Biphenyl-4-carboxylic Acid(1-{(S)-1-Benzyl-4-[4-(tetrahydropyran-4-ylmethyl)piperazin-1-yl]butylcarbamoyl}cyclopentyl)-amide

ID: ALA1083560

PubChem CID: 46237957

Max Phase: Preclinical

Molecular Formula: C40H52N4O3

Molecular Weight: 636.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC1(C(=O)N[C@@H](CCCN2CCN(CC3CCOCC3)CC2)Cc2ccccc2)CCCC1)c1ccc(-c2ccccc2)cc1

Standard InChI:  InChI=1S/C40H52N4O3/c45-38(36-17-15-35(16-18-36)34-12-5-2-6-13-34)42-40(21-7-8-22-40)39(46)41-37(30-32-10-3-1-4-11-32)14-9-23-43-24-26-44(27-25-43)31-33-19-28-47-29-20-33/h1-6,10-13,15-18,33,37H,7-9,14,19-31H2,(H,41,46)(H,42,45)/t37-/m0/s1

Standard InChI Key:  PGRZDFUKUNJXDD-QNGWXLTQSA-N

Molfile:  

     RDKit          2D

 47 52  0  0  0  0  0  0  0  0999 V2000
   18.2956    0.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0081    0.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8320    1.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0106    1.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6792    0.5637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1500   -0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8645    0.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5789   -0.4000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8645    0.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0079   -0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7224    0.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0079   -1.2250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4368   -0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1513    0.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4368   -1.2250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1513   -1.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1472   -2.4636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8609   -2.8760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5763   -2.4634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5737   -1.6342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8594   -1.2255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8658   -0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5802    0.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2947   -0.4000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2894   -1.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9998   -1.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7167   -1.2294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7186   -0.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0037    0.0136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4296   -1.6446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1456   -1.2348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.8548   -1.6551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5687   -1.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.5761   -0.4235    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.8633   -0.0061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1432   -0.4140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4360    0.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7220   -0.3964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7216   -1.2222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4411   -1.6346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1521   -1.2204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0101   -1.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2948   -1.2230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5813   -1.6357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5820   -2.4616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3020   -2.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0125   -2.4579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 22 23  1  0
  1  2  1  0
 23 24  1  0
 24 25  1  0
 10 12  2  0
 13 11  1  0
  6  7  1  0
 13 14  1  0
 24 29  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
  2  3  1  0
 27 30  1  0
 13 15  1  1
 30 31  1  0
 31 32  1  0
  7  8  1  0
 15 16  1  0
  3  4  1  0
 16 17  2  0
  7  9  2  0
 31 36  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 17 18  1  0
  6 37  2  0
  8  1  1  0
 37 38  1  0
 18 19  2  0
 38 39  2  0
  4  5  1  0
 39 40  1  0
 19 20  1  0
 40 41  2  0
 41  6  1  0
  1 10  1  0
 20 21  2  0
 42 43  2  0
 21 16  1  0
 43 44  1  0
  5  1  1  0
 44 45  2  0
 14 22  1  0
 45 46  1  0
 10 11  1  0
 46 47  2  0
 47 42  1  0
 39 42  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1083560

   N-[1-[[(2S)-5-[4-(oxan-4-ylmethyl)piperazin-1-yl]-1-phenylpentan-2-yl]carbamoyl]cyclopentyl]-4-phenylbenzamide

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: 636.88

Molecular Weight (Monoisotopic): 636.4039

AlogP: 5.95

#Rotatable Bonds: 13

Polar Surface Area: 73.91

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: ┄

CX Basic pKa: 8.82

CX LogP: 6.11

CX LogD: 4.68

Aromatic Rings: 3

Heavy Atoms: 47

QED Weighted: 0.24

Np Likeness Score: -0.71

References

1. Fattori D, Porcelloni M, D'Andrea P, Catalioto RM, Ettorre A, Giuliani S, Marastoni E, Mauro S, Meini S, Rossi C, Altamura M, Maggi CA..  (2010)  Structure-activity relationships of 6-methyl-benzo[b]thiophene-2-carboxylic acid (1-[(S)-1-benzyl-4-[4-(tetrahydropyran-4-ylmethyl)piperazin-1-yl]butylcarbamoyl]cyclopentyl)amide, potent antagonist of the neurokinin-2 receptor.,  53  (10): [PMID:20408549] [10.1021/jm100176s]

Source

Source(1):

• Scientific Literature