(S)-N-(2-Bromo-5-((2,4-dioxo-3,4-dihydroquinazolin-1(2H)-yl)methyl)phenyl)pyrrolidine-3-carboxamide 2,2,2-trifluoroacetate

ID: ALA4091988

PubChem CID: 137654655

Max Phase: Preclinical

Molecular Formula: C22H20BrF3N4O5

Molecular Weight: 443.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1cc(Cn2c(=O)[nH]c(=O)c3ccccc32)ccc1Br)[C@H]1CCNC1.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C20H19BrN4O3.C2HF3O2/c21-15-6-5-12(9-16(15)23-18(26)13-7-8-22-10-13)11-25-17-4-2-1-3-14(17)19(27)24-20(25)28;3-2(4,5)1(6)7/h1-6,9,13,22H,7-8,10-11H2,(H,23,26)(H,24,27,28);(H,6,7)/t13-;/m0./s1

Standard InChI Key:  HFDNJWSRCJRIEB-ZOWNYOTGSA-N

Molfile:  

     RDKit          2D

 35 37  0  0  0  0  0  0  0  0999 V2000
   12.4353  -11.6223    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.0309  -10.9165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6219  -11.6197    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.7386  -10.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3232  -10.5079    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.4495  -10.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7418   -9.6899    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4614  -13.6726    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9157  -14.2821    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1692  -13.9457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2554  -13.1356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0542  -12.9669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4591  -14.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7552  -13.9421    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4570  -15.1697    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0429  -15.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0451  -14.3530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3370  -13.9425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6269  -14.3493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6289  -15.1665    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3328  -15.5769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9230  -13.9389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9210  -13.1217    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6311  -12.7149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6332  -11.8977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9252  -11.4873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2151  -11.8941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5112  -11.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8010  -11.8945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7989  -12.7117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5069  -13.1180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2171  -12.7112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9273  -10.6701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3391  -13.1253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7494  -15.5809    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  2  4  1  0
  2  5  1  0
  4  6  1  0
  4  7  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  8 12  1  0
 13 14  1  0
 13 15  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 16 21  2  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
 19 22  1  0
 14 17  1  0
 10 13  1  1
 16 35  1  0
M  END

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: 443.30

Molecular Weight (Monoisotopic): 442.0641

AlogP: 2.05

#Rotatable Bonds: 4

Polar Surface Area: 95.99

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.56

CX Basic pKa: 10.55

CX LogP: 1.04

CX LogD: -0.69

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.58

Np Likeness Score: -1.39

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