((2R,5R)-5-((5-fluoropyridin-2-yloxy)methyl)-2-methylpiperidin-1-yl)(5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl)methanone

ID: ALA3235249

Chembl Id: CHEMBL3235249

PubChem CID: 25127493

Max Phase: Preclinical

Molecular Formula: C22H24FN5O2

Molecular Weight: 409.47

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(-n2nccn2)c(C(=O)N2C[C@H](COc3ccc(F)cn3)CC[C@H]2C)c1

Standard InChI:  InChI=1S/C22H24FN5O2/c1-15-3-7-20(28-25-9-10-26-28)19(11-15)22(29)27-13-17(5-4-16(27)2)14-30-21-8-6-18(23)12-24-21/h3,6-12,16-17H,4-5,13-14H2,1-2H3/t16-,17-/m1/s1

Standard InChI Key:  SWJLISCOLSUHGG-IAGOWNOFSA-N

Alternative Forms

1. Parent:

   

   ALA3235249

   [(2R,5R)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone

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: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 409.47

Molecular Weight (Monoisotopic): 409.1914

AlogP: 3.43

#Rotatable Bonds: 5

Polar Surface Area: 73.14

Molecular Species: NEUTRAL

HBA: 6

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 1.19

CX LogP: 2.84

CX LogD: 2.84

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.65

Np Likeness Score: -1.75

References

1. Kuduk SD, Skudlarek JW, Di Marco CN, Bruno JG, Pausch MA, O'Brien JA, Cabalu TD, Stevens J, Brunner J, Tannenbaum PL, Gotter AL, Winrow CJ, Renger JJ, Coleman PJ..  (2014)  Synthesis and evaluation of carbon-linked analogs of dual orexin receptor antagonist filorexant.,  24  (7): [PMID:24630562] [10.1016/j.bmcl.2014.02.026]

2.  (2013)  Pyridyl piperidine orexin receptor antagonists, 

3. Sun S, Fu J..  (2018)  Methyl-containing pharmaceuticals: Methylation in drug design.,  28  (20.0): [PMID:30243589] [10.1016/j.bmcl.2018.09.016]

Source

Source(2):

• Scientific Literature
• BindingDB Database