6-(2-chloro-4-(6-methylpyrazin-2-yl)phenyl)-2-(ethylamino)-8-(3-hydroxypropyl)pyrido[2,3-d]pyrimidin-7(8H)-one

ID: ALA3770806

PubChem CID: 127028469

Max Phase: Preclinical

Molecular Formula: C23H23ClN6O2

Molecular Weight: 450.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNc1ncc2cc(-c3ccc(-c4cncc(C)n4)cc3Cl)c(=O)n(CCCO)c2n1

Standard InChI:  InChI=1S/C23H23ClN6O2/c1-3-26-23-27-12-16-9-18(22(32)30(7-4-8-31)21(16)29-23)17-6-5-15(10-19(17)24)20-13-25-11-14(2)28-20/h5-6,9-13,31H,3-4,7-8H2,1-2H3,(H,26,27,29)

Standard InChI Key:  ICNMDSYSAGMRJC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   -2.6111    0.7486    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
   -1.2964   -1.4973    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
    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
    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
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8926    1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1905    0.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4908    1.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4931    2.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1953    3.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8951    2.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7940    3.7432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0932    2.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3922    3.7432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3922    5.2432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0932    5.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7941    5.2432    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0932    7.1932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8568    3.6007    0.0000 Cl  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
    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
   -3.9091   -1.5019    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9067   -3.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9447   -3.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6034   -5.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6435   -5.8460    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
  9 11  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
 14 17  1  0
 21 23  1  0
 16 24  1  0
  8 25  2  0
  7 26  1  0
 26 27  1  0
  2 28  1  0
 28 29  1  0
 29 30  1  0
 27 31  1  0
 31 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3770806

   ---

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: 450.93

Molecular Weight (Monoisotopic): 450.1571

AlogP: 3.69

#Rotatable Bonds: 7

Polar Surface Area: 105.82

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.72

CX LogP: 2.01

CX LogD: 2.01

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.44

Np Likeness Score: -1.11

References

1. Ndubaku CO, Crawford JJ, Drobnick J, Aliagas I, Campbell D, Dong P, Dornan LM, Duron S, Epler J, Gazzard L, Heise CE, Hoeflich KP, Jakubiak D, La H, Lee W, Lin B, Lyssikatos JP, Maksimoska J, Marmorstein R, Murray LJ, O'Brien T, Oh A, Ramaswamy S, Wang W, Zhao X, Zhong Y, Blackwood E, Rudolph J..  (2015)  Design of Selective PAK1 Inhibitor G-5555: Improving Properties by Employing an Unorthodox Low-pK a Polar Moiety.,  6  (12): [PMID:26713112] [10.1021/acsmedchemlett.5b00398]

Source

Source(1):

• Scientific Literature