methyl (2-(3-(difluoromethoxy)phenyl)benzo[d]oxazol-5-yl)(ethyl)phosphinate

ID: ALA4798692

PubChem CID: 162675682

Max Phase: Preclinical

Molecular Formula: C17H16F2NO4P

Molecular Weight: 367.29

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H16F2NO4P/c1-3-25(21,22-2)13-7-8-15-14(10-13)20-16(24-15)11-5-4-6-12(9-11)23-17(18)19/h4-10,17H,3H2,1-2H3

Standard InChI Key:  QGRJSFQOKHUSCT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    3.9777  -13.4957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9765  -14.3230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6914  -14.7359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6895  -13.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4049  -13.4920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4097  -14.3185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1972  -14.5692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6791  -13.8978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1894  -13.2321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5021  -13.8924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9183  -14.6061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7424  -14.6015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9076  -13.1778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7304  -13.1698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1475  -13.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2617  -14.7349    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.5476  -14.3219    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2611  -15.5599    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5463  -15.9719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9707  -15.1457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9696  -15.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1377  -12.4523    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9627  -12.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3699  -11.7289    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   10.3803  -13.1578    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
  2 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 16 20  1  0
 20 21  1  0
 14 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4798692

   ---

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: 367.29

Molecular Weight (Monoisotopic): 367.0785

AlogP: 4.67

#Rotatable Bonds: 6

Polar Surface Area: 61.56

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.05

CX LogD: 4.05

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.59

Np Likeness Score: -1.40

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