3-(3-methylbut-2-en-1-yl)-1,4-dioxo-1,4-dihydronaphthalen-2-yl-4-methylbenzenesulfonate

ID: ALA2023282

PubChem CID: 60143791

Max Phase: Preclinical

Molecular Formula: C22H20O5S

Molecular Weight: 396.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)=CCC1=C(OS(=O)(=O)c2ccc(C)cc2)C(=O)c2ccccc2C1=O

Standard InChI:  InChI=1S/C22H20O5S/c1-14(2)8-13-19-20(23)17-6-4-5-7-18(17)21(24)22(19)27-28(25,26)16-11-9-15(3)10-12-16/h4-12H,13H2,1-3H3

Standard InChI Key:  BEGPCZRXAITNKB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
   -1.2553   -3.7235    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6656   -4.4393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8406   -4.4367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5431   -3.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5443   -4.5648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8294   -4.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8312   -3.3247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1159   -3.7338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1125   -4.5623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6842   -3.7280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4040   -3.3144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4086   -2.4894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6808   -4.5564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3983   -4.9726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3966   -5.7976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9651   -4.9668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9626   -5.7918    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2469   -6.2021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2444   -7.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5337   -5.7874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9710   -3.3133    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5421   -3.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1730   -3.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8857   -3.3074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8836   -2.4816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1628   -2.0714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5469   -2.4878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5962   -2.0659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0
  7  4  1  0
 14 15  2  0
  8  9  1  0
 13 16  1  0
  2  1  2  0
 16 17  1  0
  4  5  2  0
 17 18  2  0
  1  3  2  0
 18 19  1  0
  5  6  1  0
 18 20  1  0
  8 11  1  0
 10 21  1  0
 21  1  1  0
  9 14  1  0
  1 22  1  0
 13 10  2  0
 22 23  2  0
 10 11  1  0
 23 24  1  0
  6  9  2  0
 24 25  2  0
 11 12  2  0
 25 26  1  0
 13 14  1  0
 26 27  2  0
 27 22  1  0
 25 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2023282

   [3-(3-Methylbut-2-enyl)-1,4-dioxonaphthalen-2-yl] 4-methylbenzenesulfonate

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: 396.46

Molecular Weight (Monoisotopic): 396.1031

AlogP: 4.39

#Rotatable Bonds: 5

Polar Surface Area: 77.51

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.62

CX LogD: 4.62

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.55

Np Likeness Score: 0.50

References

1. da Silva Júnior EN, de Melo IM, Diogo EB, Costa VA, de Souza Filho JD, Valença WO, Camara CA, de Oliveira RN, de Araujo AS, Emery FS, dos Santos MR, de Simone CA, Menna-Barreto RF, de Castro SL..  (2012)  On the search for potential anti-Trypanosoma cruzi drugs: synthesis and biological evaluation of 2-hydroxy-3-methylamino and 1,2,3-triazolic naphthoquinoidal compounds obtained by click chemistry reactions.,  52  [PMID:22483633] [10.1016/j.ejmech.2012.03.039]

2. Calil FA, David JS, Chiappetta ERC, Fumagalli F, Mello RB, Leite FHA, Castilho MS, Emery FS, Nonato MC..  (2019)  Ligand-based design, synthesis and biochemical evaluation of potent and selective inhibitors of Schistosoma mansoni dihydroorotate dehydrogenase.,  167  [PMID:30776695] [10.1016/j.ejmech.2019.02.018]

Source

Source(1):

• Scientific Literature