CHEBI:140154 - cyclosporin A metabolite M17

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ChEBI Name cyclosporin A metabolite M17 ChEBI ID CHEBI:140154 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. Stars This entity has been manually annotated by the ChEBI Team. Supplier Information Download Molfile XML SDF Find compounds which contain this structure Find compounds which resemble this structure Take structure to the Advanced Search Formula C62H111N11O13 Net Charge 0 Average Mass 1218.613 Monoisotopic Mass 1217.83628 InChI 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 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 Metabolite of Species Details Homo sapiens (NCBI:txid960) Found in bile (UBERON:0001970). See: PubMed Roles Classification Chemical Role(s): Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Biological Role(s): drug metabolite View more via ChEBI Ontology ChEBI Ontology Outgoing cyclosporin A metabolite M17 (CHEBI:140154) has role drug metabolite (CHEBI:49103) cyclosporin A metabolite M17 (CHEBI:140154) is a cyclosporin A derivative (CHEBI:140151) cyclosporin A metabolite M17 (CHEBI:140154) is a primary allylic alcohol (CHEBI:134394) Incoming cyclosporin A metabolite M18 (CHEBI:140175) has functional parent cyclosporin A metabolite M17 (CHEBI:140154) cyclosporin A metabolite M1A (CHEBI:140178) has functional parent cyclosporin A metabolite M17 (CHEBI:140154) cyclosporin A metabolite M25 (CHEBI:140172) has functional parent cyclosporin A metabolite M17 (CHEBI:140154) cyclosporin A metabolite M8 (CHEBI:140158) has functional parent cyclosporin A metabolite M17 (CHEBI:140154) IUPAC Name (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 Synonyms Sources 6-[(2S,3R,4R,6E)-3,8-dihydroxy-4-methyl-2-(methylamino)-6-octenoic acid]cyclosporin ChEBI AM1 Note: (2018-02-14) The letter A before the letter M indicates that the compound is a metabolite of cyclosporin A; G would mean it was a metabolite of cyclosporin G, etc. (see Transplant. Proc., 1990, 22/3, 1357). ChEBI CsA M17 ChemIDplus cyclosporin metabolite AM1 ChEBI cyclosporin metabolite M17 ChEBI cyclosporine A metabolite M17 ChEBI cyclosporine metabolite M17 ChemIDplus M17 ChEBI OL 17 ChEBI OL-17 ChEBI Registry Number Type Source 89270-28-0 CAS Registry Number ChemIDplus Citations Types Sources 17908922 PubMed citation Europe PMC 1834063 PubMed citation Europe PMC 1943052 PubMed citation Europe PMC 2389436 PubMed citation Europe PMC 2642763 PubMed citation Europe PMC 2784905 PubMed citation Europe PMC 2948307 PubMed citation Europe PMC 2950629 PubMed citation Europe PMC 7914868 PubMed citation Europe PMC 8234147 PubMed citation Europe PMC 8349948 PubMed citation Europe PMC 8400080 PubMed citation Europe PMC 8894806 PubMed citation Europe PMC 8971957 PubMed citation Europe PMC 9106068 PubMed citation Europe PMC 9180163 PubMed citation Europe PMC 9555934 PubMed citation Europe PMC Last Modified 18 February 2018