4-((6-bromo-4-oxo-2-thioxo-1,2-dihydroquinazolin-3(4H)-yl)methyl)-N-(4-sulfamoylphenethyl)benzamide

ID: ALA520525

PubChem CID: 4650258

Max Phase: Preclinical

Molecular Formula: C24H21BrN4O4S2

Molecular Weight: 573.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)c1ccc(CCNC(=O)c2ccc(Cn3c(=S)[nH]c4ccc(Br)cc4c3=O)cc2)cc1

Standard InChI:  InChI=1S/C24H21BrN4O4S2/c25-18-7-10-21-20(13-18)23(31)29(24(34)28-21)14-16-1-5-17(6-2-16)22(30)27-12-11-15-3-8-19(9-4-15)35(26,32)33/h1-10,13H,11-12,14H2,(H,27,30)(H,28,34)(H2,26,32,33)

Standard InChI Key:  KUYFJJROJAVPPC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
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   11.8417   -1.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5537   -2.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5537   -0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2657   -0.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2622   -1.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9710   -2.2049    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.6878   -1.7977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6913   -0.9727    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9780   -0.5549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9803    0.2701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3999   -2.2142    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.1260   -0.5563    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   15.4079   -0.5640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1202   -0.9802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1137   -1.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8252   -2.2214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5428   -1.8126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5445   -0.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8324   -0.5709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2556   -2.2279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2524   -3.0529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9717   -1.8182    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9750   -0.9932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6910   -0.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6943    0.2415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4138    0.6469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4174    1.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7040    1.8873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9855    1.4731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9855    0.6503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7062    2.7123    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.7000    3.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.5312    2.7143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8812    2.7100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
  5 10  1  0
 17 18  2  0
  6  7  1  0
 18 19  1  0
  7  8  1  0
 19 20  2  0
 20 15  1  0
  8  9  1  0
 18 21  1  0
  9 10  1  0
 21 22  2  0
  5  6  2  0
 21 23  1  0
 10 11  2  0
 23 24  1  0
 24 25  1  0
  8 12  2  0
 25 26  1  0
  1  2  1  0
 26 27  2  0
  1 13  1  0
 27 28  1  0
  1  4  2  0
 28 29  2  0
  9 14  1  0
 29 30  1  0
  2  3  2  0
 30 31  2  0
 31 26  1  0
 14 15  1  0
 29 32  1  0
  3  6  1  0
 32 33  1  0
 15 16  2  0
 32 34  2  0
  5  4  1  0
 32 35  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA520525

   4-[(6-bromo-4-oxo-2-sulfanylidene-1H-quinazolin-3-yl)methyl]-N-[2-(4-sulfamoylphenyl)ethyl]benzamide

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: 573.49

Molecular Weight (Monoisotopic): 572.0188

AlogP: 3.49

#Rotatable Bonds: 7

Polar Surface Area: 127.05

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.98

CX Basic pKa: ┄

CX LogP: 4.70

CX LogD: 4.19

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.29

Np Likeness Score: -1.47

References

1. Yu WM, Guvench O, Mackerell AD, Qu CK..  (2008)  Identification of small molecular weight inhibitors of Src homology 2 domain-containing tyrosine phosphatase 2 (SHP-2) via in silico database screening combined with experimental assay.,  51  (23): [PMID:19007293] [10.1021/jm800229d]

Source

Source(1):

• Scientific Literature