6-Hydroxy-N-(4-nitrophenyl)naphthalene-2-carboxamide

ID: ALA3401887

PubChem CID: 118728733

Max Phase: Preclinical

Molecular Formula: C17H12N2O4

Molecular Weight: 308.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(Nc1ccc([N+](=O)[O-])cc1)c1ccc2cc(O)ccc2c1

Standard InChI:  InChI=1S/C17H12N2O4/c20-16-8-3-11-9-13(2-1-12(11)10-16)17(21)18-14-4-6-15(7-5-14)19(22)23/h1-10,20H,(H,18,21)

Standard InChI Key:  TYYMLYFWNLEQSE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6486   -1.3517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8911    1.5017    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8890    3.0026    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9314    0.9035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1872    3.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1872    5.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4863    6.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7853    5.2557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7853    3.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4863    3.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0866    6.0035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1250    5.4020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0887    7.2035    0.0000 O   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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  2 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 21 22  2  0
 21 23  1  0
 18 21  1  0
M  CHG  2  21   1  23  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3401887

   ---

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: 308.29

Molecular Weight (Monoisotopic): 308.0797

AlogP: 3.71

#Rotatable Bonds: 3

Polar Surface Area: 92.47

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.77

CX Basic pKa: ┄

CX LogP: 3.69

CX LogD: 3.69

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.57

Np Likeness Score: -1.00

References

1. Kos J, Nevin E, Soral M, Kushkevych I, Gonec T, Bobal P, Kollar P, Coffey A, O'Mahony J, Liptaj T, Kralova K, Jampilek J..  (2015)  Synthesis and antimycobacterial properties of ring-substituted 6-hydroxynaphthalene-2-carboxanilides.,  23  (9): [PMID:25819330] [10.1016/j.bmc.2015.03.018]

Source

Source(1):

• Scientific Literature