(S*)-6-(2-Chloro-4-(3-methyl-2-oxopyridin-1(2H)-yl)phenyl)-8-(2-hydroxyethyl)-2-(methylamino)pyrido[2,3-d]pyrimidin-7(8H)-one

ID: ALA3818479

PubChem CID: 127052178

Max Phase: Preclinical

Molecular Formula: C27H26ClF2N7O3

Molecular Weight: 570.00

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1nccn(-c2ccc(-c3cc4cnc(NC5COC5)nc4n(CC4CCNCC4(F)F)c3=O)c(Cl)c2)c1=O

Standard InChI:  InChI=1S/C27H26ClF2N7O3/c1-15-24(38)36(7-6-32-15)19-2-3-20(22(28)9-19)21-8-16-10-33-26(34-18-12-40-13-18)35-23(16)37(25(21)39)11-17-4-5-31-14-27(17,29)30/h2-3,6-10,17-18,31H,4-5,11-14H2,1H3,(H,33,34,35)

Standard InChI Key:  SNHDCUDTVCJVGD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 40 45  0  0  0  0  0  0  0  0999 V2000
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   -9.0788    6.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3817    5.2926    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3893    3.7926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0941    3.0360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7912    3.7793    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7836    5.2794    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7414    5.8741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4965    3.0203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1925    3.7616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8985    3.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086    1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2125    0.7617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2206   -0.4383    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -6.5065    1.5203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911   -1.5017    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890   -3.0026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9461   -4.0152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8817   -5.0722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8248   -4.0078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2907   -2.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5870   -3.7544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8880   -3.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1852   -3.7608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1815   -5.2608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8807   -6.0076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5835   -5.2544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5602   -4.6276    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6087   -6.4542    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6486   -1.3517    0.0000 O   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
  5  6  1  0
  6  7  1  0
  2  7  1  0
  7  8  2  0
  6  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  9 15  1  0
 12 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 23 26  1  0
 21 27  1  0
 27 28  2  0
 18 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 31 36  1  0
 36 37  1  0
 36 38  1  0
 29 39  1  0
 16 39  1  0
 39 40  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3818479

   ---

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: 570.00

Molecular Weight (Monoisotopic): 569.1754

AlogP: 3.02

#Rotatable Bonds: 6

Polar Surface Area: 115.96

Molecular Species: NEUTRAL

HBA: 10

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.39

CX Basic pKa: 7.09

CX LogP: 2.49

CX LogD: 2.31

Aromatic Rings: 4

Heavy Atoms: 40

QED Weighted: 0.36

Np Likeness Score: -0.93

References

1. Rudolph J, Murray LJ, Ndubaku CO, O'Brien T, Blackwood E, Wang W, Aliagas I, Gazzard L, Crawford JJ, Drobnick J, Lee W, Zhao X, Hoeflich KP, Favor DA, Dong P, Zhang H, Heise CE, Oh A, Ong CC, La H, Chakravarty P, Chan C, Jakubiak D, Epler J, Ramaswamy S, Vega R, Cain G, Diaz D, Zhong Y..  (2016)  Chemically Diverse Group I p21-Activated Kinase (PAK) Inhibitors Impart Acute Cardiovascular Toxicity with a Narrow Therapeutic Window.,  59  (11): [PMID:27167326] [10.1021/acs.jmedchem.6b00638]

2. Rudolph J, Murray LJ, Ndubaku CO, O'Brien T, Blackwood E, Wang W, Aliagas I, Gazzard L, Crawford JJ, Drobnick J, Lee W, Zhao X, Hoeflich KP, Favor DA, Dong P, Zhang H, Heise CE, Oh A, Ong CC, La H, Chakravarty P, Chan C, Jakubiak D, Epler J, Ramaswamy S, Vega R, Cain G, Diaz D, Zhong Y..  (2016)  Chemically Diverse Group I p21-Activated Kinase (PAK) Inhibitors Impart Acute Cardiovascular Toxicity with a Narrow Therapeutic Window.,  59  (11): [PMID:27167326] [10.1021/acs.jmedchem.6b00638]

Source

Source(1):

• Scientific Literature