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

ID: ALA2228074

PubChem CID: 46183610

Max Phase: Preclinical

Molecular Formula: C10H10ClNO3

Molecular Weight: 227.65

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H10ClNO3/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:  XQGOTDCLNUXWBR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 16  0  0  0  0  0  0  0  0999 V2000
   25.9887  -11.9280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.7059  -11.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7059  -10.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9887  -10.2763    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.2757  -10.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2757  -11.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5627  -10.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8496  -10.6913    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8496  -11.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5627  -11.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4230  -10.2763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.4230  -11.9280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1361  -11.5172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1325  -10.2763    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   25.9887   -9.4505    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
 12 13  1  0
  2 12  1  0
  8 14  1  0
  4 15  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2228074

   6-Cl-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: 227.65

Molecular Weight (Monoisotopic): 227.0349

AlogP: 2.23

#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: 7.86

CX Basic pKa: ┄

CX LogP: 2.09

CX LogD: 1.96

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.75

Np Likeness Score: -0.26

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