N-{5-[2-(N,N-Dimethylsulfamoyl)-4,5-dimethoxy-benzyl]-1,3,4-thiadiazol-2-yl}-N-(p-nitrophenyl)amine

ID: ALA2270956

PubChem CID: 46177119

Max Phase: Preclinical

Molecular Formula: C19H21N5O6S2

Molecular Weight: 479.54

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cc(Cc2nnc(Nc3ccc([N+](=O)[O-])cc3)s2)c(S(=O)(=O)N(C)C)cc1OC

Standard InChI:  InChI=1S/C19H21N5O6S2/c1-23(2)32(27,28)17-11-16(30-4)15(29-3)9-12(17)10-18-21-22-19(31-18)20-13-5-7-14(8-6-13)24(25)26/h5-9,11H,10H2,1-4H3,(H,20,22)

Standard InChI Key:  ZNTYLFGZWVLRPC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
   17.7822   -5.3125    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.5994   -5.3112    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.1897   -4.6041    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.6573   -4.0859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6561   -4.9055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3642   -5.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0738   -4.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0710   -4.0823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3624   -3.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9481   -5.3135    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2407   -4.9043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9495   -3.6775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9493   -2.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7835   -6.1297    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7772   -3.6711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7560   -2.8501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4045   -2.3540    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.1320   -1.5835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3150   -1.6046    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0827   -2.3880    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5905   -0.9082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.4076   -0.8988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8184   -1.6022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6295   -1.5899    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0350   -0.8797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6123   -0.1734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8016   -0.1886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0764   -6.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4918   -6.5371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8500   -0.8669    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2514   -0.1550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2658   -1.5704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  1  3  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  5 10  1  0
 10 11  1  0
  4 12  1  0
 12 13  1  0
  7  1  1  0
  1 14  1  0
  8 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 16  2  0
 18 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
 14 28  1  0
 14 29  1  0
 30 31  2  0
 30 32  1  0
 25 30  1  0
M  CHG  2  30   1  32  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2270956

   4,5-dimethoxy-N,N-dimethyl-2-[[5-(4-nitroanilino)-1,3,4-thiadiazol-2-yl]methyl]benzenesulfonamide

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: 479.54

Molecular Weight (Monoisotopic): 479.0933

AlogP: 3.05

#Rotatable Bonds: 9

Polar Surface Area: 136.79

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.94

CX Basic pKa: 0.58

CX LogP: 2.51

CX LogD: 2.50

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.36

Np Likeness Score: -1.86

References

1. Camoutsis C, Geronikaki A, Ciric A, Soković M, Zoumpoulakis P, Zervou M..  (2010)  Sulfonamide-1,2,4-thiadiazole derivatives as antifungal and antibacterial agents: synthesis, biological evaluation, lipophilicity, and conformational studies.,  58  (2): [PMID:20118573] [10.1248/cpb.58.160]

Source

Source(1):

• Scientific Literature