2-(1-(1-(4-methoxyphenylsulfonyl)-6-methyl-1H-indol-3-yl)ethylidene)hydrazinecarboximidamide

ID: ALA1289352

PubChem CID: 52947589

Max Phase: Preclinical

Molecular Formula: C19H21N5O3S

Molecular Weight: 399.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)n2cc(/C(C)=N/NC(=N)N)c3ccc(C)cc32)cc1

Standard InChI:  InChI=1S/C19H21N5O3S/c1-12-4-9-16-17(13(2)22-23-19(20)21)11-24(18(16)10-12)28(25,26)15-7-5-14(27-3)6-8-15/h4-11H,1-3H3,(H4,20,21,23)/b22-13+

Standard InChI Key:  MISRQBOQFAMKEU-LPYMAVHISA-N

Molfile:  

     RDKit          2D

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    4.2891  -23.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0081  -24.3194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0063  -22.6705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7175  -23.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7181  -23.9061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5015  -24.1611    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9834  -23.4979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5020  -22.8281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7568  -24.9484    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.5417  -24.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9667  -25.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0083  -25.7333    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.1519  -25.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9361  -24.9937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1087  -24.1859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4909  -23.6326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7091  -23.8895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7604  -22.0446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2112  -21.4290    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4696  -20.6456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9204  -20.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1788  -19.2465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1126  -20.1979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5748  -24.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8932  -23.9303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5067  -24.4819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5682  -21.8767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  6  2  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
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  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
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  5  6  1  0
 22 23  2  0
 10 11  1  0
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  2 25  1  0
 10 12  2  0
 16 26  1  0
  2  3  1  0
 26 27  1  0
 10 13  2  0
 19 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1289352

   2-[(E)-1-[1-(4-methoxyphenyl)sulfonyl-6-methylindol-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: 399.48

Molecular Weight (Monoisotopic): 399.1365

AlogP: 2.40

#Rotatable Bonds: 5

Polar Surface Area: 122.56

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 6.56

CX LogP: 2.20

CX LogD: 2.14

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.35

Np Likeness Score: -1.24

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