N-[4-[(5,11-dimethyl-6-oxo-pyrimido[4,5-b][1,4]benzodiazepin-2-yl)amino]phenyl]methanesulfonamide

ID: ALA4646447

PubChem CID: 118687444

Max Phase: Preclinical

Molecular Formula: C20H20N6O3S

Molecular Weight: 424.49

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CN1C(=O)c2ccccc2N(C)c2nc(Nc3ccc(NS(C)(=O)=O)cc3)ncc21

Standard InChI:  InChI=1S/C20H20N6O3S/c1-25-16-7-5-4-6-15(16)19(27)26(2)17-12-21-20(23-18(17)25)22-13-8-10-14(11-9-13)24-30(3,28)29/h4-12,24H,1-3H3,(H,21,22,23)

Standard InChI Key:  CAIZEMRPVOVGGT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
   18.7786  -12.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3795  -13.5617    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1245  -13.2178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1245  -12.3898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8689  -13.5816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.4519  -12.9986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0440  -14.3865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8504  -14.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1372  -15.2888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.6192  -15.9193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8325  -16.7196    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.6287  -16.9328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8431  -17.7339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6446  -17.9404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2219  -17.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0222  -17.5731    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.6052  -16.9901    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.4056  -17.2034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8189  -16.1877    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.0231  -16.4021    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.0085  -16.5634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2119  -16.3459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8087  -15.7900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5245  -15.0157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6969  -15.0157    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2829  -15.7317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1881  -14.3664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3987  -14.5999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7970  -14.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9886  -13.2310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  9  8  2  0
 10  9  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 16 15  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 17 20  2  0
 15 21  2  0
 21 22  1  0
 22 12  2  0
 23 10  2  0
 24 23  1  0
  7 24  2  0
 25 24  1  0
 25 26  1  0
 27 25  1  0
  2 27  2  0
 27 28  1  0
 29 28  2  0
 30 29  1  0
  1 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4646447

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 424.49

Molecular Weight (Monoisotopic): 424.1318

AlogP: 2.95

#Rotatable Bonds: 4

Polar Surface Area: 107.53

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.13

CX Basic pKa: 3.82

CX LogP: 1.78

CX LogD: 1.78

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.66

Np Likeness Score: -1.20

References

1. Ferguson FM, Liu Y, Harshbarger W, Huang L, Wang J, Deng X, Capuzzi SJ, Muratov EN, Tropsha A, Muthuswamy S, Westover KD, Gray NS..  (2020)  Synthesis and Structure-Activity Relationships of DCLK1 Kinase Inhibitors Based on a 5,11-Dihydro-6H-benzo[e]pyrimido[5,4-b][1,4]diazepin-6-one Scaffold.,  63  (14): [PMID:32530623] [10.1021/acs.jmedchem.0c00596]

Source

Source(1):

• Scientific Literature