7,9-dimethyl-6-p-tolyl-7H-5,7,9,11a-tetraaza-benzo[a]fluorene-8,10-dione

ID: ALA1277139

PubChem CID: 5059356

Max Phase: Preclinical

Molecular Formula: C22H18N4O2

Molecular Weight: 370.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(-c2nc3ccccc3n3cc4c(=O)n(C)c(=O)n(C)c4c23)cc1

Standard InChI:  InChI=1S/C22H18N4O2/c1-13-8-10-14(11-9-13)18-20-19-15(21(27)25(3)22(28)24(19)2)12-26(20)17-7-5-4-6-16(17)23-18/h4-12H,1-3H3

Standard InChI Key:  QMODGWYRAPYPLM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   15.2902  -16.5958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2891  -17.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0039  -17.8360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0021  -16.1830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7175  -16.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7182  -17.4190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1438  -16.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4279  -16.1780    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1486  -17.4152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4342  -17.8305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6084  -18.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7643  -17.9663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4298  -18.7202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9128  -19.3832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7325  -19.2982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.0670  -18.5443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5817  -17.8754    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.8557  -16.1684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5700  -16.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2815  -16.1638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2769  -15.3380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5549  -14.9300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8464  -15.3485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2174  -19.9657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5772  -20.1368    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9153  -17.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8875  -18.4578    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9883  -14.9202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
  6 10  1  0
  3  6  2  0
  9  7  1  0
  1  2  2  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
  7  8  2  0
  7 18  1  0
  8  5  1  0
 18 19  2  0
  9 10  1  0
 19 20  1  0
  5  4  2  0
 20 21  2  0
  4  1  1  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 10 11  1  0
 15 24  1  0
 11 13  2  0
 14 25  2  0
 12  9  2  0
 17 26  1  0
 12 13  1  0
 16 27  2  0
  2  3  1  0
 21 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1277139

   7,9-dimethyl-6-(4-methylphenyl)pyrimido[4',5':3,4]pyrrolo[1,2-a]quinoxaline-8,10(7H,9H)-dione

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: 370.41

Molecular Weight (Monoisotopic): 370.1430

AlogP: 3.01

#Rotatable Bonds: 1

Polar Surface Area: 61.30

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.20

CX LogD: 3.20

Aromatic Rings: 5

Heavy Atoms: 28

QED Weighted: 0.46

Np Likeness Score: -0.88

References

1. Carosati E, Sforna G, Pippi M, Marverti G, Ligabue A, Guerrieri D, Piras S, Guaitoli G, Luciani R, Costi MP, Cruciani G..  (2010)  Ligand-based virtual screening and ADME-tox guided approach to identify triazolo-quinoxalines as folate cycle inhibitors.,  18  (22): [PMID:20951595] [10.1016/j.bmc.2010.09.065]

Source

Source(1):

• Scientific Literature