8-(((1r,4r)-4-Aminocyclohexyl)methyl)-6-(2-chloro-4-(6-methylpyrazin-2-yl)phenyl)-2-(methylamino)pyrido[2,3-d]pyrimidin-7(8H)-one

ID: ALA3769456

PubChem CID: 117833406

Max Phase: Preclinical

Molecular Formula: C26H28ClN7O

Molecular Weight: 490.01

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1ncc2cc(-c3ccc(-c4cncc(C)n4)cc3Cl)c(=O)n(C[C@H]3CC[C@H](N)CC3)c2n1

Standard InChI:  InChI=1S/C26H28ClN7O/c1-15-11-30-13-23(32-15)17-5-8-20(22(27)10-17)21-9-18-12-31-26(29-2)33-24(18)34(25(21)35)14-16-3-6-19(28)7-4-16/h5,8-13,16,19H,3-4,6-7,14,28H2,1-2H3,(H,29,31,33)/t16-,19-

Standard InChI Key:  HWHNITBPQIFDQC-RUCARUNLSA-N

Molfile:  

     RDKit          2D

 35 39  0  0  0  0  0  0  0  0999 V2000
   -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
    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 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
    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 N   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
   -3.9122    1.4966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9506    0.8952    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
    5.1929   -0.7510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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 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
    7.7825   -5.2553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3852   -3.7634    0.0000 N   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
    9.0792   -6.0094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0755   -7.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1947    0.4490    0.0000 Cl  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
    3.8969    2.9922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1985    3.7378    0.0000 C   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
    3.9072    5.9922    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
    6.2450    5.8341    0.0000 N   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
  1  6  2  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
  3 10  1  0
  4  7  1  0
  9 11  2  0
 12 13  1  0
  1 12  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 14 19  2  0
 20 21  1  0
 20 22  2  0
 21 23  2  0
 23 24  1  0
 24 25  2  0
 22 25  1  0
 25 26  1  0
 17 20  1  0
 15 27  1  0
  8 14  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 29 34  1  0
 32 35  1  1
 29 28  1  6
 10 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3769456

   8-[(4-Aminocyclohexyl)methyl]-6-[2-chloro-4-(6-methylpyrazin-2-yl)phenyl]-2-(methylamino)pyrido[2,3-d]pyrimidin-7-one

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: 490.01

Molecular Weight (Monoisotopic): 489.2044

AlogP: 4.44

#Rotatable Bonds: 5

Polar Surface Area: 111.61

Molecular Species: BASE

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.45

CX LogP: 2.91

CX LogD: 0.16

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.43

Np Likeness Score: -1.03

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