5-isopropyl-2-[2-methoxy-4-(4-methylpiperazin-1-yl)anilino]-11-methyl-pyrimido[4,5-b][1,4]benzodiazepin-6-one

ID: ALA4649318

PubChem CID: 134457684

Max Phase: Preclinical

Molecular Formula: C27H33N7O2

Molecular Weight: 487.61

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(N2CCN(C)CC2)ccc1Nc1ncc2c(n1)N(C)c1ccccc1C(=O)N2C(C)C

Standard InChI:  InChI=1S/C27H33N7O2/c1-18(2)34-23-17-28-27(30-25(23)32(4)22-9-7-6-8-20(22)26(34)35)29-21-11-10-19(16-24(21)36-5)33-14-12-31(3)13-15-33/h6-11,16-18H,12-15H2,1-5H3,(H,28,29,30)

Standard InChI Key:  CYUJWTUNNJDJKV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   19.5653  -13.6008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9803  -14.1858    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2373  -13.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2373  -12.9940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4941  -14.1658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8909  -13.5912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1025  -13.8340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9102  -14.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   17.8124  -15.6208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3970  -16.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6346  -15.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9240  -16.3895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.7289  -16.5233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   22.3365  -17.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1355  -18.1746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.3495  -18.9736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1442  -19.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7292  -18.6025    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.5282  -18.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5152  -17.8037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7163  -17.5897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1224  -17.1655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3272  -16.9472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1133  -16.1525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6982  -15.5674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2487  -15.8949    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9651  -15.1264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1559  -14.9894    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3601  -13.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  1  0
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  6 11  2  0
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 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 22  1  0
 21 29  2  0
 29 30  1  0
 30 18  2  0
 30 31  1  0
 31 32  1  0
 16 33  1  0
 33 34  2  0
 35 34  1  0
  3 35  1  0
 35 14  2  0
  2 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4649318

   ---

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: 487.61

Molecular Weight (Monoisotopic): 487.2696

AlogP: 4.12

#Rotatable Bonds: 5

Polar Surface Area: 77.07

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.84

CX LogP: 3.98

CX LogD: 3.40

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.58

Np Likeness Score: -1.31

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