEBI:52898)
ikarugamycin (CHEBI:75276) is a enone (CHEBI:51689)
ikarugamycin (CHEBI:75276) is a lactam (CHEBI:24995)
ikarugamycin (CHEBI:75276) is a organic heteropentacyclic compound (CHEBI:38164)
ikarugamycin (CHEBI:75276) is a polyketide (CHEBI:26188)
Incoming Relation(s)
butremycin (CHEBI:152570) has functional parent ikarugamycin (CHEBI:75276)
IUPAC Name 
(2R,3R,3aS,5aR,5bS,7Z,14S,19E,20aS,21aR,21bR)-3-ethyl-22-hydroxy-2-methyl-2,3,3a,5a,5b,6,10,11,12,13,14,15,20a,21,21a,21b-hexadecahydro-1H-14,17-(metheno)-as-indaceno[3,2-k][1,6]diazacycloheptadecine-9,16,18(17H)-trione
Manual XrefsDatabases
GB2120098Patent
C00018842KNApSAcK
Registry NumbersSources
Reaxys:771794Reaxys
CAS:36531-78-9ChemIDplus
Citations