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

ID: ALA3980007

PubChem CID: 91480105

Max Phase: Preclinical

Molecular Formula: C17H22O4S2

Molecular Weight: 354.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=S1(=O)C=C(c2ccc(C3CCCCC3)cc2)S(=O)(=O)CCC1

Standard InChI:  InChI=1S/C17H22O4S2/c18-22(19)11-4-12-23(20,21)17(13-22)16-9-7-15(8-10-16)14-5-2-1-3-6-14/h7-10,13-14H,1-6,11-12H2

Standard InChI Key:  MWEWMWQBVCJDMA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
   21.1202   -9.6034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4436  -11.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4415  -11.0501    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.7277  -11.4664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.3755   -8.5081    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8550   -9.2482    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   22.2744   -8.4714    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6006   -9.6090    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9283  -10.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.7881  -10.4116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2692  -11.0535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4775   -9.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6041   -8.2710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9613   -7.7537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1920   -8.0517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0654   -8.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7082   -9.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5493   -7.5344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6759   -6.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0331   -6.2020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2638   -6.4999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1373   -7.3152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7800   -7.8324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0
  4  3  2  0
  6  5  2  0
  7  6  2  0
  1  6  1  0
  6  8  1  0
  1  9  2  0
  8 10  1  0
  9  3  1  0
 10 11  1  0
  3 11  1  0
  1 12  1  0
 12 13  2  0
 12 17  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 15 18  1  0
 18 19  1  0
 18 23  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3980007

   2-(4-cyclohexylphenyl)-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: 354.49

Molecular Weight (Monoisotopic): 354.0960

AlogP: 3.27

#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: 1.73

CX LogD: 1.73

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.82

Np Likeness Score: -0.26

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