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

ID: ALA4792580

PubChem CID: 162671580

Max Phase: Preclinical

Molecular Formula: C17H16F2NO4P

Molecular Weight: 367.29

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCP(=O)(OC)c1ccc2oc(-c3ccccc3OC(F)F)nc2c1

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

Standard InChI Key:  FXPCLIZBZBIFNC-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   12.3638  -14.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3626  -14.8232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0707  -15.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0689  -13.5948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7775  -14.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7823  -14.8187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5623  -15.0671    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.0397  -14.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5546  -13.7426    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6546  -15.2312    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   10.9472  -14.8221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6539  -16.0484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.9459  -16.4564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2290  -15.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0163  -16.5963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8549  -14.3967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2670  -15.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0835  -15.0991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4887  -14.3885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0715  -13.6809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2565  -13.6888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8418  -12.9847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2443  -12.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8296  -11.5693    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.0614  -12.2664    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
 23 24  1  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4792580

   ---

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: -1.25

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