N-(4-(2-(4-(1H-1,2,3-Triazol-1-yl)phenylamino)pyrimidin-4-yl)-phenyl)methanesulfonamide

ID: ALA571626

PubChem CID: 44627582

Max Phase: Preclinical

Molecular Formula: C19H17N7O2S

Molecular Weight: 407.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)Nc1ccc(-c2ccnc(Nc3ccc(-n4ccnn4)cc3)n2)cc1

Standard InChI:  InChI=1S/C19H17N7O2S/c1-29(27,28)24-16-4-2-14(3-5-16)18-10-11-20-19(23-18)22-15-6-8-17(9-7-15)26-13-12-21-25-26/h2-13,24H,1H3,(H,20,22,23)

Standard InChI Key:  MDCMULVKRBERMG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    2.8141   -6.4762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8141   -7.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287   -7.7184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2476   -7.3059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2476   -6.4762    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287   -6.0591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9615   -7.7193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6767   -7.3078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3874   -7.7253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1019   -7.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1036   -6.4886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3846   -6.0752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6730   -6.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5295   -5.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2450   -4.8248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2442   -4.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5287   -3.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8124   -4.0062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8167   -4.8290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5264   -2.7633    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2397   -2.3488    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.2375   -1.5238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500   -1.9296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6475   -3.0571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8154   -6.0721    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4820   -6.5582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1502   -6.0744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8967   -5.2892    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0717   -5.2879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  4  7  1  0
 14 15  2  0
  1  2  1  0
 15 16  1  0
  7  8  1  0
 16 17  2  0
  1  6  2  0
 17 18  1  0
  8  9  2  0
 18 19  2  0
 19 14  1  0
  6 14  1  0
  2  3  2  0
 17 20  1  0
  9 10  1  0
 20 21  1  0
  3  4  1  0
 21 22  1  0
 10 11  2  0
 21 23  2  0
  4  5  2  0
 21 24  2  0
 25 26  1  0
 11 12  1  0
  5  6  1  0
 12 13  2  0
 13  8  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 25  1  0
 11 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA571626

   N-(4-(2-(4-(1H-1,2,3-Triazol-1-yl)phenylamino)pyrimidin-4-yl)-phenyl)methanesulfonamide

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: 407.46

Molecular Weight (Monoisotopic): 407.1164

AlogP: 2.84

#Rotatable Bonds: 6

Polar Surface Area: 114.69

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.30

CX Basic pKa: 2.46

CX LogP: 2.28

CX LogD: 2.27

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.50

Np Likeness Score: -1.78

References

1. Kamenecka T, Jiang R, Song X, Duckett D, Chen W, Ling YY, Habel J, Laughlin JD, Chambers J, Figuera-Losada M, Cameron MD, Lin L, Ruiz CH, LoGrasso PV..  (2010)  Synthesis, biological evaluation, X-ray structure, and pharmacokinetics of aminopyrimidine c-jun-N-terminal kinase (JNK) inhibitors.,  53  (1): [PMID:19947601] [10.1021/jm901351f]

2. Koch P, Gehringer M, Laufer SA..  (2015)  Inhibitors of c-Jun N-terminal kinases: an update.,  58  (1): [PMID:25415535] [10.1021/jm501212r]

Source

Source(1):

• Scientific Literature