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

ID: ALA1093891

PubChem CID: 46885956

Max Phase: Preclinical

Molecular Formula: C21H17Cl2N3O2S

Molecular Weight: 446.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Clc1cccc(Cl)c1Cc1nnc(Nc2ccc(COCc3ccsc3)cc2)o1

Standard InChI:  InChI=1S/C21H17Cl2N3O2S/c22-18-2-1-3-19(23)17(18)10-20-25-26-21(28-20)24-16-6-4-14(5-7-16)11-27-12-15-8-9-29-13-15/h1-9,13H,10-12H2,(H,24,26)

Standard InChI Key:  RSPHNRQRYLOPNU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.6808  -23.9742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9375  -24.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7666  -24.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0240  -23.9737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7461  -23.5745    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7614  -22.7497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4859  -22.3536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5015  -21.5295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7943  -21.1029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0699  -21.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0577  -22.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9631  -23.5663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9581  -22.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6700  -22.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6654  -21.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9479  -21.0952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2335  -21.5165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2417  -22.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5318  -22.7597    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.3860  -22.7382    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.8086  -20.2781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5301  -19.8780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5443  -19.0531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2658  -18.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0116  -18.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5742  -18.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1740  -17.6720    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.3643  -17.8297    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:

   

   ALA1093891

   5-[(2,6-dichlorophenyl)methyl]-N-[4-(3-thienylmethoxymethyl)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: 446.36

Molecular Weight (Monoisotopic): 445.0419

AlogP: 6.49

#Rotatable Bonds: 8

Polar Surface Area: 60.18

Molecular Species: NEUTRAL

HBA: 6

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: 5.63

CX LogD: 5.60

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.34

Np Likeness Score: -1.89

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