Term: | cyclosporin A metabolite M17 |
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Accession: | CHEBI:140154
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Definition: | A cyclosporin A derivative that is cyclosporin A in which residue 1 [(2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)oct-6-enoic acid] has undergone allylic oxidation to give the corresponding primary allylic alcohol. It specifically inhibits growth of renal cells in culture. |
Synonyms: | exact_synonym: | (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-33-[(1R,2R,4E)-1,6-dihydroxy-2-methylhex-4-en-1-yl]-30-ethyl-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone |
| related_synonym: | 6-[(2S,3R,4R,6E)-3,8-dihydroxy-4-methyl-2-(methylamino)-6-octenoic acid]cyclosporin; AM1; CsA M17; Formula=C62H111N11O13; InChI=1S/C62H111N11O13/c1-24-43-58(82)67(17)33-48(75)68(18)44(29-34(2)3)55(79)66-49(38(10)11)61(85)69(19)45(30-35(4)5)54(78)63-41(15)53(77)64-42(16)57(81)70(20)46(31-36(6)7)59(83)71(21)47(32-37(8)9)60(84)72(22)50(39(12)13)62(86)73(23)51(56(80)65-43)52(76)40(14)27-25-26-28-74/h25-26,34-47,49-52,74,76H,24,27-33H2,1-23H3,(H,63,78)(H,64,77)(H,65,80)(H,66,79)/b26-25+/t40-,41+,42-,43+,44+,45+,46+,47+,49+,50+,51+,52-/m1/s1; InChIKey=ZPZHKIOMBYYVRD-WRDPQARASA-N; M17; OL-17; SMILES=[C@H]1(N(C([C@@H](N(C([C@@H](N(C)C([C@@H](N(C([C@H](NC([C@@H](NC([C@@H](N(C([C@@H](NC([C@@H](N(C)C(CN(C([C@@H](NC1=O)CC)=O)C)=O)CC(C)C)=O)C(C)C)=O)C)CC(C)C)=O)C)=O)C)=O)C)CC(C)C)=O)CC(C)C)=O)C)C(C)C)=O)C)[C@@H]([C@@H](C/C=C/CO)C)O; cyclosporin metabolite AM1; cyclosporin metabolite M17; cyclosporine A metabolite M17; cyclosporine metabolite M17 |
| xref: | CAS:89270-28-0; PMID:17908922; PMID:1834063; PMID:1943052; PMID:2389436; PMID:2642763; PMID:2784905; PMID:2948307; PMID:2950629; PMID:7914868; PMID:8234147; PMID:8349948; PMID:8400080; PMID:8894806; PMID:8971957; PMID:9106068; PMID:9180163; PMID:9555934 |
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