Benzo[b]thiophene-2-carboxylic Acid(1-{(S)-1-Benzyl-4-[4-(tetrahydropyran-4-ylmethyl)piperazin-1-yl]butylcarbamoyl}-cyclopentyl)amide

ID: ALA1083849

PubChem CID: 46236387

Max Phase: Preclinical

Molecular Formula: C36H48N4O3S

Molecular Weight: 616.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NC1(C(=O)N[C@@H](CCCN2CCN(CC3CCOCC3)CC2)Cc2ccccc2)CCCC1)c1cc2ccccc2s1

Standard InChI:  InChI=1S/C36H48N4O3S/c41-34(33-26-30-11-4-5-13-32(30)44-33)38-36(16-6-7-17-36)35(42)37-31(25-28-9-2-1-3-10-28)12-8-18-39-19-21-40(22-20-39)27-29-14-23-43-24-15-29/h1-5,9-11,13,26,29,31H,6-8,12,14-25,27H2,(H,37,42)(H,38,41)/t31-/m0/s1

Standard InChI Key:  IFLAJVCAIZJOPG-HKBQPEDESA-N

Molfile:  

     RDKit          2D

 44 49  0  0  0  0  0  0  0  0999 V2000
   18.3498  -20.1394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0623  -19.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8862  -18.9163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0648  -18.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7334  -19.5905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2042  -20.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9186  -20.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6331  -20.5542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9186  -19.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.0621  -20.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7765  -20.1417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.0621  -21.3792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.4910  -20.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2055  -20.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4910  -21.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2055  -21.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2014  -22.6177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9150  -23.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6305  -22.6176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6278  -21.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9136  -21.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9199  -20.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6344  -20.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.3489  -20.5542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3436  -21.3801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0539  -21.7925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7708  -21.3835    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.7728  -20.5576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0579  -20.1406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4837  -21.7987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1998  -21.3889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9090  -21.8092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6228  -21.4030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6302  -20.5776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9175  -20.1602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1974  -20.5682    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4487  -20.2228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1161  -21.3788    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.3092  -21.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8997  -20.8344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0768  -20.8321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6623  -21.5449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0769  -22.2617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8984  -22.2605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
 14 22  1  0
 10 11  1  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
  6 37  2  0
 17 18  1  0
  8  1  1  0
 37 40  1  0
 39 38  1  0
 38  6  1  0
 18 19  2  0
  4  5  1  0
 39 40  2  0
 19 20  1  0
 40 41  1  0
  1 10  1  0
 41 42  2  0
 20 21  2  0
 42 43  1  0
 21 16  1  0
 43 44  2  0
 44 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1083849

   N-[1-[[(2S)-5-[4-(oxan-4-ylmethyl)piperazin-1-yl]-1-phenylpentan-2-yl]carbamoyl]cyclopentyl]-1-benzothiophene-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: 616.87

Molecular Weight (Monoisotopic): 616.3447

AlogP: 5.50

#Rotatable Bonds: 12

Polar Surface Area: 73.91

Molecular Species: BASE

HBA: 6

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: 5.47

CX LogD: 4.04

Aromatic Rings: 3

Heavy Atoms: 44

QED Weighted: 0.28

Np Likeness Score: -1.01

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