endo-2-(4-chlorophenyl)-N-((R)-3-(4-chlorophenyl)-1-(8-methyl-8-azabicyclo[3.2.1]octan-3-ylamino)-1-oxopropan-2-yl)-2-methylpropanamide

ID: ALA1774021

PubChem CID: 54581300

Max Phase: Preclinical

Molecular Formula: C27H33Cl2N3O2

Molecular Weight: 502.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1[C@@H]2CC[C@H]1C[C@@H](NC(=O)[C@@H](Cc1ccc(Cl)cc1)NC(=O)C(C)(C)c1ccc(Cl)cc1)C2

Standard InChI:  InChI=1S/C27H33Cl2N3O2/c1-27(2,18-6-10-20(29)11-7-18)26(34)31-24(14-17-4-8-19(28)9-5-17)25(33)30-21-15-22-12-13-23(16-21)32(22)3/h4-11,21-24H,12-16H2,1-3H3,(H,30,33)(H,31,34)/t21-,22+,23-,24-/m1/s1

Standard InChI Key:  YSQWQPAAOQGODI-UEQSERJNSA-N

Molfile:  

     RDKit          2D

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   12.8686  -16.9277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5824  -16.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5811  -15.6890    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2975  -16.9254    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   16.8028  -15.9678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3503  -15.2460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5476  -15.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.7583  -15.9583    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   11.4396  -16.9299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7245  -16.5185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4409  -17.7549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    9.3074  -18.1673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0178  -17.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3139  -14.3748    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.0785  -17.3471    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   12.8699  -17.7527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5850  -18.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5818  -18.9886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2961  -19.3999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0109  -18.9862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0070  -18.1569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2921  -17.7494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7266  -19.3966    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.8740  -18.1706    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.1292  -15.8000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1333  -15.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  6
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  9 24  1  1
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  2 26  1  1
  9 13  1  0
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 10 13  1  0
 27 28  2  0
  3  4  2  0
 28 29  1  0
 13 14  1  0
 29 30  2  0
 30 31  1  0
  1 15  1  0
 31 32  2  0
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  3  5  1  0
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  2  3  1  0
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 15 17  2  0
 16 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1774021

   2-(4-chlorophenyl)-N-[(2R)-3-(4-chlorophenyl)-1-[[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl]amino]-1-oxopropan-2-yl]-2-methylpropanamide

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: 502.49

Molecular Weight (Monoisotopic): 501.1950

AlogP: 4.74

#Rotatable Bonds: 7

Polar Surface Area: 61.44

Molecular Species: BASE

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.29

CX Basic pKa: 9.25

CX LogP: 5.01

CX LogD: 3.16

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.58

Np Likeness Score: -0.66

References

1. Napier S, Wishart G, Arbuckle W, Baker J, Barn D, Bingham M, Brown A, Byford A, Claxton C, Craighead M, Buchanan K, Fielding L, Gibson L, Goodwin R, Goutcher S, Irving N, MacSweeney C, Milne R, Mort C, Presland J, Sloan H, Thomson F, Turnbull Z, Young T..  (2011)  The discovery of novel 8-azabicyclo[3.2.1]octan-3-yl)-3-(4-chlorophenyl) propanamides as vasopressin V1A receptor antagonists.,  21  (10): [PMID:21458261] [10.1016/j.bmcl.2011.02.096]

Source

Source(1):

• Scientific Literature