8-Carboxy-11H-indeno[2,3-b]quinoxalin-11-one oxime

ID: ALA4553054

PubChem CID: 155555966

Max Phase: Preclinical

Molecular Formula: C16H9N3O3

Molecular Weight: 291.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(O)c1ccc2nc3c(nc2c1)/C(=N\O)c1ccccc1-3

Standard InChI:  InChI=1S/C16H9N3O3/c20-16(21)8-5-6-11-12(7-8)18-15-13(17-11)9-3-1-2-4-10(9)14(15)19-22/h1-7,22H,(H,20,21)/b19-14-

Standard InChI Key:  PYABQVKREKYNJT-RGEXLXHISA-N

Molfile:  

 
     RDKit          2D

 22 25  0  0  0  0  0  0  0  0999 V2000
   25.4883  -21.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4872  -21.8353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1952  -22.2443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1935  -20.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9021  -21.0122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9028  -21.8312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6114  -22.2383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6058  -20.6020    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3149  -21.0053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3225  -21.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1039  -22.0703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.0915  -20.7450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5770  -21.4034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3879  -21.3113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7143  -20.5616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.2238  -19.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4147  -19.9985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.3644  -22.8449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.8239  -23.4577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7792  -22.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0718  -21.8342    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.7785  -23.0606    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 10  2  0
  9  8  2  0
  8  5  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 12  9  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
 11 18  2  0
 18 19  1  0
  2 20  1  0
 20 21  1  0
 20 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4553054

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 291.27

Molecular Weight (Monoisotopic): 291.0644

AlogP: 2.54

#Rotatable Bonds: 1

Polar Surface Area: 95.67

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.63

CX Basic pKa: ┄

CX LogP: 2.87

CX LogD: -0.61

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.41

Np Likeness Score: -0.44

References

1. Schepetkin IA, Khlebnikov AI, Potapov AS, Kovrizhina AR, Matveevskaya VV, Belyanin ML, Atochin DN, Zanoza SO, Gaidarzhy NM, Lyakhov SA, Kirpotina LN, Quinn MT..  (2019)  Synthesis, biological evaluation, and molecular modeling of 11H-indeno[1,2-b]quinoxalin-11-one derivatives and tryptanthrin-6-oxime as c-Jun N-terminal kinase inhibitors.,  161  [PMID:30347329] [10.1016/j.ejmech.2018.10.023]

Source

Source(1):

• Scientific Literature