(RS)-(4,4-difluoro-3-(quinolin-2-yloxy)piperidin-1-yl)(3-methoxyphenyl)methanone

ID: ALA3978250

PubChem CID: 77105014

Max Phase: Preclinical

Molecular Formula: C22H20F2N2O3

Molecular Weight: 398.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(C(=O)N2CCC(F)(F)C(Oc3ccc4ccccc4n3)C2)c1

Standard InChI:  InChI=1S/C22H20F2N2O3/c1-28-17-7-4-6-16(13-17)21(27)26-12-11-22(23,24)19(14-26)29-20-10-9-15-5-2-3-8-18(15)25-20/h2-10,13,19H,11-12,14H2,1H3

Standard InChI Key:  QZXSVMSMRJTFPZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   17.4458   -7.8748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8542   -7.1624    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.3436  -10.7514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3425  -11.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0505  -11.9799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0487  -10.3425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7574  -10.7478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7607  -11.5730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4663  -10.3300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1777  -10.7323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4591   -9.5128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1635   -9.0959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1582   -8.2823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7428   -8.2898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7465   -9.1096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8638   -7.8700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   19.5729   -9.0892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2819   -9.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2719   -7.8592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.9814   -8.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9844   -9.0781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6930   -9.4827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3991   -9.0706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3922   -8.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6831   -7.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0483  -12.7932    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7552  -13.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 12 16  1  0
 13 14  1  0
 14  2  1  0
  2 15  1  0
 15 16  1  0
 14 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 23  2  0
 22 21  2  0
 21 18  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 28 29  1  0
  6 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3978250

   (4,4-Difluoro-3-quinolin-2-yloxypiperidin-1-yl)-(3-methoxyphenyl)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: 398.41

Molecular Weight (Monoisotopic): 398.1442

AlogP: 4.17

#Rotatable Bonds: 4

Polar Surface Area: 51.66

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.22

CX LogP: 4.37

CX LogD: 4.37

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.66

Np Likeness Score: -1.01

References

1. Stump CA, Cooke AJ, Bruno J, Cabalu TD, Gotter AL, Harell CM, Kuduk SD, McDonald TP, O'Brien J, Renger JJ, Williams PD, Winrow CJ, Coleman PJ..  (2016)  Discovery of highly potent and selective orexin 1 receptor antagonists (1-SORAs) suitable for in vivo interrogation of orexin 1 receptor pharmacology.,  26  (23): [PMID:27818110] [10.1016/j.bmcl.2016.10.019]

Source

Source(1):

• Scientific Literature