2-[3-Cyclopentyl-2-(3,4-dichlorophenyl)-propionylamino]-thiazole-4-carboxylic acid

ID: ALA1098973

PubChem CID: 9866410

Max Phase: Preclinical

Molecular Formula: C18H18Cl2N2O3S

Molecular Weight: 413.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1csc(NC(=O)C(CC2CCCC2)c2ccc(Cl)c(Cl)c2)n1

Standard InChI:  InChI=1S/C18H18Cl2N2O3S/c19-13-6-5-11(8-14(13)20)12(7-10-3-1-2-4-10)16(23)22-18-21-15(9-26-18)17(24)25/h5-6,8-10,12H,1-4,7H2,(H,24,25)(H,21,22,23)

Standard InChI Key:  FDQRYJSBXWMVHG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    0.6173   -2.4907    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.5325   -1.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2869   -1.3349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8400   -1.9472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4275   -2.6631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6582   -1.8624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1429   -2.5320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9957   -1.1079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1834   -1.2600    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8992   -1.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8992   -2.4975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6109   -1.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6109   -0.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3268   -1.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3268   -2.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0385   -2.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7544   -2.4975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7544   -1.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0385   -1.2600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4702   -2.9100    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.0385   -3.7350    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.8992   -0.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8102    0.7998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0042    0.9722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4083    0.2563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1448   -0.3559    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  2  0
  6  8  1  0
  4  6  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 17 20  1  0
 16 21  1  0
 12 14  1  0
  9 10  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 22 26  1  0
 13 22  1  0
  2  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1098973

   2-[3-Cyclopentyl-2-(3,4-dichlorophenyl)-propionylamino]-thiazole-4-carboxylic 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: 413.33

Molecular Weight (Monoisotopic): 412.0415

AlogP: 5.45

#Rotatable Bonds: 6

Polar Surface Area: 79.29

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.16

CX Basic pKa: ┄

CX LogP: 5.78

CX LogD: 2.22

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.66

Np Likeness Score: -1.14

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]

2. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

Source

Source(2):

• Scientific Literature
• AstraZeneca Deposited Data