2-(1-(1-(phenylsulfonyl)-1H-indol-3-yl)hexylidene)hydrazinecarboximidamide

ID: ALA1289118

PubChem CID: 52945065

Max Phase: Preclinical

Molecular Formula: C21H25N5O2S

Molecular Weight: 411.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCC/C(=N\NC(=N)N)c1cn(S(=O)(=O)c2ccccc2)c2ccccc12

Standard InChI:  InChI=1S/C21H25N5O2S/c1-2-3-5-13-19(24-25-21(22)23)18-15-26(20-14-9-8-12-17(18)20)29(27,28)16-10-6-4-7-11-16/h4,6-12,14-15H,2-3,5,13H2,1H3,(H4,22,23,25)/b24-19+

Standard InChI Key:  KVRZUVADWSMEQF-LYBHJNIJSA-N

Molfile:  

     RDKit          2D

 29 31  0  0  0  0  0  0  0  0999 V2000
    9.7736  -15.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7724  -15.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4914  -16.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4896  -14.6705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2008  -15.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2015  -15.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9848  -16.1611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.4667  -15.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9853  -14.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2401  -16.9484    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.0250  -16.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4500  -17.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4917  -17.7333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6352  -17.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4195  -16.9937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5921  -16.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9743  -15.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1924  -15.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2438  -14.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6945  -13.4290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9530  -12.6456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4037  -12.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6622  -11.2465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5960  -12.1979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0515  -13.8767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6008  -14.4923    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4085  -14.3244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9578  -14.9400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7655  -14.7721    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
 19 25  1  0
 10 12  2  0
 25 26  1  0
  2  3  1  0
 26 27  1  0
 10 13  2  0
 27 28  1  0
  3  6  2  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1289118

   2-[(E)-1-[1-(benzenesulfonyl)indol-3-yl]hexylideneamino]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: 411.53

Molecular Weight (Monoisotopic): 411.1729

AlogP: 3.65

#Rotatable Bonds: 8

Polar Surface Area: 113.33

Molecular Species: NEUTRAL

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.93

CX LogP: 3.87

CX LogD: 3.75

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.23

Np Likeness Score: -0.91

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