Methyl (2-(2-(difluoromethyl)-4-fluorophenyl)benzo[d]oxazol-5-yl)(ethyl)phosphinate

ID: ALA4791949

PubChem CID: 162672118

Max Phase: Preclinical

Molecular Formula: C17H15F3NO3P

Molecular Weight: 369.28

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCP(=O)(OC)c1ccc2oc(-c3ccc(F)cc3C(F)F)nc2c1

Standard InChI:  InChI=1S/C17H15F3NO3P/c1-3-25(22,23-2)11-5-7-15-14(9-11)21-17(24-15)12-6-4-10(18)8-13(12)16(19)20/h4-9,16H,3H2,1-2H3

Standard InChI Key:  JGKUQHWBZKYFRA-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   13.1108   -2.2534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1096   -3.0730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8177   -3.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8159   -1.8446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5245   -2.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5293   -3.0684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3093   -3.3169    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7867   -2.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3016   -1.9924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4016   -3.4810    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.6942   -3.0718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4010   -4.2982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6929   -4.7062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9760   -4.0571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7634   -4.8461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6019   -2.6464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0141   -3.3534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8305   -3.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2357   -2.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8186   -1.9307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0035   -1.9386    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5888   -1.2344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9913   -0.5232    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.7717   -1.2415    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.0529   -2.6324    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
 21 22  1  0
 22 23  1  0
 22 24  1  0
 19 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4791949

   ---

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: 369.28

Molecular Weight (Monoisotopic): 369.0742

AlogP: 5.14

#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: 3.75

CX LogD: 3.75

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.58

Np Likeness Score: -1.18

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