N-[4-[(5,11-dimethyl-6-oxo-pyrimido[4,5-b][1,4]benzodiazepin-2-yl)amino]-3-methoxy-phenyl]methanesulfonamide

ID: ALA4636475

PubChem CID: 134457889

Max Phase: Preclinical

Molecular Formula: C21H22N6O4S

Molecular Weight: 454.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(NS(C)(=O)=O)ccc1Nc1ncc2c(n1)N(C)c1ccccc1C(=O)N2C

Standard InChI:  InChI=1S/C21H22N6O4S/c1-26-16-8-6-5-7-14(16)20(28)27(2)17-12-22-21(24-19(17)26)23-15-10-9-13(11-18(15)31-3)25-32(4,29)30/h5-12,25H,1-4H3,(H,22,23,24)

Standard InChI Key:  ISCJKSNXTHTNBW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    3.2664   -3.8713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8692   -4.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6121   -4.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6121   -3.2703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3546   -4.4613    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9351   -3.8767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5343   -5.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3347   -5.4014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6224   -6.1694    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1029   -6.7975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3168   -7.5961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1152   -7.8099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3304   -8.6092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1301   -8.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7089   -8.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5075   -8.4521    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0879   -7.8674    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.5084   -7.2818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3024   -7.0668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8865   -8.0813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4951   -7.4394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7002   -7.2254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4864   -6.4269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0711   -5.8464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2984   -6.6679    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0091   -5.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1833   -5.8955    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7722   -6.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6772   -5.2444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8855   -5.4786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2862   -4.9116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4784   -4.1097    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  2  0
 17 19  2  0
 17 20  1  0
 15 21  2  0
 21 22  1  0
 22 12  2  0
 22 23  1  0
 23 24  1  0
 25 10  2  0
 26 25  1  0
  7 26  2  0
 27 26  1  0
 27 28  1  0
 29 27  1  0
  2 29  2  0
 29 30  1  0
 31 30  2  0
 32 31  1  0
  1 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4636475

   ---

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: 454.51

Molecular Weight (Monoisotopic): 454.1423

AlogP: 2.96

#Rotatable Bonds: 5

Polar Surface Area: 116.76

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.57

CX Basic pKa: 3.32

CX LogP: 1.62

CX LogD: 1.62

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.60

Np Likeness Score: -1.32

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