US8969394, 9

ID: ALA3695940

PubChem CID: 24952925

Max Phase: Preclinical

Molecular Formula: C21H16Cl3NO4S

Molecular Weight: 484.79

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H](NC(=O)c1c(Cl)sc(Cl)c1C(O)c1cccc(Cl)c1)c1ccc(C(=O)O)cc1

Standard InChI:  InChI=1S/C21H16Cl3NO4S/c1-10(11-5-7-12(8-6-11)21(28)29)25-20(27)16-15(18(23)30-19(16)24)17(26)13-3-2-4-14(22)9-13/h2-10,17,26H,1H3,(H,25,27)(H,28,29)/t10-,17?/m0/s1

Standard InChI Key:  YJEXRJWDVWQMEX-YOZOHBORSA-N

Molfile:  

     RDKit          2D

 30 32  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
    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
   -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
   -2.0480    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
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
 21 15  1  0
  2 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 25 28  1  0
 28 29  2  0
 28 30  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3695940

   4-{(1S)-1-[({2,5-dichloro-4-[(3-chlorophenyl)(hydroxy)methyl]-3-thienyl}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: 484.79

Molecular Weight (Monoisotopic): 482.9866

AlogP: 5.98

#Rotatable Bonds: 6

Polar Surface Area: 86.63

Molecular Species: ACID

HBA: 4

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.06

CX Basic pKa: ┄

CX LogP: 5.79

CX LogD: 2.67

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.40

Np Likeness Score: -0.80

References

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

Source

Source(1):

• BindingDB Database