CHEBI:140152 - cyclosporin A metabolite M1

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ChEBI Name cyclosporin A metabolite M1
ChEBI ID CHEBI:140152
Definition A cyclosporin A derivative that is cyclosporin A in which residue 9 (N-methylleucine) has undergone oxidation so a to introduce a hydroxy group at the carbon bearing the two methyl groups.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C62H111N11O13
Net Charge 0
Average Mass 1218.613
Monoisotopic Mass 1217.83628
InChI InChI=1S/C62H111N11O13/c1-25-27-28-39(13)51(75)50-55(79)65-42(26-2)57(81)67(18)33-47(74)68(19)43(29-34(3)4)54(78)66-48(37(9)10)60(84)69(20)44(30-35(5)6)53(77)63-40(14)52(76)64-41(15)56(80)71(22)46(32-62(16,17)86)59(83)70(21)45(31-36(7)8)58(82)72(23)49(38(11)12)61(85)73(50)24/h25,27,34-46,48-51,75,86H,26,28-33H2,1-24H3,(H,63,77)(H,64,76)(H,65,79)(H,66,78)/b27-25+/t39-,40+,41-,42+,43+,44+,45+,46+,48+,49+,50+,51-/m1/s1
InChIKey ODPRYBDBGFBROY-ANCDGSCPSA-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(O)(C)C)=O)CC(C)C)=O)C)C(C)C)=O)C)[C@@H]([C@@H](C/C=C/C)C)O
Metabolite of Species Details
Homo sapiens (NCBI:txid960) Found in bile (UBERON:0001970). See: PubMed
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 M1 (CHEBI:140152) has role drug metabolite (CHEBI:49103)
cyclosporin A metabolite M1 (CHEBI:140152) is a cyclosporin A derivative (CHEBI:140151)
cyclosporin A metabolite M1 (CHEBI:140152) is a tertiary alcohol (CHEBI:26878)
Incoming cyclosporin A metabolite M10 (CHEBI:140167) has functional parent cyclosporin A metabolite M1 (CHEBI:140152)
cyclosporin A metabolite M13 (CHEBI:140166) has functional parent cyclosporin A metabolite M1 (CHEBI:140152)
cyclosporin A metabolite M16 (CHEBI:140163) has functional parent cyclosporin A metabolite M1 (CHEBI:140152)
cyclosporin A metabolite M8 (CHEBI:140158) has functional parent cyclosporin A metabolite M1 (CHEBI:140152)
IUPAC Name
(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(1R,2R,4E)-1-hydroxy-2-methylhex-4-en-1-yl]-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 Sources
(3S,6S,9S,12R,15S,18S,21S,24S,30S)-30-ethyl-33-((E,1R,2R)-1-hydroxy-2-methyl-hex-4-enyl)-9-(2-hydroxy-2-methyl-propyl)-1,4,7,10,12,15,19,25,28-nonamethyl-6,18,24-tris(2-methylpropyl)-3,21-dipropan-2-yl-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone ChemIDplus
(4-hydroxy-N-methyl-L-leucine)cyclosporine ChemIDplus
(γ-OH)MeLeu-9-cyclosporin ChEBI
(γ-OH)MeLeu-9-cyclosporine ChEBI
AM9
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
cyclosporin metabolite AM9 ChEBI
cyclosporine metabolite AM9 ChEBI
cyclosporine metabolite M1 ChEBI
M1 ChEBI
Registry Number Type Source
89270-25-7 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
1738941 PubMed citation Europe PMC
1943052 PubMed citation Europe PMC
22210099 PubMed citation Europe PMC
2389436 PubMed citation Europe PMC
2642763 PubMed citation Europe PMC
27496445 PubMed citation Europe PMC
2948307 PubMed citation Europe PMC
7914868 PubMed citation Europe PMC
8349948 PubMed citation Europe PMC
8400080 PubMed citation Europe PMC
8894806 PubMed citation Europe PMC
9180163 PubMed citation Europe PMC
Last Modified
16 February 2018