methyl 2-(6-(1,3-dioxo-4,5,6,7-tetrahydro-1H-isoindol-2(3H)-yl)-7-fluoro-3-oxo-2H-benzo[b][1,4]oxazin-4(3H)-yl)propanoate

ID: ALA2230192

PubChem CID: 44478361

Max Phase: Preclinical

Molecular Formula: C20H19FN2O6

Molecular Weight: 402.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C(C)N1C(=O)COc2cc(F)c(N3C(=O)C4=C(CCCC4)C3=O)cc21

Standard InChI:  InChI=1S/C20H19FN2O6/c1-10(20(27)28-2)22-15-8-14(13(21)7-16(15)29-9-17(22)24)23-18(25)11-5-3-4-6-12(11)19(23)26/h7-8,10H,3-6,9H2,1-2H3

Standard InChI Key:  XGYCOHMPAGGLKW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   16.7712  -20.0536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4878  -19.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4849  -18.8096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7694  -18.4004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0565  -19.6406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0560  -18.8133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3432  -18.4022    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6262  -18.8140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6266  -19.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3440  -20.0570    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9119  -20.0536    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1978  -18.3944    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   18.2029  -20.0515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.2865  -20.8700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9520  -19.7129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5051  -20.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0923  -21.0352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5008  -21.7456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3219  -21.7473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7329  -21.0324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3220  -20.3248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1206  -18.9052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6744  -21.4234    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3456  -20.8820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6318  -21.2960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6334  -22.1210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9166  -20.8848    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2028  -21.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0609  -21.2932    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
  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  1  0
 19 20  1  0
 20 21  1  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
 24 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2230192

   Methyl 2-[6-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)-7-fluoro-3-oxo-1,4-benzoxazin-4-yl]propanoate

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: 402.38

Molecular Weight (Monoisotopic): 402.1227

AlogP: 1.86

#Rotatable Bonds: 3

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: 1.03

CX LogP: 1.44

CX LogD: 1.44

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.57

Np Likeness Score: -0.68

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