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CHEBI:140158 - cyclosporin A metabolite M8

ChEBI IDCHEBI:140158
ChEBI Namecyclosporin A metabolite M8
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, and in which residue 9 (N-methylleucine) has undergone oxidation so as to introduce a hydroxy group at the carbon bearing the two methyl groups.
Last Modified18 February 2018
SubmitterGareth Owen
DownloadsMolfile
FormulaC62H111N11O14
Net Charge0
Average Mass1234.633
Monoisotopic Mass1233.83120
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)O)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/C62H111N11O14/c1-24-42-57(82)67(17)33-47(75)68(18)43(29-34(2)3)54(79)66-48(37(8)9)60(85)69(19)44(30-35(4)5)53(78)63-40(13)52(77)64-41(14)56(81)71(21)46(32-62(15,16)87)59(84)70(20)45(31-36(6)7)58(83)72(22)49(38(10)11)61(86)73(23)50(55(80)65-42)51(76)39(12)27-25-26-28-74/h25-26,34-46,48-51,74,76,87H,24,27-33H2,1-23H3,(H,63,78)(H,64,77)(H,65,80)(H,66,79)/b26-25+/t39-,40+,41-,42+,43+,44+,45+,46+,48+,49+,50+,51-/m1/s1
InChIKeyOQLOXFAEYPRXJG-DQCBHWIGSA-N
Species of MetaboliteComponentSourceComments
Homo sapiens (ncbitaxon:960)
bile (UBERON:0001970) PubMed (2568911)
bile (UBERON:0001970) PubMed (3538573)
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 M8 (CHEBI:140158) has functional parent cyclosporin A metabolite M1 (CHEBI:140152)
cyclosporin A metabolite M8 (CHEBI:140158) has functional parent cyclosporin A metabolite M17 (CHEBI:140154)
cyclosporin A metabolite M8 (CHEBI:140158) has role drug metabolite (CHEBI:49103)
cyclosporin A metabolite M8 (CHEBI:140158) is a cyclosporin A derivative (CHEBI:140151)
cyclosporin A metabolite M8 (CHEBI:140158) is a primary allylic alcohol (CHEBI:134394)
cyclosporin A metabolite M8 (CHEBI:140158) is a tertiary alcohol (CHEBI:26878)
Incoming Relation(s)
cyclosporin A metabolite M26 (CHEBI:140177) has functional parent cyclosporin A metabolite M8 (CHEBI:140158)
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-9-(2-hydroxy-2-methylpropyl)-6,18,24-triisobutyl-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
cyclosporin A metabolite AM19ChEBI
AM19ChEBI
M8ChEBI
cyclosporin metabolite AM19ChEBI
cyclosporin metabolite M8ChEBI
Citations