(3aR,4R,7S,7aR)-3-(pyridin-3-yl)-N-(p-tolyl)-4,5,6,7-tetrahydro-4,7-methanobenzo[d]isoxazole-7a(3aH)-carboxamide

ID: ALA5192747

PubChem CID: 168286129

Max Phase: Preclinical

Molecular Formula: C21H21N3O2

Molecular Weight: 347.42

Names and Identifiers

Canonical SMILES:  Cc1ccc(NC(=O)[C@]23ON=C(c4cccnc4)[C@H]2[C@@H]2CC[C@H]3C2)cc1

Standard InChI:  InChI=1S/C21H21N3O2/c1-13-4-8-17(9-5-13)23-20(25)21-16-7-6-14(11-16)18(21)19(24-26-21)15-3-2-10-22-12-15/h2-5,8-10,12,14,16,18H,6-7,11H2,1H3,(H,23,25)/t14-,16+,18-,21-/m1/s1

Standard InChI Key:  QTQGVRORJQFHEJ-HRWHDRTOSA-N

Molfile:  

 
     RDKit          2D

 29 33  0  0  0  0  0  0  0  0999 V2000
    2.7241    0.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8991    0.6818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4886    1.3934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8988    2.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7204    2.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1304    1.3953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1311    2.8136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4884   -0.0294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6670   -0.0294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2602    0.6841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2524   -0.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687   -0.8299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7369   -0.7217    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8486   -1.6985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0940   -2.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3933   -2.8136    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9104   -2.2437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3977   -1.5826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2349   -1.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7836   -2.0110    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0103   -1.1560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0103   -0.3388    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2138   -0.0910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7182   -1.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7182   -2.3821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4215   -2.7900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1311   -2.3857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1311   -1.5652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4232   -1.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  3  1  0
  5  4  2  0
  6  5  1  0
  1  6  2  0
  5  7  1  0
  8  2  1  0
  9  8  1  0
  9 10  2  0
 11  9  1  1
 11 12  1  0
 12 13  1  6
 12 14  1  0
 15 14  1  0
 15 16  1  6
 15 17  1  0
 17 18  1  0
 18 12  1  0
 19 15  1  0
 19 11  1  0
 19 20  1  1
 21 19  1  0
 21 22  2  0
 22 23  1  0
 23 11  1  0
 21 24  1  0
 25 24  2  0
 26 25  1  0
 27 26  2  0
 28 27  1  0
 29 28  2  0
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5192747

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 347.42

Molecular Weight (Monoisotopic): 347.1634

AlogP: 3.55

#Rotatable Bonds: 3

Polar Surface Area: 63.58

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.87

CX Basic pKa: 4.21

CX LogP: 3.50

CX LogD: 3.50

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.92

Np Likeness Score: -0.25

References

1. Yin L, Pan Y, Xue Y, Chen X, You T, Huang J, Xu Q, Hu Q..  (2022)  Design, Synthesis, and Biological Evaluations of Pyridyl 4,5,6,7-Tetrahydro-4,7-Methanobenzo[d]isoxazoles as Potent and Selective Inhibitors of 11β-Hydroxylase.,  65  (17.0): [PMID:35975976] [10.1021/acs.jmedchem.2c01037]

Source

Source(1):

• Scientific Literature