(E)-2-(2-chlorostyryl)-4H-benzo[d][1,3]oxazin-4-one

ID: ALA4210978

PubChem CID: 12722020

Max Phase: Preclinical

Molecular Formula: C16H10ClNO2

Molecular Weight: 283.71

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1oc(/C=C/c2ccccc2Cl)nc2ccccc12

Standard InChI:  InChI=1S/C16H10ClNO2/c17-13-7-3-1-5-11(13)9-10-15-18-14-8-4-2-6-12(14)16(19)20-15/h1-10H/b10-9+

Standard InChI Key:  YYDNPZWMYHGIMM-MDZDMXLPSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    4.0226   -9.8393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0215  -10.6588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7295  -11.0678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7277   -9.4304    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4364   -9.8357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4352  -10.6609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1453  -11.0722    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8611  -10.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8623   -9.8377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1476   -9.4218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1477   -8.6046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5677  -11.0735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2765  -10.6669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9831  -11.0775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9758  -11.8957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6815  -12.3062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3913  -11.8996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3910  -11.0782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6847  -10.6713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6838   -9.8542    0.0000 Cl  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  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
  8 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 19 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4210978

   2-[(E)-2-(2-chlorophenyl)ethenyl]-3,1-benzoxazin-4-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: 283.71

Molecular Weight (Monoisotopic): 283.0400

AlogP: 4.01

#Rotatable Bonds: 2

Polar Surface Area: 43.10

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.63

CX LogP: 4.47

CX LogD: 4.47

Aromatic Rings: 3

Heavy Atoms: 20

QED Weighted: 0.71

Np Likeness Score: -0.80

References

1. Goel P, Jumpertz T, Tichá A, Ogorek I, Mikles DC, Hubalek M, Pietrzik CU, Strisovsky K, Schmidt B, Weggen S..  (2018)  Discovery and validation of 2-styryl substituted benzoxazin-4-ones as a novel scaffold for rhomboid protease inhibitors.,  28  (8): [PMID:29463448] [10.1016/j.bmcl.2018.02.017]

Source

Source(1):

• Scientific Literature