Ikarugamycin
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Ikarugamycin
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CAS No:
36531-78-9
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Formula:
C29H38N2O4
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Chemical Name:
Ikarugamycin
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Synonyms:
14,17-Metheno-17H-as-indaceno[3,2-k][1,6]diazacycloheptadecine-9,16,18(1H)-trione,3-ethyl-2,3,3a,5a,5b,6,10,11,12,13,14,15,20a,21,21a,21b-hexadecahydro-22-hydroxy-2-methyl-,(2R,3R,3aS,5aR,5bS,7Z,14S,19E,20aS,21aR,21bR)-;Ikarugamycin;14,17-Metheno-17H-as-indaceno[3,2-k][1,6]diazacycloheptadecine,ikarugamycin deriv.;(2R,3R,3aS,5aR,5bS,7Z,14S,19E,20aS,21aR,21bR)-3-Ethyl-2,3,3a,5a,5b,6,10,11,12,13,14,15,20a,21,21a,21b-hexadecahydro-22-hydroxy-2-methyl-14,17-metheno-17H-as-indaceno[3,2-k][1,6]diazacycloheptadecine-9,16,18(1H)-trione;14,17-Metheno-17H-as-indaceno[3,2-k][1,6]diazacycloheptadecine-9,16,18(1H)-trione,3-ethyl-2,3,3a,5a,5b,6,10,11,12,13,14,15,20a,21,21a,21b-hexadecahydro-22-hydroxy-2-methyl-,[2R-(2R*,3R*,3aS*,5aR*,5bS*,14S*,20aS*,21aR*,21bR*)]-;[2R-(2R*,3R*,3aS*,5aR*,5bS*,14S*,20aS*,21aR*,21bR*)]-3-Ethyl-2,3,3a,5a,5b,6,10,11,12,13,14,15,20a,21,21a,21b-hexadecahydro-22-hydroxy-2-methyl-14,17-metheno-17H-as-indaceno[3,2-k][1,6]diazacycloheptadecine-9,16,18(1H)-trione;SML 0188;11091-37-5
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CAS No:
Description
Ikarugamycin is 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. It has a role as an antimicrobial agent, an antiprotozoal drug, an antineoplastic agent, an apoptosis inducer and a bacterial metabolite. It is a lactam, an azamacrocycle, an enone, a polyketide and an organic heteropentacyclic compound.
Ikarugamycin Use and Manufacturing
Ikarugamycin is an unusual pentacyclic tetramic acid produced by Streptomyces phaeochromogenes, with potent activity against the protozoan, Trichomonas vaginalis, reported in 1972. Ikarugamycin also demonstrates selective Gram positive antibacterial activity, and anti-ucler activity possibly via inhibition of H. pylori. In addition, ikarugamycin inhibits the uptake of oxidized low-density lipoprotein in mouse macrophages, blocks PMA and Nef-mediated cell surface CD4 down-regulation, and inhibits clathrin-coated pit-mediated endocytosis. Importantly, ikarugamycin is emerging as a useful agent for studying the process of endocytosis.
Computed Properties
Molecular Weight:478.6
XLogP3:5
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:478.28315770
Monoisotopic Mass:478.28315770
Topological Polar Surface Area:95.5
Heavy Atom Count:35
Complexity:1010
Defined Atom Stereocenter Count:9
Defined Bond Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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