4-amino-3-hydroxy-7-nitronaphthalene-1-sulfonic acid

ID: ALA3087999

Cas Number: 6259-63-8

PubChem CID: 13742375

Max Phase: Preclinical

Molecular Formula: C10H8N2O6S

Molecular Weight: 284.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1c(O)cc(S(=O)(=O)O)c2cc([N+](=O)[O-])ccc12

Standard InChI:  InChI=1S/C10H8N2O6S/c11-10-6-2-1-5(12(14)15)3-7(6)9(4-8(10)13)19(16,17)18/h1-4,13H,11H2,(H,16,17,18)

Standard InChI Key:  DHXPRBHRJQAXHK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    4.3768   -8.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6623   -8.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479   -8.2386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479   -7.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6623   -7.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6623   -6.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3768   -5.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0913   -6.1761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0913   -7.0011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3768   -7.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0913   -8.6511    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.4448   -9.2920    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5904   -9.2772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7468   -8.2975    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8057   -5.7636    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8057   -4.9386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5202   -6.1761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2334   -8.6511    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2334   -7.0011    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
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  1 10  2  0
  5 10  1  0
 11 12  2  0
 11 13  2  0
 11 14  1  0
  1 11  1  0
 15 16  2  0
 15 17  1  0
  8 15  1  0
  3 18  1  0
  4 19  1  0
M  CHG  2  15   1  17  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3087999

   4-Amino-3-hydroxy-7-nitronaphthalene-1-sulfonic 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: 284.25

Molecular Weight (Monoisotopic): 284.0103

AlogP: 1.28

#Rotatable Bonds: 2

Polar Surface Area: 143.76

Molecular Species: ACID

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: -3.39

CX Basic pKa: 2.16

CX LogP: 0.73

CX LogD: -1.44

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.25

Np Likeness Score: -0.54

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