2-Hydroxy-5-(4-((4-sulfamoylphenyl)amino)phthalazin-1-yl)benzenesulfonamide

ID: ALA5198760

PubChem CID: 168286409

Max Phase: Preclinical

Molecular Formula: C20H17N5O5S2

Molecular Weight: 471.52

Names and Identifiers

Canonical SMILES:  NS(=O)(=O)c1ccc(Nc2nnc(-c3ccc(O)c(S(N)(=O)=O)c3)c3ccccc23)cc1

Standard InChI:  InChI=1S/C20H17N5O5S2/c21-31(27,28)14-8-6-13(7-9-14)23-20-16-4-2-1-3-15(16)19(24-25-20)12-5-10-17(26)18(11-12)32(22,29)30/h1-11,26H,(H,23,25)(H2,21,27,28)(H2,22,29,30)

Standard InChI Key:  NJMQOVFETYTCRE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    0.2401    4.0121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6520    3.2973    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.0647    4.0121    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3654    2.8854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0613    2.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0613    2.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7730    1.6485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857    2.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4857    2.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7720    3.2939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7720    4.1178    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7730    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4845    0.4145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4845   -0.4093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7680   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7680   -1.6465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0545   -2.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0545   -2.8857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6608   -3.2933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3698   -2.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0833   -3.2940    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.4960   -2.5810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9087   -3.2940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0833   -4.1178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3698   -2.0580    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6590   -1.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0575   -0.4067    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0575    0.4128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1935   -0.8204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9087   -0.4130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9087    0.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1953    0.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  2  3  2  0
  2  4  1  0
  5  2  1  0
  6  5  2  0
  7  6  1  0
  8  7  2  0
  9  8  1  0
 10  9  2  0
  5 10  1  0
 10 11  1  0
 12  7  1  0
 13 12  1  0
 14 13  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  2  0
 21 24  1  0
 20 25  2  0
 25 26  1  0
 26 17  2  0
 15 27  2  0
 27 28  1  0
 28 12  2  0
 29 14  1  0
 30 29  2  0
 31 30  1  0
 32 31  2  0
 13 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5198760

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 471.52

Molecular Weight (Monoisotopic): 471.0671

AlogP: 2.04

#Rotatable Bonds: 5

Polar Surface Area: 178.36

Molecular Species: NEUTRAL

HBA: 8

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 6.71

CX Basic pKa: 2.99

CX LogP: 1.74

CX LogD: 0.99

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.34

Np Likeness Score: -1.26

References

1. Lee SY, Namasivayam V, Boshta NM, Perotti A, Mirza S, Bua S, Supuran CT, Müller CE..  (2021)  Discovery of potent nucleotide pyrophosphatase/phosphodiesterase3 (NPP3) inhibitors with ancillary carbonic anhydrase inhibition for cancer (immuno)therapy.,  12  (7.0): [PMID:34355184] [10.1039/D1MD00117E]

2. Ahmad, Haseen and 7 more authors.  2020-12-15  Synthesis of biphenyl oxazole derivatives via Suzuki coupling and biological evaluations as nucleotide pyrophosphatase/phosphodiesterase-1 and -3 inhibitors.  [PMID:32883636]

Source

Source(1):

• Scientific Literature