4-(5-(4-(5-(2-hydroxyphenyl)-1,3,4-thiadiazol-2-yl)phenyl)-1,3,4-oxadiazol-2-yl)-3-methoxyphenol

ID: ALA4461536

PubChem CID: 155528641

Max Phase: Preclinical

Molecular Formula: C23H16N4O4S

Molecular Weight: 444.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(O)ccc1-c1nnc(-c2ccc(-c3nnc(-c4ccccc4O)s3)cc2)o1

Standard InChI:  InChI=1S/C23H16N4O4S/c1-30-19-12-15(28)10-11-17(19)21-25-24-20(31-21)13-6-8-14(9-7-13)22-26-27-23(32-22)16-4-2-3-5-18(16)29/h2-12,28-29H,1H3

Standard InChI Key:  WTDANXWKZVHJFE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
   33.8625   -9.2780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.8613  -10.0975    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5694  -10.5065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2791  -10.0970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.2762   -9.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5676   -8.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.1533  -10.5055    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.5652   -8.0519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.8562   -7.6454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9802   -8.8648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7279   -9.1943    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   37.2725   -8.5850    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.8612   -7.8787    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.0048   -8.0518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.1876   -7.1329    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0013   -7.0456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3308   -6.2986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8477   -5.6384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.0314   -5.7300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7057   -6.4771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1726   -4.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9710   -4.7176    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   39.0522   -3.9045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   38.3039   -3.5759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7604   -4.1572    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   38.1395   -2.7755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7515   -2.2353    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5875   -1.4355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8114   -1.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1990   -1.7244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3661   -2.5222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.5265   -2.4944    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  6  8  1  0
  8  9  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 10  1  0
  5 10  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 13 15  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 21  1  0
 18 21  1  0
 24 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 26  1  0
 27 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4461536

   ---

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: 444.47

Molecular Weight (Monoisotopic): 444.0892

AlogP: 5.01

#Rotatable Bonds: 5

Polar Surface Area: 114.39

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.29

CX Basic pKa: ┄

CX LogP: 4.06

CX LogD: 4.01

Aromatic Rings: 5

Heavy Atoms: 32

QED Weighted: 0.39

Np Likeness Score: -0.45

References

1. Taha M, Imran S, Alomari M, Rahim F, Wadood A, Mosaddik A, Uddin N, Gollapalli M, Alqahtani MA, Bamarouf YA..  (2019)  Synthesis of oxadiazole-coupled-thiadiazole derivatives as a potent β-glucuronidase inhibitors and their molecular docking study.,  27  (14): [PMID:31196753] [10.1016/j.bmc.2019.05.049]

Source

Source(1):

• Scientific Literature