US8969394, 25

ID: ALA3695944

PubChem CID: 24953626

Max Phase: Preclinical

Molecular Formula: C22H19Cl2NO3S

Molecular Weight: 448.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1sc(C)c(C(=O)NCc2ccc(C(=O)O)c(Cl)c2)c1Cc1cccc(Cl)c1

Standard InChI:  InChI=1S/C22H19Cl2NO3S/c1-12-18(9-14-4-3-5-16(23)8-14)20(13(2)29-12)21(26)25-11-15-6-7-17(22(27)28)19(24)10-15/h3-8,10H,9,11H2,1-2H3,(H,25,26)(H,27,28)

Standard InChI Key:  QDIPFKFTXNOJCG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    2.4245   -8.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1332   -7.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6332   -7.5468    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1017   -6.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2421   -5.7482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8912   -5.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8933   -3.7570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9336   -3.1588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5973    1.5031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5956    2.7031    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6375    0.9049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3383   -1.3500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6747   -6.1134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2541   -5.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1290   -6.6309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2940   -6.1565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4164   -7.1516    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1158   -8.6212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6929   -9.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4524  -10.2713    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4295   -8.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  1  0
 18 19  1  0
 18 20  2  0
 20 11  1  0
  6 21  1  0
 21  2  2  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  1  0
 27 29  2  0
 29 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3695944

   2-Chloro-4-[[[4-[(3-chlorophenyl)methyl]-2,5-dimethylthiophene-3-carbonyl]amino]methyl]benzoic acid

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: 448.37

Molecular Weight (Monoisotopic): 447.0463

AlogP: 5.89

#Rotatable Bonds: 6

Polar Surface Area: 66.40

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.06

CX Basic pKa: ┄

CX LogP: 6.80

CX LogD: 3.33

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: -1.21

References

1.  (2015)  Thiophenecarboxamide derivatives as EP4 receptor ligands, 

Source

Source(1):

• BindingDB Database