methyl ethyl(2-(2-(trifluoromethyl)pyridin-4-yl)benzo[d]oxazol-5-yl)phosphinate

ID: ALA4793355

PubChem CID: 162673729

Max Phase: Preclinical

Molecular Formula: C16H14F3N2O3P

Molecular Weight: 370.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCP(=O)(OC)c1ccc2oc(-c3ccnc(C(F)(F)F)c3)nc2c1

Standard InChI:  InChI=1S/C16H14F3N2O3P/c1-3-25(22,23-2)11-4-5-13-12(9-11)21-15(24-13)10-6-7-20-14(8-10)16(17,18)19/h4-9H,3H2,1-2H3

Standard InChI Key:  AEHBPIDWECBOEO-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    4.0860  -19.1331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0848  -19.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7997  -20.3733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7979  -18.7203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5132  -19.1294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5181  -19.9559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3056  -20.2067    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7875  -19.5352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2977  -18.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6104  -19.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0266  -20.2435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8508  -20.2390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0159  -18.8153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8388  -18.8072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2559  -19.5217    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3701  -20.3724    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    2.6559  -19.9593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3695  -21.1974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6546  -21.6093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792  -20.7831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0780  -21.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2460  -18.0898    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0710  -18.0838    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.8284  -17.3783    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    9.6541  -17.3706    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
 22 24  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4793355

   ---

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: 370.27

Molecular Weight (Monoisotopic): 370.0694

AlogP: 4.48

#Rotatable Bonds: 4

Polar Surface Area: 65.22

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.42

CX LogD: 3.42

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.63

Np Likeness Score: -1.00

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