2-ethyl-6-fluoro-4-hydroxy-2H-benzo[b][1,4]oxazin-3(4H)-one

ID: ALA2228069

PubChem CID: 46183606

Max Phase: Preclinical

Molecular Formula: C10H10FNO3

Molecular Weight: 211.19

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCC1Oc2ccc(F)cc2N(O)C1=O

Standard InChI:  InChI=1S/C10H10FNO3/c1-2-8-10(13)12(14)7-5-6(11)3-4-9(7)15-8/h3-5,8,14H,2H2,1H3

Standard InChI Key:  GCHHILUFDJMNNE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
   18.2755   -6.3756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9914   -5.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9914   -5.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2755   -4.7257    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5639   -5.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5639   -5.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8480   -4.7257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1363   -5.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1363   -5.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8480   -6.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7072   -4.7257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4204   -4.7257    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.7072   -6.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4231   -5.9632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2755   -3.9007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  1  6  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  6 10  2  0
  5  7  2  0
  3 11  2  0
  8 12  1  0
 13 14  1  0
  2 13  1  0
  4 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2228069

   6-F-2-Et-D-DIBOA

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: 211.19

Molecular Weight (Monoisotopic): 211.0645

AlogP: 1.72

#Rotatable Bonds: 1

Polar Surface Area: 49.77

Molecular Species: NEUTRAL

HBA: 3

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.76

CX Basic pKa: ┄

CX LogP: 1.63

CX LogD: 1.47

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.72

Np Likeness Score: -0.45

References

1. Macías FA, Chinchilla N, Arroyo E, Molinillo JM, Marín D, Varela RM..  (2010)  Combined strategy for phytotoxicity enhancement of benzoxazinones.,  58  (3): [PMID:20014762] [10.1021/jf903445m]

2. Macías FA, Chinchilla N, Arroyo E, Varela RM, Molinillo JM, Marín D..  (2010)  Multifunctionalised benzoxazinones in the systems Oryza sativa-Echinochloa crus-galli and Triticum aestivum-Avena fatua as natural-product-based herbicide leads.,  66  (10): [PMID:20628996] [10.1002/ps.1992]

Source

Source(1):

• Scientific Literature