CHEBI:75276 - ikarugamycin

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ChEBI Name ikarugamycin
ChEBI ID CHEBI:75276
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C29H38N2O4
Net Charge 0
Average Mass 478.633
Monoisotopic Mass 478.28316
InChI InChI=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
InChIKey WSUGGLXIPUHOSG-QOMLVTEJSA-N
SMILES C1=C[C@@]2([C@@]([C@@]3([C@]1([C@@]4([C@](C3)([H])C=CC(C=5C(=O)N[C@@](CCCNC(C=CC4)=O)(C5O)[H])=O)[H])[H])[H])(C[C@H]([C@H]2CC)C)[H])[H]
Metabolite of Species Details
Streptomyces phaeochromogenes (NCBI:txid1923) of strain var. ikaruganensis See: PubMed
Streptomyces sp. MDG-04-17-069 (NCBI:txid698778) Found in cell suspension culture (BTO:0000221). See: PubMed
Roles Classification
Biological Role(s): antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
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.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
Application(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 Xrefs Databases
C00018842 KNApSAcK
GB2120098 Patent
View more database links
Registry Numbers Types Sources
329868 Beilstein Registry Number Alan Wood's Pesticides
36531-78-9 CAS Registry Number ChemIDplus
771794 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11160755 PubMed citation Europe PMC
1572375 PubMed citation Europe PMC
21392513 PubMed citation Europe PMC
23584286 PubMed citation Europe PMC
24706593 PubMed citation Europe PMC
25711294 PubMed citation Europe PMC
28128495 PubMed citation Europe PMC
31944405 PubMed citation Europe PMC
32021101 PubMed citation Europe PMC
4625358 PubMed citation Europe PMC
Last Modified
03 June 2020