6-(4-methoxyphenyl)-7,9-dimethyl-7H-5,7,9,11a-tetraaza-benzo[a]fluorene-8,10-dione

ID: ALA1277052

PubChem CID: 1086999

Max Phase: Preclinical

Molecular Formula: C22H18N4O3

Molecular Weight: 386.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(-c2nc3ccccc3n3cc4c(=O)n(C)c(=O)n(C)c4c23)cc1

Standard InChI:  InChI=1S/C22H18N4O3/c1-24-19-15(21(27)25(2)22(24)28)12-26-17-7-5-4-6-16(17)23-18(20(19)26)13-8-10-14(29-3)11-9-13/h4-12H,1-3H3

Standard InChI Key:  UGTLTFJXHCGKQH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    7.6277  -16.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6266  -17.1357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3414  -17.5485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3396  -15.8955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0550  -16.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0557  -17.1315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4813  -16.2977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7654  -15.8905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4861  -17.1277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7717  -17.5430    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9459  -18.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1018  -17.6788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7673  -18.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2503  -19.0957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0700  -19.0107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4045  -18.2568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9192  -17.5879    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.1932  -15.8809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9075  -16.2925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6190  -15.8763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6144  -15.0505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8924  -14.6425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1839  -15.0610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3258  -14.6327    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0433  -15.0399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5549  -19.6782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9146  -19.8493    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2528  -16.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2250  -18.1703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6 10  1  0
  3  6  2  0
  9  7  1  0
  1  2  2  0
 12 17  1  0
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 15 16  1  0
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  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
 21 24  1  0
 11 13  2  0
 24 25  1  0
 12  9  2  0
 15 26  1  0
 12 13  1  0
 14 27  2  0
  2  3  1  0
 17 28  1  0
  5  6  1  0
 16 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1277052

   6-(4-methoxyphenyl)-7,9-dimethylpyrimido[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: 386.41

Molecular Weight (Monoisotopic): 386.1379

AlogP: 2.71

#Rotatable Bonds: 2

Polar Surface Area: 70.53

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 2.53

CX LogD: 2.53

Aromatic Rings: 5

Heavy Atoms: 29

QED Weighted: 0.47

Np Likeness Score: -0.77

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