ethyl 2-(7-fluoro-6-(5-nitro-1,3-dioxoisoindolin-2-yl)-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)acetate

ID: ALA2230187

PubChem CID: 44477646

Max Phase: Preclinical

Molecular Formula: C20H14FN3O8

Molecular Weight: 443.34

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)CN1C(=O)COc2cc(F)c(N3C(=O)c4ccc([N+](=O)[O-])cc4C3=O)cc21

Standard InChI:  InChI=1S/C20H14FN3O8/c1-2-31-18(26)8-22-15-7-14(13(21)6-16(15)32-9-17(22)25)23-19(27)11-4-3-10(24(29)30)5-12(11)20(23)28/h3-7H,2,8-9H2,1H3

Standard InChI Key:  GTVXXMLJRHAZLB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    5.7833  -13.9658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4998  -13.5524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4970  -12.7218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7815  -12.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0685  -13.5529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0681  -12.7255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3552  -12.3144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6382  -12.7262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6386  -13.5536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3560  -13.9693    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9239  -13.9658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2098  -12.3067    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.2149  -13.9638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2984  -14.7822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9640  -13.6251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5172  -14.2373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1043  -14.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5128  -15.6578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3339  -15.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7449  -14.9446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3340  -14.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1326  -12.8175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6865  -15.3356    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3576  -14.7943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6438  -15.2082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6455  -16.0332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9286  -14.7970    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2149  -15.2109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4996  -14.7997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5720  -14.9404    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9830  -14.2250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9860  -15.6540    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  3 12  1  0
  2 13  1  0
 13 14  1  0
 14 17  1  0
 16 15  1  0
 15 13  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 15 22  2  0
 14 23  2  0
 10 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
 30 31  2  0
 30 32  1  0
 20 30  1  0
M  CHG  2  30   1  32  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2230187

   Ethyl 2-[7-fluoro-6-(5-nitro-1,3-dioxoisoindol-2-yl)-3-oxo-1,4-benzoxazin-4-yl]acetate

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: 443.34

Molecular Weight (Monoisotopic): 443.0765

AlogP: 1.82

#Rotatable Bonds: 5

Polar Surface Area: 136.36

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.28

CX LogD: 1.28

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.30

Np Likeness Score: -1.57

References

1. Huang MZ, Luo FX, Mo HB, Ren YG, Wang XG, Ou XM, Lei MX, Liu AP, Huang L, Xu MC..  (2009)  Synthesis and herbicidal activity of isoindoline-1,3-dione substituted benzoxazinone derivatives containing a carboxylic ester group.,  57  (20): [PMID:19772294] [10.1021/jf901897f]

Source

Source(1):

• Scientific Literature