methyl (2-(2-(difluoromethyl)phenyl)benzo[d]oxazol-6-yl)(ethyl)phosphinate

ID: ALA4784420

PubChem CID: 162666581

Max Phase: Preclinical

Molecular Formula: C17H16F2NO3P

Molecular Weight: 351.29

Molecule Type: Unknown

This compound is available for customization.

Associated Items:

Names and Identifiers

Canonical SMILES:  CCP(=O)(OC)c1ccc2nc(-c3ccccc3C(F)F)oc2c1

Standard InChI:  InChI=1S/C17H16F2NO3P/c1-3-24(21,22-2)11-8-9-14-15(10-11)23-17(20-14)13-7-5-4-6-12(13)16(18)19/h4-10,16H,3H2,1-2H3

Standard InChI Key:  CVTHJHJGRMFKLE-UHFFFAOYSA-N

Molfile:  

 
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   15.1934   -9.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.6219   -8.2590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6267   -9.0854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4142   -9.3362    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.8962   -8.6647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4064   -7.9990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.7192   -8.6594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1353   -9.3731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9595   -9.3685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   19.9475   -7.9367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3646   -8.6513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4801   -7.8502    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.4799   -7.0252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7657   -8.2629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0511   -7.8506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4752   -8.6751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7583   -9.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7059   -7.2339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1123   -6.5159    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   17.8810   -7.2409    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

Alternative Forms

  1. Parent:

    ALA4784420

    ---

Associated Targets(Human)

UTRN Tchem Utrophin (89 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: UnknownTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Biocomponents

Calculated Properties

Molecular Weight: 351.29Molecular Weight (Monoisotopic): 351.0836AlogP: 5.00#Rotatable Bonds: 5
Polar Surface Area: 52.33Molecular Species: NEUTRALHBA: 4HBD:
#RO5 Violations: 1HBA (Lipinski): 4HBD (Lipinski): #RO5 Violations (Lipinski): 1
CX Acidic pKa: CX Basic pKa: CX LogP: 3.61CX LogD: 3.61
Aromatic Rings: 3Heavy Atoms: 24QED Weighted: 0.61Np Likeness Score: -1.04

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