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

ID: ALA2230188

PubChem CID: 44477647

Max Phase: Preclinical

Molecular Formula: C20H15FN2O6

Molecular Weight: 398.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCOC(=O)CN1C(=O)COc2cc(N3C(=O)c4ccccc4C3=O)c(F)cc21

Standard InChI:  InChI=1S/C20H15FN2O6/c1-2-28-18(25)9-22-15-7-13(21)14(8-16(15)29-10-17(22)24)23-19(26)11-5-3-4-6-12(11)20(23)27/h3-8H,2,9-10H2,1H3

Standard InChI Key:  WEYAWYIZDANBKO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   16.1801  -14.1864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1772  -13.3559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4618  -12.9467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7487  -14.1869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7483  -13.3594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0355  -12.9483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3184  -13.3601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3188  -14.1876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0363  -14.6033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8902  -12.9406    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   16.8953  -14.5978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.9788  -15.4163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6444  -14.2592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1975  -14.8714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7847  -15.5815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1932  -16.2920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0144  -16.2935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4253  -15.5787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0145  -14.8711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8129  -13.4515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.3668  -15.9696    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6042  -12.9470    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.0362  -12.1233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7510  -11.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7518  -10.8863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4652  -12.1245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.1802  -11.7126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8943  -12.1257    0.0000 C   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
  3 11  1  0
  2 12  1  0
 12 13  1  0
 13 16  1  0
 15 14  1  0
 14 12  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 14 21  2  0
 13 22  2  0
  8 23  2  0
  7 24  1  0
 24 25  1  0
 25 26  2  0
 25 27  1  0
 27 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2230188

   Ethyl 2-[7-(1,3-dioxoisoindol-2-yl)-6-fluoro-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: 398.35

Molecular Weight (Monoisotopic): 398.0914

AlogP: 1.91

#Rotatable Bonds: 4

Polar Surface Area: 93.22

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.34

CX LogD: 1.34

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.58

Np Likeness Score: -1.29

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