3-(4-(1H-indazol-4-ylamino)pyrimidin-2-ylamino)benzamide

ID: ALA251549

PubChem CID: 24896610

Max Phase: Preclinical

Molecular Formula: C18H15N7O

Molecular Weight: 345.37

Molecule Type: Small molecule

Names and Identifiers

Synonyms: GW782612X | GW782612X|CHEMBL251549|SCHEMBL1172536|2,4-dianilino pyrimidine, 36|BDBM26179|HMS3303M24|HMS3305J04|NSC756345|NSC-756345|NCGC00242231-01|AB01092271-01|3-{[4-(1H-indazol-4-ylamino)pyrimidin-2-yl]amino}benzamide

Canonical SMILES:  NC(=O)c1cccc(Nc2nccc(Nc3cccc4[nH]ncc34)n2)c1

Standard InChI:  InChI=1S/C18H15N7O/c19-17(26)11-3-1-4-12(9-11)22-18-20-8-7-16(24-18)23-14-5-2-6-15-13(14)10-21-25-15/h1-10H,(H2,19,26)(H,21,25)(H2,20,22,23,24)

Standard InChI Key:  NQHLFCVNEBJHOT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   -3.1513    2.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4368    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4368    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7224    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7224    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0079    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2934    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4210    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1355    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8500    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0079    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 16 24  2  0
 20 24  1  0
 14 25  2  0
 10 25  1  0
  8 26  2  0
  4 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA251549

   GW782612X

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: 345.37

Molecular Weight (Monoisotopic): 345.1338

AlogP: 2.94

#Rotatable Bonds: 5

Polar Surface Area: 121.61

Molecular Species: NEUTRAL

HBA: 6

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.81

CX Basic pKa: 4.40

CX LogP: 2.38

CX LogD: 2.38

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.44

Np Likeness Score: -1.82

References

1. Bamborough P, Angell RM, Bhamra I, Brown D, Bull J, Christopher JA, Cooper AW, Fazal LH, Giordano I, Hind L, Patel VK, Ranshaw LE, Sims MJ, Skone PA, Smith KJ, Vickerstaff E, Washington M..  (2007)  N-4-Pyrimidinyl-1H-indazol-4-amine inhibitors of Lck: indazoles as phenol isosteres with improved pharmacokinetics.,  17  (15): [PMID:17600705] [10.1016/j.bmcl.2007.04.029]

2. Compounds: GSK PKIS; Assays: Nanosyn kinase panel,  [10.6019/CHEMBL1961873]

3. Compounds: GSK PKIS; Assays: UNC Frye lab,  [10.6019/CHEMBL2007661]

4. PubChem BioAssay data set, 

5. Data associated with the publication PLoS ONE, 8(3), e57888, (2013) PMID: 23505445. Compounds: GSK PKIS; Assays: NIH NCATS, 

6. Platzer C, Najjar A, Rohe A, Erdmann F, Sippl W, Schmidt M..  (2018)  Identification of PKMYT1 inhibitors by screening the GSK published protein kinase inhibitor set I and II.,  26  (14): [PMID:29941193] [10.1016/j.bmc.2018.06.027]

Source

Source(3):

• Scientific Literature
• PubChem BioAssays
• GSK Published Kinase Inhibitor Set