2-(4-chloro-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide

ID: ALA1099084

PubChem CID: 9884133

Max Phase: Preclinical

Molecular Formula: C17H19ClN2OS

Molecular Weight: 334.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1nccs1)C(CC1CCCC1)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C17H19ClN2OS/c18-14-7-5-13(6-8-14)15(11-12-3-1-2-4-12)16(21)20-17-19-9-10-22-17/h5-10,12,15H,1-4,11H2,(H,19,20,21)

Standard InChI Key:  SGNFVZHFDYJMIW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -0.8703  -22.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5852  -22.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5852  -21.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8703  -23.3524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1554  -22.1166    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6442  -23.3456    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.5553  -22.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3087  -22.1914    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8610  -22.8029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4491  -23.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8703  -20.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7856  -20.0597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0235  -19.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4354  -20.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1169  -21.2138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2959  -22.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2959  -23.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0107  -23.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7256  -23.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7256  -22.5286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0107  -22.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4363  -23.7643    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  4  2  0
  1  5  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  6 10  1  0
  5  7  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 11 15  1  0
  3 11  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 16 21  2  0
 19 22  1  0
  2 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1099084

   2-(4-chloro-phenyl)-3-cyclopentyl-N-thiazol-2-yl-propionamide

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: 334.87

Molecular Weight (Monoisotopic): 334.0907

AlogP: 5.10

#Rotatable Bonds: 5

Polar Surface Area: 41.99

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.89

CX Basic pKa: ┄

CX LogP: 5.14

CX LogD: 5.02

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.83

Np Likeness Score: -1.29

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