5-(2,6-dichlorobenzyl)-N-(4-((furan-3-ylmethoxy)methyl)phenyl)-1,3,4-oxadiazol-2-amine

ID: ALA1093890

PubChem CID: 46885955

Max Phase: Preclinical

Molecular Formula: C21H17Cl2N3O3

Molecular Weight: 430.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Clc1cccc(Cl)c1Cc1nnc(Nc2ccc(COCc3ccoc3)cc2)o1

Standard InChI:  InChI=1S/C21H17Cl2N3O3/c22-18-2-1-3-19(23)17(18)10-20-25-26-21(29-20)24-16-6-4-14(5-7-16)11-28-13-15-8-9-27-12-15/h1-9,12H,10-11,13H2,(H,24,26)

Standard InChI Key:  NOQMIWOFQMNCFA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
   -2.3667  -23.0208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0401  -23.5076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7834  -24.2959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9542  -24.2959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6968  -23.5070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9748  -23.1079    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9594  -22.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2350  -21.8869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2193  -21.0628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9265  -20.6363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6510  -21.0398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6631  -21.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7577  -23.0996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7627  -22.2747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0508  -21.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0555  -21.0376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7730  -20.6286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4873  -21.0498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4791  -21.8727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1890  -22.2930    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.3348  -22.2716    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.9123  -19.8114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1908  -19.4113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1765  -18.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5450  -18.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2908  -18.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8533  -17.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4532  -17.2053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6434  -17.3630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 13 14  1  0
  6  7  1  0
 14 15  2  0
  1  2  1  0
 15 16  1  0
  7  8  2  0
 16 17  2  0
  3  4  1  0
 17 18  1  0
  8  9  1  0
 18 19  2  0
 19 14  1  0
  4  5  2  0
 19 20  1  0
  9 10  2  0
 15 21  1  0
  5  1  1  0
 10 22  1  0
 10 11  1  0
 22 23  1  0
  2  3  2  0
 23 24  1  0
 11 12  2  0
 24 25  1  0
 25 26  1  0
 12  7  1  0
  5  6  1  0
  2 13  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 25  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA1093890

   5-[(2,6-dichlorophenyl)methyl]-N-[4-(3-furylmethoxymethyl)phenyl]-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: 430.29

Molecular Weight (Monoisotopic): 429.0647

AlogP: 6.02

#Rotatable Bonds: 8

Polar Surface Area: 73.32

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.59

CX Basic pKa: ┄

CX LogP: 4.98

CX LogD: 4.96

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.37

Np Likeness Score: -1.14

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