US8481536, 479::US8481536, 607

ID: ALA3651236

PubChem CID: 11517029

Max Phase: Preclinical

Molecular Formula: C22H20ClN5O

Molecular Weight: 405.89

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1cc(-c2cc(O)ccc2Cl)cc2nnc(Nc3cccc(N(C)C)c3)nc12

Standard InChI:  InChI=1S/C22H20ClN5O/c1-13-9-14(18-12-17(29)7-8-19(18)23)10-20-21(13)25-22(27-26-20)24-15-5-4-6-16(11-15)28(2)3/h4-12,29H,1-3H3,(H,24,25,27)

Standard InChI Key:  MZDZFBRVVPRKIT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -1.0519   -5.3877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0156   -5.9927    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0218   -7.1927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2883   -5.2495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5847   -6.0040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8864   -5.2585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8915   -3.7585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5951   -3.0039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5973   -1.5031    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8971   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981   -2.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1968    1.5003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4948    0.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7950    1.4963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8333    0.8946    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7974    2.9963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4995    3.7483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1993    3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1610    3.6021    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2935   -3.7495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  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  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 13  1  0
 19 20  2  0
 20 10  1  0
 15 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 25  2  0
 25 26  1  0
 26 27  2  0
 27 21  1  0
 27 28  1  0
  8 29  2  0
 29  4  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3651236

   4-Chloro-3-[3-[3-(dimethylamino)anilino]-5-methyl-1,2,4-benzotriazin-7-yl]phenol

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: 405.89

Molecular Weight (Monoisotopic): 405.1356

AlogP: 5.17

#Rotatable Bonds: 4

Polar Surface Area: 74.17

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.85

CX Basic pKa: 4.87

CX LogP: 5.52

CX LogD: 5.50

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: -1.12

References

1.  (2013)  Benzotriazine inhibitors of kinases, 

2.  (2008)  Benzotriazine inhibitors of kinases, 

Source

Source(2):

• BindingDB Database
• Patent Bioactivity Data