3-(4-(3H-benzo[d][1,2,3]triazol-5-ylamino)pyrimidin-2-ylamino)benzamide

ID: ALA250542

PubChem CID: 25138039

Max Phase: Preclinical

Molecular Formula: C17H14N8O

Molecular Weight: 346.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1cccc(Nc2nccc(Nc3ccc4nn[nH]c4c3)n2)c1

Standard InChI:  InChI=1S/C17H14N8O/c18-16(26)10-2-1-3-11(8-10)21-17-19-7-6-15(22-17)20-12-4-5-13-14(9-12)24-25-23-13/h1-9H,(H2,18,26)(H,23,24,25)(H2,19,20,21,22)

Standard InChI Key:  XLAULLDWFHUVHP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 29  0  0  0  0  0  0  0  0999 V2000
   -5.1434   -9.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1446  -10.6822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4297  -11.0951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7132  -10.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7161   -9.8512    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4315   -9.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0031   -9.4359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2871   -9.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2874  -10.6685    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5721  -11.0782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8582  -10.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8640   -9.8337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5797   -9.4276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5694  -11.9033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8536  -12.3134    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8543  -13.1395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1393  -13.5496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1461  -11.8990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4299  -11.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1445  -12.3325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7155  -12.3328    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5695  -12.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5707  -13.1302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556  -13.3840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8395  -12.7158    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3536  -12.0493    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  2  0
 13  8  1  0
  1  2  2  0
 10 14  1  0
  5  7  1  0
 14 15  1  0
  3  4  2  0
 15 16  2  0
  7  8  1  0
 16 17  1  0
 17 23  2  0
 22 18  2  0
 18 15  1  0
  8  9  2  0
  3 19  1  0
  4  5  1  0
 19 20  2  0
  9 10  1  0
 19 21  1  0
 22 23  1  0
  2  3  1  0
 10 11  2  0
  5  6  2  0
 11 12  1  0
  6  1  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA250542

   3-{[4-(1H-1,2,3-benzotriazol-6-ylamino)pyrimidin-2-yl]amino}benzamide

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: 346.35

Molecular Weight (Monoisotopic): 346.1291

AlogP: 2.33

#Rotatable Bonds: 5

Polar Surface Area: 134.50

Molecular Species: NEUTRAL

HBA: 7

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.03

CX Basic pKa: 5.42

CX LogP: 2.38

CX LogD: 2.37

Aromatic Rings: 4

Heavy Atoms: 26

QED Weighted: 0.44

Np Likeness Score: -1.81

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]

Source

Source(1):

• Scientific Literature