3-methoxy-4-(5-(4-(5-(2-nitrophenyl)-1,3,4-thiadiazol-2-yl)phenyl)-1,3,4-oxadiazol-2-yl)phenol

ID: ALA4553860

PubChem CID: 155555883

Max Phase: Preclinical

Molecular Formula: C23H15N5O5S

Molecular Weight: 473.47

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1cc(O)ccc1-c1nnc(-c2ccc(-c3nnc(-c4ccccc4[N+](=O)[O-])s3)cc2)o1

Standard InChI:  InChI=1S/C23H15N5O5S/c1-32-19-12-15(29)10-11-17(19)21-25-24-20(33-21)13-6-8-14(9-7-13)22-26-27-23(34-22)16-4-2-3-5-18(16)28(30)31/h2-12,29H,1H3

Standard InChI Key:  KGHPBTOLPOGTTK-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 34 38  0  0  0  0  0  0  0  0999 V2000
   11.0265  -22.7781    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0254  -23.5977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7334  -24.0066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4431  -23.5972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4403  -22.7745    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7316  -22.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3174  -24.0057    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7292  -21.5521    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0203  -21.1456    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1442  -22.3649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8920  -22.6945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.4365  -22.0851    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.0252  -21.3789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1688  -21.5519    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.3517  -20.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1653  -20.5457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.3366  -18.3918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1351  -18.2178    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2163  -17.4046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.4680  -17.0761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9244  -17.6574    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.3035  -16.2756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9155  -15.7354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7516  -14.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9754  -14.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3630  -15.2245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5301  -16.0223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6917  -15.9959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3037  -15.4543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8548  -16.7966    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
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 13 14  1  0
 14 10  1  0
  5 10  1  0
 15 16  2  0
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 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
 32 33  2  0
 32 34  1  0
 27 32  1  0
M  CHG  2  32   1  34  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4553860

   ---

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: 473.47

Molecular Weight (Monoisotopic): 473.0794

AlogP: 5.21

#Rotatable Bonds: 6

Polar Surface Area: 137.30

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 10

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.53

CX Basic pKa: ┄

CX LogP: 4.31

CX LogD: 4.28

Aromatic Rings: 5

Heavy Atoms: 34

QED Weighted: 0.26

Np Likeness Score: -0.83

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