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)acetate

ID: ALA2230191

PubChem CID: 44477650

Max Phase: Preclinical

Molecular Formula: C19H17FN2O6

Molecular Weight: 388.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)CN1C(=O)COc2cc(F)c(N3C(=O)C4=C(CCCC4)C3=O)cc21

Standard InChI:  InChI=1S/C19H17FN2O6/c1-27-17(24)8-21-14-7-13(12(20)6-15(14)28-9-16(21)23)22-18(25)10-4-2-3-5-11(10)19(22)26/h6-7H,2-5,8-9H2,1H3

Standard InChI Key:  FXFRPXZBEBMUSK-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    6.3709  -19.5119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3680  -18.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6526  -18.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9395  -19.5124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9391  -18.6849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2263  -18.2737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5092  -18.6856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5096  -19.5131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2271  -19.9288    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7949  -19.9252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0810  -18.2661    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.0861  -19.9233    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1696  -20.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8352  -19.5847    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3883  -20.1968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9755  -20.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3840  -21.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2052  -21.6190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6162  -20.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2053  -20.1966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0038  -18.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5576  -21.2951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2286  -20.7538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5149  -21.1677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5164  -21.9928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7995  -20.7566    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0858  -21.1704    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
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 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
M  END

Alternative Forms

1. Parent:

   

   ALA2230191

   Methyl 2-[6-(1,3-dioxo-4,5,6,7-tetrahydroisoindol-2-yl)-7-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: 388.35

Molecular Weight (Monoisotopic): 388.1071

AlogP: 1.47

#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: 0.87

CX LogD: 0.87

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.58

Np Likeness Score: -0.95

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