3-(3-(dimethylamino)phenyl)-6-nitro-2-(piperazin-1-ylmethyl)quinazolin-4(3H)-one

ID: ALA3344453

PubChem CID: 60138205

Max Phase: Preclinical

Molecular Formula: C21H24N6O3

Molecular Weight: 408.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1cccc(-n2c(CN3CCNCC3)nc3ccc([N+](=O)[O-])cc3c2=O)c1

Standard InChI:  InChI=1S/C21H24N6O3/c1-24(2)15-4-3-5-16(12-15)26-20(14-25-10-8-22-9-11-25)23-19-7-6-17(27(29)30)13-18(19)21(26)28/h3-7,12-13,22H,8-11,14H2,1-2H3

Standard InChI Key:  PIQXYALQCZSYKY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    2.0003   -2.8601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9991   -3.6797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7072   -4.0886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7054   -2.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4140   -2.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4174   -3.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1298   -4.0891    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8433   -3.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8400   -2.8507    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1230   -2.4387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1185   -1.6216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5522   -4.0825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5464   -2.4399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5544   -4.8997    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8449   -5.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8451   -6.1192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5521   -6.5297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2605   -6.1204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2619   -5.3006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2918   -2.4519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5842   -2.8607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2916   -1.6348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2546   -2.8484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9606   -2.4383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9585   -1.6202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2445   -1.2140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5415   -1.6264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6693   -2.8450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6715   -3.6622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3760   -2.4346    0.0000 C   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
  5 10  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
  9 13  1  0
 12 14  1  0
 14 15  1  0
 14 19  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 20 21  2  0
 20 22  1  0
  1 20  1  0
 13 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 13  1  0
 24 28  1  0
 28 29  1  0
 28 30  1  0
M  CHG  2  20   1  22  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3344453

   3-[3-(Dimethylamino)phenyl]-6-nitro-2-(piperazin-1-ylmethyl)quinazolin-4-one

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: 408.46

Molecular Weight (Monoisotopic): 408.1910

AlogP: 1.77

#Rotatable Bonds: 5

Polar Surface Area: 96.54

Molecular Species: BASE

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.21

CX LogP: 2.06

CX LogD: 0.26

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.51

Np Likeness Score: -1.83

References

1. Schroeder CE, Yao T, Sotsky J, Smith RA, Roy S, Chu YK, Guo H, Tower NA, Noah JW, McKellip S, Sosa M, Rasmussen L, Smith LH, White EL, Aubé J, Jonsson CB, Chung D, Golden JE..  (2014)  Development of (E)-2-((1,4-dimethylpiperazin-2-ylidene)amino)-5-nitro-N-phenylbenzamide, ML336: Novel 2-amidinophenylbenzamides as potent inhibitors of venezuelan equine encephalitis virus.,  57  (20): [PMID:25244572] [10.1021/jm501203v]

Source

Source(1):

• Scientific Literature