5-amino-2-(4-nitrophenylamino)benzenesulfonic acid

ID: ALA3087998

Cas Number: 118-87-6

PubChem CID: 76324498

Max Phase: Preclinical

Molecular Formula: C12H11N3O5S

Molecular Weight: 309.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(Nc2ccc([N+](=O)[O-])cc2)c(S(=O)(=O)O)c1

Standard InChI:  InChI=1S/C12H11N3O5S/c13-8-1-6-11(12(7-8)21(18,19)20)14-9-2-4-10(5-3-9)15(16)17/h1-7,14H,13H2,(H,18,19,20)

Standard InChI Key:  OBTPEUAQRSSTFK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   18.2016   -5.7999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9129   -5.3977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6176   -5.8138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6090   -6.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8976   -7.0308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1949   -6.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8910   -7.8480    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.1800   -8.2508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6786   -7.6312    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4681   -8.4237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4841   -7.0214    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7796   -6.6074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7910   -5.7930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0872   -5.3791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3754   -5.7823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3718   -6.6037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0761   -7.0139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6662   -5.3668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9559   -5.7709    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6714   -4.5496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3295   -5.4124    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  1  6  2  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  7 10  2  0
  6 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 18 19  2  0
 18 20  1  0
 15 18  1  0
  3 21  1  0
M  CHG  2  18   1  20  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3087998

   2-(4-Nitrophenylamino)-5-aminobenzenesulfonic acid

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: 309.30

Molecular Weight (Monoisotopic): 309.0419

AlogP: 2.17

#Rotatable Bonds: 4

Polar Surface Area: 135.56

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -3.40

CX Basic pKa: 4.20

CX LogP: 1.48

CX LogD: -0.63

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.34

Np Likeness Score: -1.20

References

1. Iqbal J, Saeed A, Raza R, Matin A, Hameed A, Furtmann N, Lecka J, Sévigny J, Bajorath J..  (2013)  Identification of sulfonic acids as efficient ecto-5'-nucleotidase inhibitors.,  70  [PMID:24215819] [10.1016/j.ejmech.2013.10.053]

Source

Source(1):

• Scientific Literature