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

ID: ALA5195876

PubChem CID: 168292485

Max Phase: Preclinical

Molecular Formula: C21H21N3O2

Molecular Weight: 347.42

Names and Identifiers

Canonical SMILES:  Cc1ccccc1NC(=O)[C@]12ON=C(c3cccnc3)[C@H]1[C@@H]1CC[C@H]2C1

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

Standard InChI Key:  XRNHAKBGQSAPJY-HRWHDRTOSA-N

Molfile:  

 
     RDKit          2D

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    1.4869    1.7493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8971    2.4582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7188    2.4582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1288    1.7511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4867    0.3262    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6652    0.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2584    1.0399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2506   -0.3827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0670   -0.4743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7352   -0.3661    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8468   -1.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0922   -1.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3951   -2.4582    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9086   -1.8883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3959   -1.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2367   -1.0441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7855   -1.6555    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.0123    0.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2156    0.2646    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7201   -1.2093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7201   -2.0266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4236   -2.4346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1332   -2.0303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1332   -1.2097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4253   -0.8013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1332    0.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 14 13  1  0
 14 15  1  6
 14 16  1  0
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 17 11  1  0
 18 14  1  0
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 18 19  1  1
 20 18  1  0
 20 21  2  0
 21 22  1  0
 22 10  1  0
 20 23  1  0
 24 23  2  0
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 27 26  1  0
 28 27  2  0
 23 28  1  0
  1 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5195876

   ---

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: 12.74

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: -0.33

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