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CHEBI:140154 - cyclosporin A metabolite M17

Default Structure
ChEBI IDCHEBI:140154
ChEBI Namecyclosporin A metabolite M17
Stars
DefinitionA 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.
Last Modified18 February 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC62H111N11O13
Net Charge0
Average Mass1218.634
Monoisotopic Mass1217.83628
SMILESCC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C/C=C/CO)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O
InChIInChI=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
InChIKeyZPZHKIOMBYYVRD-WRDPQARASA-N
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:960) bile (UBERON:0001970) PubMed (2568911)
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
6-[(2S,3R,4R,6E)-3,8-dihydroxy-4-methyl-2-(methylamino)-6-octenoic acid]cyclosporinChEBI
AM1ChEBI
CsA M17ChemIDplus
cyclosporine A metabolite M17ChEBI
cyclosporine metabolite M17ChemIDplus
cyclosporin metabolite AM1ChEBI
Registry NumbersSources
CAS:89270-28-0ChemIDplus
Citations