Methyl (2-(3-(difluoromethyl)phenyl)benzo[d]oxazol-5-yl)(ethyl)phosphinate

ID: ALA4791999

PubChem CID: 162670692

Max Phase: Preclinical

Molecular Formula: C17H16F2NO3P

Molecular Weight: 351.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCP(=O)(OC)c1ccc2oc(-c3cccc(C(F)F)c3)nc2c1

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

Standard InChI Key:  CVTIBCMNXPQIRG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    3.6233  -20.6693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6221  -21.4966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3369  -21.9094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3351  -20.2566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0504  -20.6656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0553  -21.4921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8427  -21.7428    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3246  -21.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8349  -20.4058    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9074  -21.9085    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.1933  -21.4955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9067  -22.7334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1920  -23.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4873  -22.4901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2725  -23.2865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1475  -21.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5635  -21.7797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3878  -21.7751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7968  -21.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3757  -20.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5529  -20.3515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7814  -19.6251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6063  -19.6174    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.3623  -18.9147    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
  2 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  0
 10 14  1  0
 14 15  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  8 16  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4791999

   ---

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: -1.08

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