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CHEBI:75276 - ikarugamycin

Default Structure
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:
antimicrobial agent  A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antiprotozoal drug  Any antimicrobial drug which is used to treat or prevent protozoal infections.
apoptosis inducer  Any substance that induces the process of apoptosis (programmed cell death) in multi-celled organisms.
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
C00018842KNApSAcK
GB2120098Patent
Registry NumbersSources
Reaxys:771794Reaxys
CAS:36531-78-9ChemIDplus
Citations