2-((3-(4-Benzylpiperazin-1-yl)propyl)sulfanyl)-5-(3,5-dinitrophenyl)-1,3,4-oxadiazole

ID: ALA4102544

PubChem CID: 137657422

Max Phase: Preclinical

Molecular Formula: C22H24N6O5S

Molecular Weight: 484.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cc(-c2nnc(SCCCN3CCN(Cc4ccccc4)CC3)o2)cc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C22H24N6O5S/c29-27(30)19-13-18(14-20(15-19)28(31)32)21-23-24-22(33-21)34-12-4-7-25-8-10-26(11-9-25)16-17-5-2-1-3-6-17/h1-3,5-6,13-15H,4,7-12,16H2

Standard InChI Key:  DFJYTBUGXQCOGS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   26.5292  -21.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9341  -22.5619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.7534  -22.5666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   27.7503  -23.9828    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   20.9759  -23.0036    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2345  -22.6643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5722  -23.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6485  -23.9509    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3930  -24.2900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0613  -23.8151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9826  -24.4246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2394  -24.0849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1661  -23.2724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4237  -22.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.8373  -24.2241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5799  -24.5601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  3  4  2  0
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  5  6  2  0
  6  1  1  0
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  8  9  2  0
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  6  8  1  0
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  4 11  1  0
  7 14  2  0
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 31 32  2  0
 32 33  1  0
 33 34  2  0
 34 29  1  0
M  CHG  4   8   1  10  -1  11   1  13  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4102544

   ---

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: 484.54

Molecular Weight (Monoisotopic): 484.1529

AlogP: 3.85

#Rotatable Bonds: 10

Polar Surface Area: 131.68

Molecular Species: NEUTRAL

HBA: 10

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.90

CX LogP: 3.72

CX LogD: 3.10

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.18

Np Likeness Score: -1.79

References

1. Roh J, Karabanovich G, Vlčková H, Carazo A, Němeček J, Sychra P, Valášková L, Pavliš O, Stolaříková J, Klimešová V, Vávrová K, Pávek P, Hrabálek A..  (2017)  Development of water-soluble 3,5-dinitrophenyl tetrazole and oxadiazole antitubercular agents.,  25  (20): [PMID:28835350] [10.1016/j.bmc.2017.08.010]

Source

Source(1):

• Scientific Literature