methyl 4-hydroxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-carboxylate

ID: ALA2269104

PubChem CID: 15111929

Max Phase: Preclinical

Molecular Formula: C10H9NO5

Molecular Weight: 223.18

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1ccc2c(c1)OCC(=O)N2O

Standard InChI:  InChI=1S/C10H9NO5/c1-15-10(13)6-2-3-7-8(4-6)16-5-9(12)11(7)14/h2-4,14H,5H2,1H3

Standard InChI Key:  ZMWNJEMHNHRWBY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 17  0  0  0  0  0  0  0  0999 V2000
   27.2982   -2.9749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2970   -3.8022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0118   -4.2151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0100   -2.5621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7254   -2.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7242   -3.8044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4410   -4.2196    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.1638   -3.8064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1649   -2.9734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.4435   -2.5535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.8770   -4.2209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.4387   -5.0446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.5836   -2.5626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5834   -1.7376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.8693   -2.9752    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.1547   -2.5629    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  2  0
 13 15  1  0
 15 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2269104

   7-MeOCO-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: 223.18

Molecular Weight (Monoisotopic): 223.0481

AlogP: 0.59

#Rotatable Bonds: 1

Polar Surface Area: 76.07

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 7.94

CX Basic pKa: ┄

CX LogP: 0.40

CX LogD: 0.28

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.56

Np Likeness Score: -0.27

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