methyl 3-oxo-3-(2-(4-sulfamoylphenylamino)-5,6-dihydrobenzo[h]quinazolin-8-ylamino)propanoate

ID: ALA1083483

PubChem CID: 46890287

Max Phase: Preclinical

Molecular Formula: C22H21N5O5S

Molecular Weight: 467.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CC(=O)Nc1ccc2c(c1)CCc1cnc(Nc3ccc(S(N)(=O)=O)cc3)nc1-2

Standard InChI:  InChI=1S/C22H21N5O5S/c1-32-20(29)11-19(28)25-16-6-9-18-13(10-16)2-3-14-12-24-22(27-21(14)18)26-15-4-7-17(8-5-15)33(23,30)31/h4-10,12H,2-3,11H2,1H3,(H,25,28)(H2,23,30,31)(H,24,26,27)

Standard InChI Key:  YLSNDJMDGONFPZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    6.3167  -14.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7333  -15.6375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.1457  -14.9183    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4539  -17.2985    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1703  -16.8852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1675  -16.0547    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4521  -15.6455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4025  -17.2943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4036  -18.1202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3155  -18.5331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0269  -18.1195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8855  -17.2966    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5993  -16.8829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3110  -17.2948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0244  -16.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0235  -16.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3034  -15.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5930  -16.0600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4525  -16.0518    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3118  -16.8831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0275  -17.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7427  -16.8911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7483  -16.0633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0325  -15.6462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3111  -16.0569    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1179  -18.5331    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8326  -18.1210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8330  -17.2960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5468  -18.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2615  -18.1218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2620  -17.2968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9758  -18.5346    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6905  -18.1225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  2  0
 20  8  1  0
 16 17  1  0
  2  1  2  0
 17 18  2  0
 18 13  1  0
 16  2  1  0
  8  9  2  0
  2 19  1  0
 20 21  2  0
  4  5  2  0
  9 10  1  0
  3  2  2  0
 10 11  2  0
 11 21  1  0
  5  6  1  0
 20 25  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  1  0
  5 12  1  0
  9 26  1  0
 26 27  1  0
 12 13  1  0
 27 28  2  0
  6  7  2  0
 27 29  1  0
 13 14  2  0
 29 30  1  0
  7 23  1  0
 30 31  2  0
 14 15  1  0
 30 32  1  0
 22  4  1  0
 32 33  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1083483

   Methyl 3-oxo-3-(2-(4-sulfamoylphenylamino)-5,6-dihydrobenzo[h]quinazolin-8-ylamino)propanoate

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: 467.51

Molecular Weight (Monoisotopic): 467.1263

AlogP: 2.13

#Rotatable Bonds: 6

Polar Surface Area: 153.37

Molecular Species: NEUTRAL

HBA: 8

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.69

CX Basic pKa: 1.65

CX LogP: 2.65

CX LogD: 2.65

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.37

Np Likeness Score: -1.28

References

1. Crombie AL, Sum FW, Powell DW, Hopper DW, Torres N, Berger DM, Zhang Y, Gavriil M, Sadler TM, Arndt K..  (2010)  Synthesis and biological evaluation of tricyclic anilinopyrimidines as IKKbeta inhibitors.,  20  (12): [PMID:20471256] [10.1016/j.bmcl.2010.04.022]

Source

Source(1):

• Scientific Literature