4-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one

ID: ALA2253470

Cas Number: 771-26-6

PubChem CID: 69865

Max Phase: Preclinical

Molecular Formula: C8H7NO3

Molecular Weight: 165.15

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1COc2ccccc2N1O

Standard InChI:  InChI=1S/C8H7NO3/c10-8-5-12-7-4-2-1-3-6(7)9(8)11/h1-4,11H,5H2

Standard InChI Key:  PTSQWRVYIPQDJA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 12 13  0  0  0  0  0  0  0  0999 V2000
   25.1994  -10.5244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1983  -11.3439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9063  -11.7529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9046  -10.1155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6132  -10.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6120  -11.3460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3221  -11.7573    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.0379  -11.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0391  -10.5228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3245  -10.1069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.7445  -11.7586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3198  -12.5745    0.0000 O   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
M  END

Alternative Forms

1. Parent:

   

   ALA2253470

   4-Hydroxy-2H-1,4-benzoxazin-3(4H)-one

Molecule Features

Natural Product: Yes

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: 165.15

Molecular Weight (Monoisotopic): 165.0426

AlogP: 0.80

#Rotatable Bonds: ┄

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: 8.25

CX Basic pKa: ┄

CX LogP: 0.39

CX LogD: 0.34

Aromatic Rings: 1

Heavy Atoms: 12

QED Weighted: 0.58

Np Likeness Score: -0.19

References

1. Macías FA, Chinchilla N, Varela RM, Molinillo JM, Marín D, De Siqueira JM..  (2008)  Modified benzoxazinones in the system Oryza sativa-Echinochloa crus-galli: an approach to the development of biorational herbicide models.,  56  (21): [PMID:18922010] [10.1021/jf802735m]

2. 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]

3. 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]

4. 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