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

ID: ALA451316

Cas Number: 17359-53-4

PubChem CID: 152213

Max Phase: Preclinical

Molecular Formula: C9H9NO4

Molecular Weight: 195.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc2c(c1)OC(O)C(=O)N2

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

Standard InChI Key:  NDEPTLCFICMYLH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 14 15  0  0  0  0  0  0  0  0999 V2000
    3.2777   -3.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2766   -4.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9956   -5.1485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9938   -3.4997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7050   -3.9088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7052   -4.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4207   -5.1465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1340   -3.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4203   -3.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8549   -3.4987    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1333   -4.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8480   -5.1455    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5637   -3.4992    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645   -2.6742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  5  4  2  0
  6  7  1  0
  8  9  1  0
  9  5  1  0
  4  1  1  0
  8 10  1  0
  5  6  1  0
  7 11  1  0
  8 11  1  0
 11 12  2  0
  2  3  1  0
  1 13  1  0
  3  6  2  0
 13 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA451316

   2-Hydroxy-7-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: 0.34

#Rotatable Bonds: 1

Polar Surface Area: 67.79

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.06

CX Basic pKa: ┄

CX LogP: 0.31

CX LogD: 0.31

Aromatic Rings: 1

Heavy Atoms: 14

QED Weighted: 0.68

Np Likeness Score: 0.99

References

1. Otsuka H, Hirai Y, Nagao T, Yamasaki K..  (1988)  Anti-inflammatory activity of benzoxazinoids from roots of Coix lachryma-jobi var. ma-yuen.,  51  (1): [PMID:2453615] [10.1021/np50055a009]

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. 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