1-(4-Chlorobenzyl)-6-nitro-2-phenyl-1H-indol-4-ol

ID: ALA1819314

PubChem CID: 54770929

Max Phase: Preclinical

Molecular Formula: C21H15ClN2O3

Molecular Weight: 378.82

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cc(O)c2cc(-c3ccccc3)n(Cc3ccc(Cl)cc3)c2c1

Standard InChI:  InChI=1S/C21H15ClN2O3/c22-16-8-6-14(7-9-16)13-23-19(15-4-2-1-3-5-15)12-18-20(23)10-17(24(26)27)11-21(18)25/h1-12,25H,13H2

Standard InChI Key:  ONMLWUPTHSNGMA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   -2.6716  -17.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6725  -18.0023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9583  -18.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9598  -16.7644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2451  -17.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2409  -17.9979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4547  -18.2489    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0271  -17.5786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4615  -16.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8493  -17.5740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2649  -18.2879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0891  -18.2840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4987  -17.5669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0781  -16.8523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2553  -16.8597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9617  -15.9394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3876  -18.4136    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1014  -17.9999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3890  -19.2386    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1957  -19.0322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7444  -19.6479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5693  -19.6420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9834  -20.3546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5726  -21.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7433  -21.0704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3329  -20.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9858  -21.7851    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  3  6  2  0
 13 14  1  0
  1  2  2  0
 14 15  2  0
 15 10  1  0
  8 10  1  0
  5  4  2  0
  4 16  1  0
  6  7  1  0
  2 17  1  0
  7  8  1  0
 17 18  1  0
  8  9  2  0
 17 19  2  0
  9  5  1  0
  7 20  1  0
  4  1  1  0
 20 21  1  0
  5  6  1  0
 21 22  2  0
 10 11  2  0
 22 23  1  0
 23 24  2  0
 11 12  1  0
 24 25  1  0
  2  3  1  0
 25 26  2  0
 26 21  1  0
 12 13  2  0
 24 27  1  0
M  CHG  2  17   1  18  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1819314

   1-[(4-Chlorophenyl)methyl]-6-nitro-2-phenylindol-4-ol

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: 378.82

Molecular Weight (Monoisotopic): 378.0771

AlogP: 5.62

#Rotatable Bonds: 4

Polar Surface Area: 68.30

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 7.48

CX Basic pKa: ┄

CX LogP: 5.83

CX LogD: 5.57

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.37

Np Likeness Score: -0.98

References

1. Kokurkina GV, Dutov MD, Shevelev SA, Popkov SV, Zakharov AV, Poroikov VV..  (2011)  Synthesis, antifungal activity and QSAR study of 2-arylhydroxynitroindoles.,  46  (9): [PMID:21802177] [10.1016/j.ejmech.2011.07.008]

Source

Source(1):

• Scientific Literature