4-hydroxy-7-methoxy-2H-benzo[b][1,4]oxazin-3(4H)-one

ID: ALA2269102

Cas Number: 69884-05-5

PubChem CID: 50919

Max Phase: Preclinical

Molecular Formula: C9H9NO4

Molecular Weight: 195.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)OCC(=O)N2O

Standard InChI:  InChI=1S/C9H9NO4/c1-13-6-2-3-7-8(4-6)14-5-9(11)10(7)12/h2-4,12H,5H2,1H3

Standard InChI Key:  AFMLVQPDSTZQOF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 14 15  0  0  0  0  0  0  0  0999 V2000
   13.9083   -2.3196    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9072   -3.1466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6216   -3.5592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6198   -1.9071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3349   -2.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3337   -3.1487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0502   -3.5638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7725   -3.1508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7737   -2.3181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0526   -1.8984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4855   -3.5651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.0479   -4.3883    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1941   -1.9075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1939   -1.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  5 10  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  8 11  2  0
  7 12  1  0
  1 13  1  0
 13 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2269102

   4-hydroxy-7-methoxy-3,4-dihydro-2H-1,4-benzoxazin-3-one

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: 195.17

Molecular Weight (Monoisotopic): 195.0532

AlogP: 0.81

#Rotatable Bonds: 1

Polar Surface Area: 59.00

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.19

CX Basic pKa: ┄

CX LogP: 0.23

CX LogD: 0.17

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.67

Np Likeness Score: -0.12

References

1. Bravo HR, Copaja SV, Argandoña VH..  (2004)  Chemical basis for the antifeedant activity of natural hydroxamic acids and related compounds.,  52  (9): [PMID:15113164] [10.1021/jf030766t]

2. Macías FA, Chinchilla N, Varela RM, Molinillo JM, Marín D, de Siqueira JM..  (2009)  Aromatic-ring-functionalised benzoxazinones in the system Oryza sativa-Echinochloa crus-galli as biorational herbicide models.,  65  (10): [PMID:19551813] [10.1002/ps.1799]

3. de Bruijn WJC, Hageman JA, Araya-Cloutier C, Gruppen H, Vincken JP..  (2018)  QSAR of 1,4-benzoxazin-3-one antimicrobials and their drug design perspectives.,  26  (23-24): [PMID:30471830] [10.1016/j.bmc.2018.11.016]

Source

Source(1):

• Scientific Literature