(S)-tert-Butyl 3-((2-bromo-5-((2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)methyl)pyridin-3-yl)carbamoyl)pyrrolidine-1-carboxylate

ID: ALA4089975

PubChem CID: 137642588

Max Phase: Preclinical

Molecular Formula: C24H26BrN5O5

Molecular Weight: 544.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)OC(=O)N1CC[C@H](C(=O)Nc2cc(Cn3c(=O)[nH]c(=O)c4ccccc43)cnc2Br)C1

Standard InChI:  InChI=1S/C24H26BrN5O5/c1-24(2,3)35-23(34)29-9-8-15(13-29)20(31)27-17-10-14(11-26-19(17)25)12-30-18-7-5-4-6-16(18)21(32)28-22(30)33/h4-7,10-11,15H,8-9,12-13H2,1-3H3,(H,27,31)(H,28,32,33)/t15-/m0/s1

Standard InChI Key:  BLAGGKQNYDTZSL-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
   14.8745  -13.1081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8787  -13.9253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5843  -13.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8464  -14.6632    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.3007  -15.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5543  -14.9363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6404  -14.1261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4392  -13.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6657  -14.6555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0806  -15.3549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0650  -13.9406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8441  -15.3430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1402  -14.9326    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8420  -16.1602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4280  -16.1607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4301  -15.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7221  -14.9331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0119  -15.3398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0139  -16.1570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7178  -16.5674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1360  -16.5670    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    7.3080  -14.9294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3060  -14.1122    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0162  -13.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0183  -12.8883    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.3102  -12.4778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6001  -12.8846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8962  -12.4742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1860  -12.8851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1839  -13.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8920  -14.1085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6021  -13.7018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3124  -11.6606    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7242  -14.1159    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2980  -14.6313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  4  8  1  0
  9 10  2  0
  9 11  1  0
  4  9  1  0
 12 13  1  0
 12 14  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 15 20  2  0
 15 21  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 23 32  1  0
 27 32  2  0
 26 33  2  0
 24 34  2  0
 22 23  1  0
 18 22  1  0
 13 16  1  0
  6 12  1  1
 11  2  1  0
  2 35  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4089975

   ---

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: 544.41

Molecular Weight (Monoisotopic): 543.1117

AlogP: 3.09

#Rotatable Bonds: 4

Polar Surface Area: 126.39

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.61

CX Basic pKa: 0.48

CX LogP: 2.43

CX LogD: 2.43

Aromatic Rings: 3

Heavy Atoms: 35

QED Weighted: 0.49

Np Likeness Score: -1.50

References

1. Zhao H, Ji M, Cui G, Zhou J, Lai F, Chen X, Xu B..  (2017)  Discovery of novel quinazoline-2,4(1H,3H)-dione derivatives as potent PARP-2 selective inhibitors.,  25  (15): [PMID:28622906] [10.1016/j.bmc.2017.05.052]

Source

Source(1):

• Scientific Literature