US8969394, 6

ID: ALA3695938

PubChem CID: 24952579

Max Phase: Preclinical

Molecular Formula: C22H18Cl3NO3S

Molecular Weight: 482.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc([C@H](C)NC(=O)c2c(Cl)sc(Cl)c2Cc2cccc(Cl)c2)cc1

Standard InChI:  InChI=1S/C22H18Cl3NO3S/c1-12(14-6-8-15(9-7-14)22(28)29-2)26-21(27)18-17(19(24)30-20(18)25)11-13-4-3-5-16(23)10-13/h3-10,12H,11H2,1-2H3,(H,26,27)/t12-/m0/s1

Standard InChI Key:  SMQMCNFEOUIGIM-LBPRGKRZSA-N

Molfile:  

     RDKit          2D

 30 32  0  0  1  0  0  0  0  0999 V2000
    3.6331   -3.6060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 O   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
    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
    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
   -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
   -2.5998    1.4987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6380    0.8969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6028    2.9995    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9036    3.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9418    3.1464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9066    5.2489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1200    6.1089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2591    5.7313    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -4.6564    7.5354    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1564    7.5353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4510    8.5061    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.6930    6.1087    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2727    5.6318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9742    4.1609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4471    3.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7424    2.2107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3835    1.2196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8048    1.6991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7055    0.9062    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.1001    3.1697    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  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  8 11  1  0
 11 12  1  6
 11 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  2  0
 22 16  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 28 30  2  0
 30 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3695938

   methyl 4-[(1S)-1-({[2,5-dichloro-4-(3-chlorobenzyl)-3-thienyl]carbonyl}amino)ethyl]benzoate

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: 482.82

Molecular Weight (Monoisotopic): 481.0073

AlogP: 6.58

#Rotatable Bonds: 6

Polar Surface Area: 55.40

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.57

CX Basic pKa: ┄

CX LogP: 7.21

CX LogD: 7.21

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.40

Np Likeness Score: -0.97

References

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

Source

Source(1):

• BindingDB Database