3-(4-(4-chlorophenyl)thiazol-2-yl)-1-(2,5-dimethoxyphenyl)-6,7-dihydro-1H-cyclopenta[b]pyridine-2,5-dione

ID: ALA4876746

PubChem CID: 137548263

Max Phase: Preclinical

Molecular Formula: C25H19ClN2O4S

Molecular Weight: 478.96

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(OC)c(-n2c3c(cc(-c4nc(-c5ccc(Cl)cc5)cs4)c2=O)C(=O)CC3)c1

Standard InChI:  InChI=1S/C25H19ClN2O4S/c1-31-16-7-10-23(32-2)21(11-16)28-20-8-9-22(29)17(20)12-18(25(28)30)24-27-19(13-33-24)14-3-5-15(26)6-4-14/h3-7,10-13H,8-9H2,1-2H3

Standard InChI Key:  DMVLGXPZEVXHOW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   24.2106   -4.2089    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9281   -3.8014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9316   -2.9756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2176   -2.5573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6409   -4.2182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5011   -3.7953    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5047   -2.9730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7239   -2.7156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2376   -3.3788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7181   -4.0459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4720   -1.9291    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6439   -2.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3966   -2.9073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9524   -2.2965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5432   -1.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7346   -1.7467    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.2061   -5.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4870   -5.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4819   -6.2666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1954   -6.6844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9152   -6.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9167   -5.4474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7704   -2.3866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1015   -3.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9214   -3.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4112   -2.5692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0751   -1.8103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2561   -1.7230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7643   -6.6751    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0517   -6.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6330   -5.0365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3470   -5.4515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2322   -2.6589    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  7  4  1  0
  6  1  1  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  2  5  2  0
  6  7  2  0
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  9 10  1  0
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  8 11  2  0
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 15 16  1  0
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  3 12  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
  1 17  1  0
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 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 14 23  1  0
 19 29  1  0
 29 30  1  0
 22 31  1  0
 31 32  1  0
 26 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4876746

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 478.96

Molecular Weight (Monoisotopic): 478.0754

AlogP: 5.43

#Rotatable Bonds: 5

Polar Surface Area: 70.42

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.76

CX LogD: 4.76

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.38

Np Likeness Score: -1.04

References

1. Rohde JM, Karavadhi S, Pragani R, Liu L, Fang Y, Zhang W, McIver A, Zheng H, Liu Q, Davis MI, Urban DJ, Lee TD, Cheff DM, Hollingshead M, Henderson MJ, Martinez NJ, Brimacombe KR, Yasgar A, Zhao W, Klumpp-Thomas C, Michael S, Covey J, Moore WJ, Stott GM, Li Z, Simeonov A, Jadhav A, Frye S, Hall MD, Shen M, Wang X, Patnaik S, Boxer MB..  (2021)  Discovery and Optimization of 2H-1λ²-Pyridin-2-one Inhibitors of Mutant Isocitrate Dehydrogenase 1 for the Treatment of Cancer.,  64  (8.0): [PMID:33822623] [10.1021/acs.jmedchem.1c00019]

Source

Source(1):

• Scientific Literature