2-(3,5-Dinitrophenyl)-5-((3-(morpholine-4-yl)propyl)sulfanyl)-1,3,4-oxadiazole

ID: ALA4094514

PubChem CID: 137655208

Max Phase: Preclinical

Molecular Formula: C15H17N5O6S

Molecular Weight: 395.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cc(-c2nnc(SCCCN3CCOCC3)o2)cc([N+](=O)[O-])c1

Standard InChI:  InChI=1S/C15H17N5O6S/c21-19(22)12-8-11(9-13(10-12)20(23)24)14-16-17-15(26-14)27-7-1-2-18-3-5-25-6-4-18/h8-10H,1-7H2

Standard InChI Key:  UVSBGFZPFIMBHL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   26.1101   -9.2045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.6955   -9.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.1004  -10.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9197  -10.6265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3324   -9.9149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9252   -9.2074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8783   -9.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3370   -8.4950    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.9301   -7.7863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.1542   -8.4969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3279  -11.3366    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.1451  -11.3397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.9166  -12.0427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4071   -9.2435    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.6284   -9.4913    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.6233  -10.3085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.3990  -10.5657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9593  -10.7848    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.2148  -10.4479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5508  -10.9241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8063  -10.5872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1422  -11.0635    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4008  -10.7242    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7385  -11.1968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8148  -12.0108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5593  -12.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2276  -11.8750    0.0000 C   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
  8  9  2  0
  8 10  1  0
  6  8  1  0
 11 12  2  0
 11 13  1  0
  4 11  1  0
  7 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17  7  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 27  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
M  CHG  4   8   1  10  -1  11   1  13  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4094514

   ---

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: 395.40

Molecular Weight (Monoisotopic): 395.0900

AlogP: 2.37

#Rotatable Bonds: 8

Polar Surface Area: 137.67

Molecular Species: NEUTRAL

HBA: 10

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 6.65

CX LogP: 1.93

CX LogD: 1.86

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.28

Np Likeness Score: -2.12

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