N-(4-chlorophenyl)-8-(2,6-difluorobenzoyl)-2,8-diazaspiro[4.5]decane-2-carboxamide

ID: ALA2436562

PubChem CID: 72376037

Max Phase: Preclinical

Molecular Formula: C22H22ClF2N3O2

Molecular Weight: 433.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc(Cl)cc1)N1CCC2(CCN(C(=O)c3c(F)cccc3F)CC2)C1

Standard InChI:  InChI=1S/C22H22ClF2N3O2/c23-15-4-6-16(7-5-15)26-21(30)28-13-10-22(14-28)8-11-27(12-9-22)20(29)19-17(24)2-1-3-18(19)25/h1-7H,8-14H2,(H,26,30)

Standard InChI Key:  DLEGHEGQLWIBRQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    7.8493   -5.3217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2568   -6.0301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0699   -6.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4795   -5.3266    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0719   -4.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2548   -4.6123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1336   -5.0494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8413   -4.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5490   -5.0494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8413   -3.8236    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6385   -5.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4378   -6.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2996   -4.7122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2967   -5.3291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7032   -6.0380    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7073   -4.6226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5231   -4.6297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9338   -3.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5272   -3.2142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7058   -3.2144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2989   -3.9206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9274   -5.3399    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.4817   -3.9224    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.4259   -4.6408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4301   -3.8242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7232   -3.4157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0145   -3.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0172   -4.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7246   -5.0506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3036   -3.4196    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  6  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  7  8  1  0
  8  9  1  0
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  1 13  1  0
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  4 14  1  0
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 16 17  2  0
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 19 20  1  0
 20 21  2  0
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 21 23  1  0
  7 24  1  0
 24 25  2  0
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 27 28  1  0
 28 29  2  0
 29 24  1  0
 27 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2436562

   N-(4-chlorophenyl)-8-(2,6-difluorobenzoyl)-2,8-diazaspiro[4.5]decane-2-carboxamide

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: 433.89

Molecular Weight (Monoisotopic): 433.1369

AlogP: 4.78

#Rotatable Bonds: 2

Polar Surface Area: 52.65

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.38

CX Basic pKa: ┄

CX LogP: 3.69

CX LogD: 3.69

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.74

Np Likeness Score: -1.61

References

1. Kato Y, Fuchi N, Saburi H, Nishimura Y, Watanabe A, Yagi M, Nakadera Y, Higashi E, Yamada M, Aoki T..  (2013)  Discovery of 2,8-diazaspiro[4.5]decane-based trisubstituted urea derivatives as highly potent soluble epoxide hydrolase inhibitors and orally active drug candidates for treating hypertension.,  23  (21): [PMID:24035338] [10.1016/j.bmcl.2013.08.054]

Source

Source(1):

• Scientific Literature