methyl (2-(4-(difluoromethyl)phenyl)benzo[d]oxazol-6-yl)(ethyl)phosphinate

ID: ALA4793431

PubChem CID: 162674278

Max Phase: Preclinical

Molecular Formula: C17H16F2NO3P

Molecular Weight: 351.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCP(=O)(OC)c1ccc2nc(-c3ccc(C(F)F)cc3)oc2c1

Standard InChI:  InChI=1S/C17H16F2NO3P/c1-3-24(21,22-2)13-8-9-14-15(10-13)23-17(20-14)12-6-4-11(5-7-12)16(18)19/h4-10,16H,3H2,1-2H3

Standard InChI Key:  JPZUKXHZBAEZPU-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   15.3192  -13.3206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3181  -14.1480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0329  -14.5609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0311  -12.9078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7464  -13.3170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7513  -14.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5388  -14.3943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.0207  -13.7227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5309  -13.0571    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8437  -13.7174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2598  -14.4311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0840  -14.4266    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2491  -13.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0720  -12.9948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4891  -13.7093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6047  -12.9083    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.6045  -12.0833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.8903  -13.3210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1758  -12.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5998  -13.7331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8830  -14.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3140  -13.7035    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7317  -14.4150    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.7215  -12.9861    0.0000 F   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
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
 10 11  2  0
 11 12  1  0
 12 15  2  0
 14 13  2  0
 13 10  1  0
  8 10  1  0
 14 15  1  0
  1 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 16 20  1  0
 20 21  1  0
 15 22  1  0
 22 23  1  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4793431

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 351.29

Molecular Weight (Monoisotopic): 351.0836

AlogP: 5.00

#Rotatable Bonds: 5

Polar Surface Area: 52.33

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.61

CX LogD: 3.61

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.61

Np Likeness Score: -1.04

References

1. Chatzopoulou M,Emer E,Lecci C,Rowley JA,Casagrande AS,Moir L,Squire SE,Davies SG,Harriman S,Wynne GM,Wilson FX,Davies KE,Russell AJ.  (2020)  Decreasing HepG2 Cytotoxicity by Lowering the Lipophilicity of Benzo[d]oxazolephosphinate Ester Utrophin Modulators.,  11  (12): [PMID:33335663] [10.1021/acsmedchemlett.0c00405]

2. Chatzopoulou, Maria and 16 more authors.  2020-03-12  Isolation, Structural Identification, Synthesis, and Pharmacological Profiling of 1,2-trans-Dihydro-1,2-diol Metabolites of the Utrophin Modulator Ezutromid.  [PMID:31599580]

3. Babbs, Arran and 19 more authors.  2020-07-23  2-Arylbenzo[d]oxazole Phosphinate Esters as Second-Generation Modulators of Utrophin for the Treatment of Duchenne Muscular Dystrophy.  [PMID:32551645]

4. Chatzopoulou, Maria and 12 more authors.  2020-12-10  Decreasing HepG2 Cytotoxicity by Lowering the Lipophilicity of Benzo[d]oxazolephosphinate Ester Utrophin Modulators.  [PMID:33335663]

Source

Source(1):

• Scientific Literature