methyl ethyl(2-(2-(trifluoromethyl)pyridin-3-yl)benzo[d]oxazol-6-yl)phosphinate

ID: ALA4757304

PubChem CID: 162656787

Max Phase: Preclinical

Molecular Formula: C16H14F3N2O3P

Molecular Weight: 370.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCP(=O)(OC)c1ccc2nc(-c3cccnc3C(F)(F)F)oc2c1

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

Standard InChI Key:  DJQMKZAWNJQRPL-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   25.7165   -2.9501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7154   -3.7775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4302   -4.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.4284   -2.5373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1439   -2.9464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.1487   -3.7730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9362   -4.0238    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.4182   -3.3523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.9284   -2.6866    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.2413   -3.3469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6573   -4.0606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4816   -4.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6467   -2.6322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4696   -2.6243    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.8867   -3.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.0019   -2.5377    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   25.0017   -1.7127    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2875   -2.9505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5729   -2.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9971   -3.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2803   -3.7710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2280   -1.9214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6343   -1.2033    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.4030   -1.9285    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   28.8099   -1.2043    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
  1 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 16 20  1  0
 20 21  1  0
 13 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4757304

   ---

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: 1.12

CX LogP: 3.42

CX LogD: 3.42

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.63

Np Likeness Score: -1.12

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