rac-4-(5-(4-Bromophenyl)-3-(2-oxo-4-phenyl-1,2-dihydroquinolin-3-yl)-4,5-dihydropyrazol-1-yl)-4-oxobutanoic Acid

ID: ALA4475564

PubChem CID: 155537987

Max Phase: Preclinical

Molecular Formula: C28H22BrN3O4

Molecular Weight: 544.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)CCC(=O)N1N=C(c2c(-c3ccccc3)c3ccccc3[nH]c2=O)CC1c1ccc(Br)cc1

Standard InChI:  InChI=1S/C28H22BrN3O4/c29-19-12-10-17(11-13-19)23-16-22(31-32(23)24(33)14-15-25(34)35)27-26(18-6-2-1-3-7-18)20-8-4-5-9-21(20)30-28(27)36/h1-13,23H,14-16H2,(H,30,36)(H,34,35)

Standard InChI Key:  KBWNABXQYOAIMF-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   10.7331  -12.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4450  -13.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4432  -11.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1599  -12.0890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1587  -12.9184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8729  -13.3296    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5929  -12.9204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5940  -12.0910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.8758  -10.8494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5931  -10.4391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5935   -9.6141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8772   -9.1983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1591   -9.6177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1623  -10.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3087  -11.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0627  -12.0169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.3966  -10.8557    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.3074  -13.3331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5408   -9.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3623   -9.8487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0593   -9.2627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4377  -11.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8529  -12.1140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6758  -12.1105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0831  -11.3941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6657  -10.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8441  -10.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6987   -9.0990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5160   -9.0155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8524   -8.2658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9972   -9.6816    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9047  -11.3892    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 11  1  0
 10 11  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 17  2  0
  9 17  1  0
  8 22  2  0
 20 23  1  0
 23 24  1  0
 23 25  2  0
 19 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 24 32  1  0
 32 33  1  0
 33 34  2  0
 33 35  1  0
 29 36  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4475564

   ---

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: 544.41

Molecular Weight (Monoisotopic): 543.0794

AlogP: 5.50

#Rotatable Bonds: 6

Polar Surface Area: 102.83

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: 2

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.85

CX Basic pKa: ┄

CX LogP: 4.91

CX LogD: 1.67

Aromatic Rings: 4

Heavy Atoms: 36

QED Weighted: 0.33

Np Likeness Score: -0.67

References

1. Bagnolini G, Milano D, Manerba M, Schipani F, Ortega JA, Gioia D, Falchi F, Balboni A, Farabegoli F, De Franco F, Robertson J, Pellicciari R, Pallavicini I, Peri S, Minucci S, Girotto S, Di Stefano G, Roberti M, Cavalli A..  (2020)  Synthetic Lethality in Pancreatic Cancer: Discovery of a New RAD51-BRCA2 Small Molecule Disruptor That Inhibits Homologous Recombination and Synergizes with Olaparib.,  63  (5): [PMID:32037829] [10.1021/acs.jmedchem.9b01526]

Source

Source(1):

• Scientific Literature