1-(4-{3-[4-(6-Fluoro-benzo[d]isoxazol-3-yl)-piperidin-1-yl]-propylamino}-3-methoxy-phenyl)-ethanone

ID: ALA14727

PubChem CID: 10387699

Max Phase: Preclinical

Molecular Formula: C24H28FN3O3

Molecular Weight: 425.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(C(C)=O)ccc1NCCCN1CCC(c2noc3cc(F)ccc23)CC1

Standard InChI:  InChI=1S/C24H28FN3O3/c1-16(29)18-4-7-21(23(14-18)30-2)26-10-3-11-28-12-8-17(9-13-28)24-20-6-5-19(25)15-22(20)31-27-24/h4-7,14-15,17,26H,3,8-13H2,1-2H3

Standard InChI Key:  MDVOAKSPEFVXPL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    1.4792  -13.9000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4792  -13.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0500  -13.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7625  -14.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0417  -13.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7625   -8.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2375  -11.3292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708  -12.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6708  -14.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9625   -8.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -9.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667  -12.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3417   -8.2917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5917  -10.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9667   -9.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1375   -7.4917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3792  -10.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3833  -13.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8625  -12.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542  -11.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417  -11.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4417  -12.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0042  -10.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3833  -13.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5792   -9.0167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0958  -14.3125    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    3.8250  -10.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167  -10.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2042  -10.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1417   -8.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3667   -8.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  1  1  0
  5  4  1  0
  6 15  2  0
  7 21  1  0
  8  3  2  0
  9  5  2  0
 10 11  2  0
 11 14  1  0
 12  2  1  0
 13  6  1  0
 14 23  1  0
 15 17  1  0
 16 13  2  0
 17 14  2  0
 18  9  1  0
 19 12  1  0
 20 12  1  0
 21 20  1  0
 22 19  1  0
 23 29  1  0
 24  8  1  0
 25 11  1  0
 26 18  1  0
 27  7  1  0
 28 27  1  0
 29 28  1  0
 30 13  1  0
 31 25  1  0
  3  5  1  0
 22  7  1  0
 24 18  2  0
 10  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA14727

   1-(4-{3-[4-(6-Fluoro-benzo[d]isoxazol-3-yl)-piperidin-1-yl]-propylamino}-3-methoxy-phenyl)-ethanone

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: 425.50

Molecular Weight (Monoisotopic): 425.2115

AlogP: 4.86

#Rotatable Bonds: 8

Polar Surface Area: 67.60

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.10

CX LogP: 2.85

CX LogD: 2.07

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.41

Np Likeness Score: -1.49

References

1. Strupczewski JT, Bordeau KJ, Chiang Y, Glamkowski EJ, Conway PG, Corbett R, Hartman HB, Szewczak MR, Wilmot CA, Helsley GC..  (1995)  3-[[(Aryloxy)alkyl]piperidinyl]-1,2-benzisoxazoles as D2/5-HT2 antagonists with potential atypical antipsychotic activity: antipsychotic profile of iloperidone (HP 873).,  38  (7): [PMID:7707315] [10.1021/jm00007a009]

Source

Source(1):

• Scientific Literature