CHEBI:48336 - (2R,4S)-ketoconazole

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ChEBI Name (2R,4S)-ketoconazole
ChEBI ID CHEBI:48336
ChEBI ASCII Name (2R,4S)-ketoconazole
Definition A cis-1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine which dioxolane moiety has (2R,4S)-configuration.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C26H28Cl2N4O4
Net Charge 0
Average Mass 531.43100
Monoisotopic Mass 530.149
InChI InChI=1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m0/s1
InChIKey XMAYWYJOQHXEEK-OZXSUGGESA-N
SMILES CC(=O)N1CCN(CC1)c1ccc(OC[C@H]2CO[C@@](Cn3ccnc3)(O2)c2ccc(Cl)cc2Cl)cc1
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
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ChEBI Ontology
Outgoing (2R,4S)-ketoconazole (CHEBI:48336) is a cis-1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine (CHEBI:86411)
(2R,4S)-ketoconazole (CHEBI:48336) is enantiomer of (2S,4R)-ketoconazole (CHEBI:47518)
Incoming ketoconazole (CHEBI:47519) has part (2R,4S)-ketoconazole (CHEBI:48336)
(2S,4R)-ketoconazole (CHEBI:47518) is enantiomer of (2R,4S)-ketoconazole (CHEBI:48336)
IUPAC Name
1-acetyl-4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine
Synonym Source
(2R,4S)-1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine ChEBI
Manual Xrefs Databases
KKK PDBeChem
LSM-5430 LINCS
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Registry Numbers Types Sources
4241048 Reaxys Registry Number Reaxys
4241048 Beilstein Registry Number Beilstein
Last Modified
25 February 2016
General Comment
2015-07-10 There is a separate entry for the antifungal drug ketoconazole, which is a racemate comprising equimolar amounts of (2R,4S)- and (2S,4R)-ketoconazole.