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

ID: ALA3939021

PubChem CID: 101061658

Max Phase: Preclinical

Molecular Formula: C12H14O5S2

Molecular Weight: 302.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1C1=CS(=O)(=O)CCCS1(=O)=O

Standard InChI:  InChI=1S/C12H14O5S2/c1-17-11-6-3-2-5-10(11)12-9-18(13,14)7-4-8-19(12,15)16/h2-3,5-6,9H,4,7-8H2,1H3

Standard InChI Key:  IOKNUEXREUPODF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
   17.2430   -7.6964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6597   -8.4132    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.0720   -7.6939    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2284  -11.0406    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.2326  -10.2152    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.5128  -10.6243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9193   -8.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4043   -8.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5803   -9.5895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7245   -9.5694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0609  -10.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2805   -8.2430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4161   -7.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7781   -6.9070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0054   -7.1991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8747   -8.0180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5139   -8.5363    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3828   -9.3589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5783   -9.5744    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
 17 18  1  0
 18 19  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3939021

   2-(2-methoxyphenyl)-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: 302.37

Molecular Weight (Monoisotopic): 302.0283

AlogP: 1.23

#Rotatable Bonds: 2

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: -0.54

CX LogD: -0.54

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.82

Np Likeness Score: -0.35

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