2-(1-(6-methyl-1-(3-nitrophenylsulfonyl)-1H-indol-3-yl)ethylidene)hydrazinecarboximidamide

ID: ALA1289353

PubChem CID: 52948799

Max Phase: Preclinical

Molecular Formula: C18H18N6O4S

Molecular Weight: 414.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=N\NC(=N)N)c1cn(S(=O)(=O)c2cccc([N+](=O)[O-])c2)c2cc(C)ccc12

Standard InChI:  InChI=1S/C18H18N6O4S/c1-11-6-7-15-16(12(2)21-22-18(19)20)10-23(17(15)8-11)29(27,28)14-5-3-4-13(9-14)24(25)26/h3-10H,1-2H3,(H4,19,20,22)/b21-12+

Standard InChI Key:  QSUCXAHXMDAZLV-CIAFOILYSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
   12.6163  -22.9228    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6152  -23.7461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3343  -24.1590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3325  -22.5100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0437  -22.9192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0443  -23.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8278  -24.0007    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.3098  -23.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8283  -22.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0831  -24.7881    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   15.8681  -24.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2930  -25.0397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3347  -25.5731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.4784  -25.0873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2626  -24.8334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4352  -24.0255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8174  -23.4722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0355  -23.7291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0867  -21.8840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5375  -21.2684    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7959  -20.4849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.2467  -19.8693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5051  -19.0857    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4388  -20.0372    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9009  -24.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8752  -25.3860    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.6633  -25.1314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7060  -26.1925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8946  -21.7161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 11 14  2  0
  1  2  2  0
 14 15  1  0
  5  4  2  0
 15 16  2  0
  6  7  1  0
 16 17  1  0
  7  8  1  0
 17 18  2  0
 18 11  1  0
  8  9  2  0
  9 19  1  0
  9  5  1  0
 19 20  2  0
  4  1  1  0
 20 21  1  0
  7 10  1  0
 21 22  1  0
  5  6  1  0
 22 23  2  0
 10 11  1  0
 22 24  1  0
  2 25  1  0
 10 12  2  0
 15 26  1  0
  2  3  1  0
 10 13  2  0
 26 27  2  0
 26 28  1  0
  3  6  2  0
 19 29  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA1289353

   2-[(E)-1-[6-methyl-1-(3-nitrophenyl)sulfonylindol-3-yl]ethylideneamino]guanidine

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: 414.45

Molecular Weight (Monoisotopic): 414.1110

AlogP: 2.30

#Rotatable Bonds: 5

Polar Surface Area: 156.47

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.26

CX LogP: 2.29

CX LogD: 2.26

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.25

Np Likeness Score: -1.66

References

1. Xu H, Wang YY..  (2010)  Antifungal agents. Part 5: synthesis and antifungal activities of aminoguanidine derivatives of N-arylsulfonyl-3-acylindoles.,  20  (24): [PMID:21067926] [10.1016/j.bmcl.2010.10.084]

Source

Source(1):

• Scientific Literature