(R)-endo-3-(4-chlorophenyl)-2-(2-(4-methoxyphenyl)acetamido)-N-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)propanamide

ID: ALA1774020

PubChem CID: 54587188

Max Phase: Preclinical

Molecular Formula: C26H32ClN3O3

Molecular Weight: 470.01

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CC(=O)N[C@H](Cc2ccc(Cl)cc2)C(=O)N[C@H]2C[C@H]3CC[C@@H](C2)N3C)cc1

Standard InChI:  InChI=1S/C26H32ClN3O3/c1-30-21-9-10-22(30)16-20(15-21)28-26(32)24(13-17-3-7-19(27)8-4-17)29-25(31)14-18-5-11-23(33-2)12-6-18/h3-8,11-12,20-22,24H,9-10,13-16H2,1-2H3,(H,28,32)(H,29,31)/t20-,21+,22-,24-/m1/s1

Standard InChI Key:  HQFLWOURXMVMMC-JTOYRKQZSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
   -0.6674  -15.8913    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0477  -16.3027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7615  -15.8890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7603  -15.0640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4767  -16.3004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1905  -15.8868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9820  -15.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5295  -14.6210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7268  -14.5410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6913  -16.1222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9055  -16.3672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1351  -15.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9375  -15.3333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1458  -14.6250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3812  -16.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0963  -15.8935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3799  -17.1299    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8102  -16.3071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5211  -15.8923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2344  -16.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2336  -17.1311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5134  -17.5423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8030  -17.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4930  -13.7498    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2577  -16.7221    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0490  -17.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7641  -17.5390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7610  -18.3636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4753  -18.7749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1901  -18.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1861  -17.5319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4713  -17.1244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9058  -18.7716    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.9468  -17.5456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6625  -17.1352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15 17  2  0
  6  5  1  6
 16 18  1  0
  7  8  1  0
 18 19  2  0
  8  9  1  0
 19 20  1  0
  7 10  1  0
 20 21  2  0
 11  6  1  0
 21 22  1  0
  6 12  1  0
 22 23  2  0
 23 18  1  0
 12  9  1  0
  9 24  1  1
 10 11  1  0
 10 25  1  1
  1  2  1  0
  2 26  1  1
  9 13  1  0
 26 27  1  0
 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
 32 27  1  0
  3  5  1  0
 30 33  1  0
 15 16  1  0
 21 34  1  0
  2  3  1  0
 34 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1774020

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

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: 470.01

Molecular Weight (Monoisotopic): 469.2132

AlogP: 3.36

#Rotatable Bonds: 8

Polar Surface Area: 70.67

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.48

CX Basic pKa: 9.25

CX LogP: 3.15

CX LogD: 1.30

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.62

Np Likeness Score: -0.65

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