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

ID: ALA2269106

Cas Number: 55574-10-2

PubChem CID: 150658

Max Phase: Preclinical

Molecular Formula: C9H9NO4

Molecular Weight: 195.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1Oc2ccccc2N(O)C1=O

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

Standard InChI Key:  YOZATHXJJPZWLM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 14 15  0  0  0  0  0  0  0  0999 V2000
    1.9433   -7.1168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9422   -7.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6566   -8.3564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6548   -6.7043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3697   -7.1132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3685   -7.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0850   -8.3608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8074   -7.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8086   -7.1152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0874   -6.6956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5202   -8.3621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5236   -6.7048    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0827   -9.1854    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5257   -5.8802    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
  9 12  1  0
  7 13  1  0
 12 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2269106

   4-Hydroxy-2-methoxy-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: 195.17

Molecular Weight (Monoisotopic): 195.0532

AlogP: 0.77

#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: 7.90

CX Basic pKa: ┄

CX LogP: 0.75

CX LogD: 0.63

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.67

Np Likeness Score: 0.90

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. 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