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

ID: ALA3819633

PubChem CID: 127051548

Max Phase: Preclinical

Molecular Formula: C28H30N6O3

Molecular Weight: 498.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1ncc2cc(-c3ccc(-n4cccc(C)c4=O)cc3C3CC3)c(=O)n(C[C@@H]3CNCCO3)c2n1

Standard InChI:  InChI=1S/C28H30N6O3/c1-17-4-3-10-33(26(17)35)20-7-8-22(23(13-20)18-5-6-18)24-12-19-14-31-28(29-2)32-25(19)34(27(24)36)16-21-15-30-9-11-37-21/h3-4,7-8,10,12-14,18,21,30H,5-6,9,11,15-16H2,1-2H3,(H,29,31,32)/t21-/m0/s1

Standard InChI Key:  ZTPYVALNBJUYHG-NRFANRHFSA-N

Molfile:  

     RDKit          2D

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   -3.9091    1.5019    0.0000 N   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
   -2.6111   -0.7486    0.0000 N   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 C   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
    3.6321    1.3486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2995    2.9981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6003    3.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6056    5.2467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9072    5.9922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2037    5.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985    3.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8969    2.9922    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.4908   -1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4885   -3.0029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1883   -3.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8904   -2.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7870   -3.7553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7825   -5.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0792   -6.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3805   -5.2634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3852   -3.7634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4263   -3.1666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0885   -3.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0922   -1.8094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1952    0.7498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4489    1.9597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9489    1.9551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 13 12  1  6
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 13 18  1  0
 11 19  1  0
  6 19  1  0
 19 20  2  0
  3 20  1  0
  8 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 21 26  1  0
 24 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 31 33  1  0
 27 33  1  0
 33 34  2  0
 22 35  1  0
 35 36  1  0
 36 37  1  0
 35 37  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3819633

   ---

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: 498.59

Molecular Weight (Monoisotopic): 498.2379

AlogP: 2.83

#Rotatable Bonds: 6

Polar Surface Area: 103.07

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.35

CX LogP: 2.53

CX LogD: 1.54

Aromatic Rings: 4

Heavy Atoms: 37

QED Weighted: 0.42

Np Likeness Score: -0.82

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]

Source

Source(1):

• Scientific Literature