5-(3-(4-(4-chlorophenyl)piperazine-1-carbonyl)isoxazol-5-yl)pyridin-2(1H)-one

ID: ALA4583561

PubChem CID: 155562142

Max Phase: Preclinical

Molecular Formula: C19H17ClN4O3

Molecular Weight: 384.82

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(c1cc(-c2ccc(=O)[nH]c2)on1)N1CCN(c2ccc(Cl)cc2)CC1

Standard InChI:  InChI=1S/C19H17ClN4O3/c20-14-2-4-15(5-3-14)23-7-9-24(10-8-23)19(26)16-11-17(27-22-16)13-1-6-18(25)21-12-13/h1-6,11-12H,7-10H2,(H,21,25)

Standard InChI Key:  WVSHWZGIXXFRSR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   10.2678  -21.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5604  -20.6126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5650  -19.7957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8617  -19.3867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1513  -19.7912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.1487  -20.6094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8565  -21.0230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4454  -19.3794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7359  -19.7848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4492  -18.5622    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9898  -19.4520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4402  -20.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8456  -20.7664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6456  -20.6001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6225  -20.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2214  -19.3363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4044  -19.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9889  -20.0345    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3963  -20.7484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2119  -20.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1717  -20.0288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2651  -21.8382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9717  -22.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6807  -21.8392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6787  -21.0178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9716  -20.6124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3886  -22.2474    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  7  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  8 10  2  0
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14  9  2  0
 12 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 15  2  0
 18 21  2  0
  1 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26  1  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4583561

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 384.82

Molecular Weight (Monoisotopic): 384.0989

AlogP: 2.65

#Rotatable Bonds: 3

Polar Surface Area: 82.44

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.17

CX Basic pKa: 2.69

CX LogP: 1.84

CX LogD: 1.84

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.75

Np Likeness Score: -1.98

References

1. Anan K, Masui M, Tazawa A, Tomida M, Haga Y, Kume M, Yamamoto S, Shinohara S, Tsuji H, Shimada S, Yagi S, Hasebe N, Kai H..  (2019)  Discovery of NR2B-selective antagonists via scaffold hopping and pharmacokinetic profile optimization.,  29  (9): [PMID:30833109] [10.1016/j.bmcl.2019.02.017]

Source

Source(1):

• Scientific Literature