methyl (2-(2-(difluoromethoxy)pyridin-4-yl)benzo[d]oxazol-6-yl)(ethyl)phosphinate

ID: ALA4761507

PubChem CID: 162660745

Max Phase: Preclinical

Molecular Formula: C16H15F2N2O4P

Molecular Weight: 368.28

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCP(=O)(OC)c1ccc2nc(-c3ccnc(OC(F)F)c3)oc2c1

Standard InChI:  InChI=1S/C16H15F2N2O4P/c1-3-25(21,22-2)11-4-5-12-13(9-11)23-15(20-12)10-6-7-19-14(8-10)24-16(17)18/h4-9,16H,3H2,1-2H3

Standard InChI Key:  VPTBLQYXMUAFAT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   32.5748   -8.0068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5737   -8.8263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2817   -9.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2799   -7.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9885   -8.0032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9933   -8.8218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7734   -9.0702    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.2507   -8.4051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7656   -7.7457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0659   -8.3998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4781   -9.1067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2945   -9.1023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.4675   -7.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8670   -7.5984    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   31.8668   -6.7812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.1594   -8.0071    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.4516   -7.5987    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8622   -8.4154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1521   -8.8199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2826   -7.6840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6958   -8.3918    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.6860   -6.9733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   38.5032   -6.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9066   -6.2567    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   38.9169   -7.6721    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 21  2  0
 20 13  2  0
 13 10  1  0
  8 10  1  0
  1 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 14 18  1  0
 18 19  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4761507

   ---

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: 368.28

Molecular Weight (Monoisotopic): 368.0738

AlogP: 4.06

#Rotatable Bonds: 6

Polar Surface Area: 74.45

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.16

CX LogP: 3.44

CX LogD: 3.44

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: -1.31

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