N-(4-(benzyloxymethyl)phenyl)-5-(2,6-dichlorobenzyl)-1,3,4-oxadiazol-2-amine

ID: ALA1090928

PubChem CID: 46885890

Max Phase: Preclinical

Molecular Formula: C23H19Cl2N3O2

Molecular Weight: 440.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Clc1cccc(Cl)c1Cc1nnc(Nc2ccc(COCc3ccccc3)cc2)o1

Standard InChI:  InChI=1S/C23H19Cl2N3O2/c24-20-7-4-8-21(25)19(20)13-22-27-28-23(30-22)26-18-11-9-17(10-12-18)15-29-14-16-5-2-1-3-6-16/h1-12H,13-15H2,(H,26,28)

Standard InChI Key:  XCQSLJIWOJKCFZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    6.0666   -3.8083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3933   -4.2951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6500   -5.0834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4791   -5.0834    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7365   -4.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4586   -3.8954    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4739   -3.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1984   -2.6744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2140   -1.8503    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5068   -1.4238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7824   -1.8273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6756   -3.8871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6706   -3.0622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3825   -2.6493    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3779   -1.8251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6604   -1.4161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.9542   -2.6602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2443   -3.0805    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.0985   -3.0591    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.5211   -0.5989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2426   -0.1988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2568    0.6261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9783    1.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6865    0.5986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4075    0.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4222    1.8238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7099    2.2485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9918    1.8466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  6  7  1  0
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  7  8  2  0
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  3  4  1  0
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  8  9  1  0
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  4  5  2  0
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  9 10  2  0
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  5  1  1  0
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  2  3  2  0
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 11 12  2  0
 24 25  1  0
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  5  6  1  0
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  2 13  1  0
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 29 30  2  0
 30 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1090928

   N-[4-(benzyloxymethyl)phenyl]-5-[(2,6-dichlorophenyl)methyl]-1,3,4-oxadiazol-2-amine

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 440.33

Molecular Weight (Monoisotopic): 439.0854

AlogP: 6.43

#Rotatable Bonds: 8

Polar Surface Area: 60.18

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.59

CX Basic pKa: ┄

CX LogP: 5.84

CX LogD: 5.82

Aromatic Rings: 4

Heavy Atoms: 30

QED Weighted: 0.34

Np Likeness Score: -1.28

References

1. Leung CS, Zeevaart JG, Domaoal RA, Bollini M, Thakur VV, Spasov KA, Anderson KS, Jorgensen WL..  (2010)  Eastern extension of azoles as non-nucleoside inhibitors of HIV-1 reverse transcriptase; cyano group alternatives.,  20  (8): [PMID:20304641] [10.1016/j.bmcl.2010.03.006]

Source

Source(1):

• Scientific Literature