US8969394, 21

ID: ALA3695943

PubChem CID: 24953284

Max Phase: Preclinical

Molecular Formula: C22H16Cl2F3NO3S

Molecular Weight: 502.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)c1c(Cl)sc(Cl)c1Cc1cccc(C(F)(F)F)c1)c1ccc(C(=O)O)cc1

Standard InChI:  InChI=1S/C22H16Cl2F3NO3S/c1-11(13-5-7-14(8-6-13)21(30)31)28-20(29)17-16(18(23)32-19(17)24)10-12-3-2-4-15(9-12)22(25,26)27/h2-9,11H,10H2,1H3,(H,28,29)(H,30,31)/t11-/m0/s1

Standard InChI Key:  ASHWHAHRKQFQAR-NSHDSACASA-N

Molfile:  

     RDKit          2D

 32 34  0  0  1  0  0  0  0  0999 V2000
   -2.6567   -2.2146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7546   -1.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3335   -1.9059    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0400   -3.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9421   -4.1691    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3786   -3.8595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8372   -5.2877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1285   -6.2561    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.3372   -5.2929    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.8056   -3.8679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9460   -3.4943    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    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
    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
   -2.5988   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6384   -0.9011    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5984   -2.7004    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6377   -2.1009    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0480    0.0486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9221    1.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2174    2.5105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6387    2.9901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7646    1.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4693    0.5283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9372    4.4609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0747    4.8429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0378    5.2553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12  6  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 20 23  1  0
  2 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 27 30  1  0
 30 31  2  0
 30 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3695943

   4-[(1S)-1-[[2,5-dichloro-4-[[3-(trifluoromethyl)phenyl]methyl]thiophene-3-carbonyl]amino]ethyl]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: 502.34

Molecular Weight (Monoisotopic): 501.0180

AlogP: 6.85

#Rotatable Bonds: 6

Polar Surface Area: 66.40

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.06

CX Basic pKa: ┄

CX LogP: 7.14

CX LogD: 4.02

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.39

Np Likeness Score: -1.02

References

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

Source

Source(1):

• BindingDB Database