CHEBI:599440 - amorolfine

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ChEBI Name amorolfine
ChEBI ID CHEBI:599440
Definition A member of the class of morpholines that is cis-2,6-dimethylmorpholine in which the hydrogen attached to the nitrogen is replaced by a racemic 2-methyl-3-[p-(2-methylbutan-2-yl)phenyl]propyl group. An inhibitor of the action of squalene monooxygenase, Δ14 reductase and D7-D8 isomerase and an antifungal agent, it is used (generally as its hydrochloride salt) for the topical treatment of fungal nail and skin infections.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:31779
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Formula C21H35NO
Net Charge 0
Average Mass 317.50870
Monoisotopic Mass 317.272
InChI InChI=1S/C21H35NO/c1-7-21(5,6)20-10-8-19(9-11-20)12-16(2)13-22-14-17(3)23-18(4)15-22/h8-11,16-18H,7,12-15H2,1-6H3/t16?,17-,18+
InChIKey MQHLMHIZUIDKOO-AYHJJNSGSA-N
SMILES CCC(C)(C)c1ccc(CC(C)CN2C[C@H](C)O[C@H](C)C2)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 )
Biological Role(s): EC 1.14.13.132 (squalene monooxygenase) inhibitor
An EC 1.14.13.* (oxidoreductase acting on paired donors, incorporating 1 atom of oxygen, with NADH or NADPH as one donor) inhibitor that interferes with the action of squalene monooxygenase (EC 1.14.13.132).
EC 5.3.3.5 (cholestenol Delta-isomerase) inhibitor
An EC 5.3.3.* (intramolecular oxidase transposing C2C bonds) inhibitor that interferes with the action of a cholestenol Delta-isomerase (EC 5.3.3.5).
EC 1.3.1.70 (Delta(14)-sterol reductase) inhibitor
An EC 1.3.1.* (oxidoreductase acting on donor CH-CH group, NAD+ or NADP+ as acceptor) inhibitor that interferes with the action of Delta14-sterol reductase (EC 1.3.1.70.
antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via morpholine antifungal drug )
antifungal agent
An antimicrobial agent that destroys fungi by suppressing their ability to grow or reproduce.
(via morpholine antifungal agent )
Application(s): antifungal drug
Any antifungal agent used to prevent or treat fungal infections in humans or animals.
(via morpholine antifungal drug )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing amorolfine (CHEBI:599440) has role EC 1.14.13.132 (squalene monooxygenase) inhibitor (CHEBI:59285)
amorolfine (CHEBI:599440) has role EC 1.3.1.70 (Δ14-sterol reductase) inhibitor (CHEBI:83319)
amorolfine (CHEBI:599440) has role EC 5.3.3.5 (cholestenol Δ-isomerase) inhibitor (CHEBI:86385)
amorolfine (CHEBI:599440) is a morpholine antifungal drug (CHEBI:87135)
amorolfine (CHEBI:599440) is a tertiary amino compound (CHEBI:50996)
amorolfine (CHEBI:599440) is conjugate acid of amorolfine(1+) (CHEBI:86380)
Incoming amorolfine(1+) (CHEBI:86380) is conjugate base of amorolfine (CHEBI:599440)
IUPAC Name
(2R,6S)-2,6-dimethyl-4-{2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl}morpholine
INNs Sources
amorolfina ChemIDplus
amorolfine KEGG DRUG
amorolfinum ChemIDplus
Synonyms Sources
(±)-cis-2,6-dimethyl-4-(2-methyl-3-(p-tert-pentylphenyl)propyl)morpholine ChemIDplus
meso-2,6-dimethyl-4-(2-methyl-3-(p-tert-pentylphenyl)propyl)morpholine ChEBI
meso-2,6-dimethyl-4-{2-methyl-3-[4-(2-methylbutan-2-yl)phenyl]propyl}morpholine ChEBI
Manual Xrefs Databases
188 DrugCentral
Amorolfine Wikipedia
D01720 KEGG DRUG
D02923 KEGG DRUG
View more database links
Registry Numbers Types Sources
78613-35-1 CAS Registry Number KEGG DRUG
78613-35-1 CAS Registry Number ChemIDplus
8154195 Beilstein Registry Number Beilstein
Citation Waiting for Citations Type Source
17620378 PubMed citation ChEMBL
Last Modified
22 February 2017