2-[3-Cyclopentyl-2-(3,4-dichlorophenyl)-propionylamino]-thiazol-4-yl}-acetic acid ethyl ester

ID: ALA1098742

PubChem CID: 46221804

Max Phase: Preclinical

Molecular Formula: C21H24Cl2N2O3S

Molecular Weight: 455.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)Cc1csc(NC(=O)C(CC2CCCC2)c2ccc(Cl)c(Cl)c2)n1

Standard InChI:  InChI=1S/C21H24Cl2N2O3S/c1-2-28-19(26)11-15-12-29-21(24-15)25-20(27)16(9-13-5-3-4-6-13)14-7-8-17(22)18(23)10-14/h7-8,10,12-13,16H,2-6,9,11H2,1H3,(H,24,25,27)

Standard InChI Key:  MLKRLDYABJPSAM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   19.1272   -9.2611    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.0425   -8.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7918   -8.1070    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3441   -8.7183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9322   -9.4332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6493   -9.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1653   -8.6337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3122  -10.0516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.4663   -9.2134    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3276   -8.0322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6128   -8.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6128   -9.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8979   -8.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8979   -7.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1872   -8.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1872   -9.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4723   -9.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7617   -9.2680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7617   -8.4441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4724   -8.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0468   -9.6799    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   15.4723  -10.5037    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.6128   -6.7964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6975   -5.9752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5066   -5.8031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9185   -6.5179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3662   -7.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9504   -9.8821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7715   -9.7932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  1  5  1  0
  6  7  1  0
  6  8  2  0
  6  9  1  0
  4  7  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
 18 21  1  0
 17 22  1  0
 13 15  1  0
 10 11  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 23 27  1  0
 14 23  1  0
  2 10  1  0
 28 29  1  0
  9 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1098742

   {2-[3-Cyclopentyl-2-(3,4-dichlorophenyl)-propionylamino]-thiazol-4-yl}-acetic acid ethyl ester

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: 455.41

Molecular Weight (Monoisotopic): 454.0885

AlogP: 5.86

#Rotatable Bonds: 8

Polar Surface Area: 68.29

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.88

CX Basic pKa: ┄

CX LogP: 6.27

CX LogD: 6.15

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.51

Np Likeness Score: -1.40

References

1. Haynes NE, Corbett WL, Bizzarro FT, Guertin KR, Hilliard DW, Holland GW, Kester RF, Mahaney PE, Qi L, Spence CL, Tengi J, Dvorozniak MT, Railkar A, Matschinsky FM, Grippo JF, Grimsby J, Sarabu R..  (2010)  Discovery, structure-activity relationships, pharmacokinetics, and efficacy of glucokinase activator (2R)-3-cyclopentyl-2-(4-methanesulfonylphenyl)-N-thiazol-2-yl-propionamide (RO0281675).,  53  (9): [PMID:20405948] [10.1021/jm100039a]

Source

Source(1):

• Scientific Literature