2-hydroxy-N-(4-methyl-2-nitrophenyl)benzamide

ID: ALA499800

PubChem CID: 3605484

Max Phase: Preclinical

Molecular Formula: C14H12N2O4

Molecular Weight: 272.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(NC(=O)c2ccccc2O)c([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C14H12N2O4/c1-9-6-7-11(12(8-9)16(19)20)15-14(18)10-4-2-3-5-13(10)17/h2-8,17H,1H3,(H,15,18)

Standard InChI Key:  KDOKBPOUYXKMPH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 20 21  0  0  0  0  0  0  0  0999 V2000
    0.8738    1.9205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8725    1.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5855    0.6799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3048    1.0934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3017    1.9244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5835    2.3332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0197    0.6816    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0205   -0.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7352   -0.5553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3063   -0.5566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7334   -1.3807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4474   -1.7924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1625   -1.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1590   -0.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4444   -0.1420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4408    0.6830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0157    2.3434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0115    3.1684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7321    1.9344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1591    2.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 10  2  0
  2  3  1  0
  9 11  2  0
  5  6  2  0
 11 12  1  0
  6  1  1  0
 12 13  2  0
  1  2  2  0
 13 14  1  0
  4  7  1  0
 14 15  2  0
 15  9  1  0
  3  4  2  0
 15 16  1  0
  7  8  1  0
  8  9  1  0
 17 18  2  0
 17 19  1  0
  5 17  1  0
  4  5  1  0
  1 20  1  0
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA499800

   2-hydroxy-N-(4-methyl-2-nitrophenyl)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: 272.26

Molecular Weight (Monoisotopic): 272.0797

AlogP: 2.86

#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: 7.18

CX Basic pKa: ┄

CX LogP: 3.21

CX LogD: 2.79

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.66

Np Likeness Score: -1.59

References

1. Coi A, Fiamingo FL, Livi O, Calderone V, Martelli A, Massarelli I, Bianucci AM..  (2009)  QSAR studies on BK channel activators.,  17  (1): [PMID:19026552] [10.1016/j.bmc.2008.10.068]

2. Kirby RW, Martelli A, Calderone V, McKay NG, Lawson K..  (2013)  Large conductance Ca(2+)-activated K(+) channel (BKCa) activating properties of a series of novel N-arylbenzamides: Channel subunit dependent effects.,  21  (14): [PMID:23707646] [10.1016/j.bmc.2013.05.003]

Source

Source(1):

• Scientific Literature