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

ID: ALA3344452

PubChem CID: 57339123

Max Phase: Preclinical

Molecular Formula: C20H21N5O4

Molecular Weight: 395.42

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1-n1c(CN2CCNCC2)nc2ccc([N+](=O)[O-])cc2c1=O

Standard InChI:  InChI=1S/C20H21N5O4/c1-29-18-5-3-2-4-17(18)24-19(13-23-10-8-21-9-11-23)22-16-7-6-14(25(27)28)12-15(16)20(24)26/h2-7,12,21H,8-11,13H2,1H3

Standard InChI Key:  STJZRZWTUNIPRV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   16.4084  -17.4210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4073  -18.2405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1153  -18.6495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1136  -17.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8222  -17.4174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8256  -18.2426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5379  -18.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2515  -18.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2481  -17.4115    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5312  -16.9996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5267  -16.1824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9546  -17.0008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9625  -19.4606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.2530  -19.8664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2533  -20.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9603  -21.0905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6687  -20.6812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6701  -19.8614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6999  -17.0128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.9923  -17.4216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6997  -16.1956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.6628  -17.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3687  -16.9991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3666  -16.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6527  -15.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9497  -16.1873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6640  -18.2264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.9570  -18.6361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3724  -18.6339    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 28  1  0
  9 12  1  0
 28 13  1  0
 13 14  1  0
 13 18  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 19 20  2  0
 19 21  1  0
  1 19  1  0
 12 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 12  1  0
 22 27  1  0
 27 29  1  0
M  CHG  2  19   1  21  -1
M  END

Alternative Forms

1. Parent:

   

   ALA3344452

   3-(2-Methoxyphenyl)-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: 395.42

Molecular Weight (Monoisotopic): 395.1594

AlogP: 1.71

#Rotatable Bonds: 5

Polar Surface Area: 102.53

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: 1.79

CX LogD: -0.01

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.52

Np Likeness Score: -1.59

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