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

ID: ALA1956438

Cas Number: 438473-43-9

PubChem CID: 4625719

Max Phase: Preclinical

Molecular Formula: C19H20N2O2S

Molecular Weight: 340.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(CCC(=O)Nc2sc3c(c2C#N)CCCC3)cc1

Standard InChI:  InChI=1S/C19H20N2O2S/c1-23-14-9-6-13(7-10-14)8-11-18(22)21-19-16(12-20)15-4-2-3-5-17(15)24-19/h6-7,9-10H,2-5,8,11H2,1H3,(H,21,22)

Standard InChI Key:  PZXFGPXLLSGRSI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   12.4677   -9.4580    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.1290   -8.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8652   -8.1847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7952   -8.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0373   -8.1941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4798   -7.5943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6772   -7.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4352   -8.5629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9956   -9.1683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3434   -7.5075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8213   -6.8337    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.8474   -9.3733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.5596   -8.9548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2781   -9.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5532   -8.1288    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2844  -10.1883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0030  -10.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0069  -11.4195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7246  -11.8270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4377  -11.4083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4287  -10.5781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7105  -10.1744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1568  -11.8149    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8684  -11.3954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  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
  3 10  1  0
 23 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1956438

   N-(3-cyano-4,5,6,7-tetrahydro-1-benzothiophen-2-yl)-3-(4-methoxyphenyl)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: 340.45

Molecular Weight (Monoisotopic): 340.1245

AlogP: 4.08

#Rotatable Bonds: 5

Polar Surface Area: 62.12

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.50

CX Basic pKa: ┄

CX LogP: 4.72

CX LogD: 4.72

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.89

Np Likeness Score: -1.84

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