3-(4-chlorophenyl)-N-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)propanamide

ID: ALA1956439

PubChem CID: 19220887

Max Phase: Preclinical

Molecular Formula: C18H17ClN2OS

Molecular Weight: 344.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1c(NC(=O)CCc2ccc(Cl)cc2)sc2c1CCCC2

Standard InChI:  InChI=1S/C18H17ClN2OS/c19-13-8-5-12(6-9-13)7-10-17(22)21-18-15(11-20)14-3-1-2-4-16(14)23-18/h5-6,8-9H,1-4,7,10H2,(H,21,22)

Standard InChI Key:  AOWKQMUGAQZWET-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -3.0097  -14.0125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3485  -13.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6122  -12.7394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6821  -13.5358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4401  -12.7488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9975  -12.1490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8000  -12.3305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0421  -13.1175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4816  -13.7229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1341  -12.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6562  -11.3885    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6301  -13.9278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9181  -13.5094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1995  -13.9168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9244  -12.6834    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1932  -14.7428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5252  -15.1503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5292  -15.9738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2468  -16.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9599  -15.9627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9509  -15.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2326  -14.7289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6789  -16.3692    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  3 10  1  0
  1  2  1  0
  2 12  1  0
  2  3  2  0
 12 13  1  0
  3  5  1  0
 13 14  1  0
  4  5  2  0
 13 15  2  0
  4  9  1  0
 14 16  1  0
  5  6  1  0
 16 17  1  0
  6  7  1  0
 17 18  2  0
  7  8  1  0
 18 19  1  0
  8  9  1  0
 19 20  2  0
  4  1  1  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 10 11  3  0
 20 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1956439

   3-(4-chlorophenyl)-N-(3-cyano-4,5,6,7-tetrahydro-1-benzothiophen-2-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: 344.87

Molecular Weight (Monoisotopic): 344.0750

AlogP: 4.72

#Rotatable Bonds: 4

Polar Surface Area: 52.89

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.50

CX Basic pKa: ┄

CX LogP: 5.48

CX LogD: 5.48

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.87

Np Likeness Score: -2.15

References

1. Harikrishnan LS, Srivastava N, Kayser LE, Nirschl DS, Kumaragurubaran K, Roy A, Gupta A, Karmakar S, Karatt T, Mathur A, Burford NT, Chen J, Kong Y, Cvijic M, Cooper CB, Poss MA, Trainor GL, Wong TW..  (2012)  Identification and optimization of small molecule antagonists of vasoactive intestinal peptide receptor-1 (VIPR1).,  22  (6): [PMID:22365758] [10.1016/j.bmcl.2012.01.082]

Source

Source(1):

• Scientific Literature