methyl ethyl(2-(5-(trifluoromethyl)pyridin-3-yl)benzo[d]oxazol-5-yl)phosphinate

ID: ALA4760298

PubChem CID: 162657905

Max Phase: Preclinical

Molecular Formula: C16H14F3N2O3P

Molecular Weight: 370.27

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCP(=O)(OC)c1ccc2oc(-c3cncc(C(F)(F)F)c3)nc2c1

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

Standard InChI Key:  VPHLZQJGDODHIE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   22.2567   -8.0976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2556   -8.9171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9636   -9.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9618   -7.6887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6705   -8.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.6753   -8.9126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4553   -9.1610    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.9326   -8.4959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4475   -7.8365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5476   -9.3252    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.8402   -8.9160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5469  -10.1423    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8389  -10.5504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1219   -9.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9093  -10.6903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.7478   -8.4906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1600   -9.1975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9764   -9.1931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.3817   -8.4824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9645   -7.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1494   -7.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3664   -7.0633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1836   -7.0556    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   26.9512   -6.3595    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   27.7680   -6.3518    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
 20 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4760298

   ---

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: 2.71

CX LogP: 3.02

CX LogD: 3.02

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.63

Np Likeness Score: -1.20

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