(3S,4R)-3-((6-aminohexyl)amino)-4-((3,4-dichlorophenyl)sulfonyl)tetrahydrothiophene 1,1-dioxide

ID: ALA5281401

Max Phase: Preclinical

Molecular Formula: C16H24Cl2N2O4S2

Molecular Weight: 443.42

Names and Identifiers

Canonical SMILES:  NCCCCCCN[C@H]1CS(=O)(=O)C[C@@H]1S(=O)(=O)c1ccc(Cl)c(Cl)c1

Standard InChI:  InChI=1S/C16H24Cl2N2O4S2/c17-13-6-5-12(9-14(13)18)26(23,24)16-11-25(21,22)10-15(16)20-8-4-2-1-3-7-19/h5-6,9,15-16,20H,1-4,7-8,10-11,19H2/t15-,16-/m0/s1

Standard InChI Key:  IIOZKTHYLGXAIC-HOTGVXAUSA-N

Molfile:  

 
     RDKit          2D

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    0.2071    0.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0321    0.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2823   -0.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6287   -1.0498    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0387   -0.5578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2052    0.9391    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0300    0.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4423    0.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2672    0.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4444    0.9391    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.2693    0.9391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6820    1.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5043    1.6526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9168    0.9381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5078    0.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6835    0.2218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7416    0.9381    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.9202   -0.4877    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.4444    1.7655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7307    1.3524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2156   -1.7655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0403   -1.7655    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6796   -0.4893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5045   -0.4893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9168   -1.2037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7416   -1.2037    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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  3  4  1  0
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  1  6  1  6
  6  7  1  0
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  2 10  1  1
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 10 19  2  0
 10 20  2  0
  4 21  2  0
  4 22  2  0
  9 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA5281401

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 443.42

Molecular Weight (Monoisotopic): 442.0555

AlogP: 2.04

#Rotatable Bonds: 9

Polar Surface Area: 106.33

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 10.21

CX LogP: 1.41

CX LogD: -1.40

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.57

Np Likeness Score: -1.15

References

1. Jo J, Kim J, Ibrahim L, Kumar M, Iaconelli J, Tran CS, Moon HR, Jung Y, Wiseman RL, Lairson LL, Chatterjee AK, Bollong MJ, Yun H..  (2023)  Optimization of 3-aminotetrahydrothiophene 1,1-dioxides with improved potency and efficacy as non-electrophilic antioxidant response element (ARE) activators.,  89  [PMID:37116763] [10.1016/j.bmcl.2023.129306]

Source

Source(1):

• Scientific Literature