Methyl ethyl(2-(3-methoxyphenyl)benzo[d]oxazol-5-yl)phosphinate

ID: ALA4762738

PubChem CID: 162660448

Max Phase: Preclinical

Molecular Formula: C17H18NO4P

Molecular Weight: 331.31

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCP(=O)(OC)c1ccc2oc(-c3cccc(OC)c3)nc2c1

Standard InChI:  InChI=1S/C17H18NO4P/c1-4-23(19,21-3)14-8-9-16-15(11-14)18-17(22-16)12-6-5-7-13(10-12)20-2/h5-11H,4H2,1-3H3

Standard InChI Key:  FDJVGIRRTPMYQG-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   12.7352   -8.3741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7341   -9.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4421   -9.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4403   -7.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1489   -8.3705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1537   -9.1891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9338   -9.4376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4111   -8.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9260   -8.1131    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0260   -9.6017    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   11.3186   -9.1925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0254  -10.4189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3174  -10.8269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6004  -10.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3878  -10.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2263   -8.7671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6385   -9.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4549   -9.4696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8601   -8.7589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4430   -8.0513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6279   -8.0593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8449   -7.3398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6620   -7.3321    0.0000 C   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
M  END

Alternative Forms

1. Parent:

   

   ALA4762738

   ---

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: 331.31

Molecular Weight (Monoisotopic): 331.0973

AlogP: 4.07

#Rotatable Bonds: 5

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: 3.20

CX LogD: 3.20

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.66

Np Likeness Score: -0.90

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