3-(4-(4-chlorophenyl)thiazol-2-yl)-1-(2,5-dimethoxyphenyl)-7,8-dihydro-1,7-naphthyridine-2,5(1H,6H)-dione

ID: ALA4877853

PubChem CID: 145112347

Max Phase: Preclinical

Molecular Formula: C25H20ClN3O4S

Molecular Weight: 493.97

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccc(OC)c(-n2c3c(cc(-c4nc(-c5ccc(Cl)cc5)cs4)c2=O)C(=O)CNC3)c1

Standard InChI:  InChI=1S/C25H20ClN3O4S/c1-32-16-7-8-23(33-2)20(9-16)29-21-11-27-12-22(30)17(21)10-18(25(29)31)24-28-19(13-34-24)14-3-5-15(26)6-4-14/h3-10,13,27H,11-12H2,1-2H3

Standard InChI Key:  BIDSDGMJTGSMSB-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   22.1273  -18.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1273  -19.4145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.8394  -19.8228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8394  -18.1727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5514  -18.5894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5480  -19.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2568  -19.8278    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9737  -19.4205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9772  -18.5955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2638  -18.1776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8394  -17.3477    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6859  -19.8371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.6908  -18.1836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4428  -18.5230    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9981  -17.9128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5893  -17.1960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7814  -17.3634    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   24.2522  -20.6515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5338  -21.0594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5288  -21.8837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2415  -22.3011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9608  -21.8882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9622  -21.0652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.8175  -18.0019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1483  -18.7591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9676  -18.8498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4570  -18.1845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1212  -17.4261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3029  -17.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8117  -22.2919    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.0997  -21.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6780  -20.6547    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.3913  -21.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2772  -18.2739    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  1  4  1  0
  2  3  1  0
  3  6  1  0
  5  4  1  0
  5  6  2  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
  4 11  2  0
  8 12  2  0
 13 14  2  0
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 15 16  2  0
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 17 13  1  0
  9 13  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
  7 18  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
 15 24  1  0
 20 30  1  0
 30 31  1  0
 23 32  1  0
 32 33  1  0
 27 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4877853

   ---

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: 493.97

Molecular Weight (Monoisotopic): 493.0863

AlogP: 4.58

#Rotatable Bonds: 5

Polar Surface Area: 82.45

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 5.25

CX LogP: 3.87

CX LogD: 3.87

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.44

Np Likeness Score: -0.95

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