SETILEUTON

ID: ALA2105653

Chembl Id: CHEMBL2105653

Cas Number: 910656-27-8

PubChem CID: 11856170

Max Phase: Phase

Molecular Formula: C22H17F4N3O4

Molecular Weight: 463.39

Molecule Type: Small molecule

Names and Identifiers

Synonyms: MK-0633 | SETILEUTON|910656-27-8|MK-0633|0U2750935P|4-(4-fluorophenyl)-7-[[[5-[(2S)-1,1,1-trifluoro-2-hydroxybutan-2-yl]-1,3,4-oxadiazol-2-yl]amino]methyl]chromen-2-one|(S)-4-(4-fluorophenyl)-7-(((5-(1,1,1-trifluoro-2-hydroxybutan-2-yl)-1,3,4-oxadiazol-2-yl)amino)methyl)-2H-chromen-2-one|2H-1-Benzopyran-2-one, 4-(4-fluorophenyl)-7-(((5-((1S)-1-hydroxy-1-(trifluoromethyl)propyl)-1,3,4-oxadiazol-2-yl)amino)methyl)-|Setileuton [USAN]|Setileuton [USAN:INN]|UNII-0U2750935P|MK0633|MK 0633|SETILEUTON [Show More⌵

Canonical SMILES:  CC[C@](O)(c1nnc(NCc2ccc3c(-c4ccc(F)cc4)cc(=O)oc3c2)o1)C(F)(F)F

Standard InChI:  InChI=1S/C22H17F4N3O4/c1-2-21(31,22(24,25)26)19-28-29-20(33-19)27-11-12-3-8-15-16(10-18(30)32-17(15)9-12)13-4-6-14(23)7-5-13/h3-10,31H,2,11H2,1H3,(H,27,29)/t21-/m0/s1

Standard InChI Key:  MAOIDRRXRLYJNV-NRFANRHFSA-N

Alternative Forms

1. Parent:

   

   ALA2105653

   SETILEUTON

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 463.39

Molecular Weight (Monoisotopic): 463.1155

AlogP: 4.75

#Rotatable Bonds: 6

Polar Surface Area: 101.39

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.91

CX Basic pKa:

CX LogP: 3.65

CX LogD: 3.64

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.31

Np Likeness Score: -0.79

References

1. USP Dictionary of USAN and International Names (2010 edition) and USAN registrations 2007-date, 

2. Maciolek CM, Ma B, Menzel K, Laliberte S, Bateman K, Krolikowski P, Gibson CR..  (2011)  Novel cytochrome P450-mediated ring opening of the 1,3,4-oxadiazole in setileuton, a 5-lipoxygenase inhibitor.,  39  (5): [PMID:21325431] [10.1124/dmd.110.037366]

3. Bruno F, Spaziano G, Liparulo A, Roviezzo F, Nabavi SM, Sureda A, Filosa R, D'Agostino B..  (2018)  Recent advances in the search for novel 5-lipoxygenase inhibitors for the treatment of asthma.,  153  [PMID:29133059] [10.1016/j.ejmech.2017.10.020]

Source

Source(2):

• Scientific Literature
• USP Dictionary of USAN and International Drug Names