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

ID: ALA4797008

PubChem CID: 162675936

Max Phase: Preclinical

Molecular Formula: C17H15F3NO3P

Molecular Weight: 369.28

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCP(=O)(OC)c1ccc2nc(-c3ccc(F)cc3C(F)F)oc2c1

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

Standard InChI Key:  CYXSRULTMQSCOR-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   21.7903  -20.1326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7892  -20.9521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4972  -21.3611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4955  -19.7237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2041  -20.1290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2089  -20.9476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9889  -21.1960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4663  -20.5309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9812  -19.8715    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2815  -20.5256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6936  -21.2325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5100  -21.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9153  -20.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4981  -19.8098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6831  -19.8178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.2684  -19.1136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6708  -18.4024    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   24.4512  -19.1207    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.7324  -20.5115    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   21.0825  -19.7242    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.0823  -18.9070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3749  -20.1329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6671  -19.7245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0778  -20.5412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3677  -20.9457    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
  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 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  8 10  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 13 19  1  0
  1 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 20 24  1  0
 24 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4797008

   ---

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: -1.24

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