US8969394, 5

ID: ALA3695937

PubChem CID: 24178408

Max Phase: Preclinical

Molecular Formula: C21H16Br2ClNO3S

Molecular Weight: 557.69

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H16Br2ClNO3S/c1-11(13-5-7-14(8-6-13)21(27)28)25-20(26)17-16(18(22)29-19(17)23)10-12-3-2-4-15(24)9-12/h2-9,11H,10H2,1H3,(H,25,26)(H,27,28)/t11-/m0/s1

Standard InChI Key:  KMCFCSKMVIRYBI-NSHDSACASA-N

Molfile:  

     RDKit          2D

 29 31  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 Br  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 Br  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
   -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
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 20 14  1  0
  2 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 24 27  1  0
 27 28  2  0
 27 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3695937

   4-[(1S)-1-({[2,5-dibromo-4-(3-chlorobenzyl)-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: 557.69

Molecular Weight (Monoisotopic): 554.8906

AlogP: 6.71

#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: 7.19

CX LogD: 4.07

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.35

Np Likeness Score: -0.90

References

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

Source

Source(1):

• BindingDB Database