6,7-dihydro-2-(4-ethylphenyl)-1,4-dithiepin-1,1,4,4-tetraoxide

ID: ALA3943955

PubChem CID: 9861140

Max Phase: Preclinical

Molecular Formula: C13H16O4S2

Molecular Weight: 300.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCc1ccc(C2=CS(=O)(=O)CCCS2(=O)=O)cc1

Standard InChI:  InChI=1S/C13H16O4S2/c1-2-11-4-6-12(7-5-11)13-10-18(14,15)8-3-9-19(13,16)17/h4-7,10H,2-3,8-9H2,1H3

Standard InChI Key:  UJIWLLJEAGNPFO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
   17.2350   -7.6929    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6515   -8.4093    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.0637   -7.6903    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2205  -11.0355    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2246  -10.2105    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.5052  -10.6195    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9115   -8.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3958   -8.7811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5718   -9.5851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7168   -9.5650    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0526  -10.2202    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2730   -8.2392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4085   -7.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7708   -6.9038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9985   -7.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8678   -8.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5067   -8.5324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3533   -6.6697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5750   -6.9656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
 10  5  1  0
  7 10  2  0
  5  4  2  0
  2  8  1  0
  6  5  2  0
  5 11  1  0
  8  9  1  0
  9 11  1  0
  7  2  1  0
  7 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 15 18  1  0
 18 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3943955

   2-(4-ethylphenyl)-6,7-dihydro-5H-1,4-dithiepine 1,1,4,4-tetraoxide

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: 300.40

Molecular Weight (Monoisotopic): 300.0490

AlogP: 1.78

#Rotatable Bonds: 2

Polar Surface Area: 68.28

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 0.58

CX LogD: 0.58

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.83

Np Likeness Score: -0.50

References

1.  (2002)  1,4-dithiin and 1,4-dithiepin-1,1,4,4, tetroxide derivatives useful as antagonists of the human galanin receptor, 

2. Scott, M K MK and 9 more authors.  2000-06  2,3-Dihydro-dithiin and -dithiepine-1,1,4,4-tetroxides: small molecule non-peptide antagonists of the human galanin hGAL-1 receptor.  [PMID:10896115]

3. Bulaj, Grzegorz G and 11 more authors.  2008-12-25  Design, synthesis, and characterization of high-affinity, systemically-active galanin analogues with potent anticonvulsant activities.  [PMID:19053761]

4. Zhang, Liuyin L and 5 more authors.  2009-03-12  Structural requirements for a lipoamino acid in modulating the anticonvulsant activities of systemically active galanin analogues.  [PMID:19199479]

5. Robertson, Charles R and 5 more authors.  2010-02-25  Engineering galanin analogues that discriminate between GalR1 and GalR2 receptor subtypes and exhibit anticonvulsant activity following systemic delivery.  [PMID:20121116]

6. Green, Brad R BR and 5 more authors.  2013-01-01  Cyclic analogs of galanin and neuropeptide Y by hydrocarbon stapling.  [PMID:23176753]

Source

Source(1):

• Patent Bioactivity Data