8-Methanesulfonyl-2-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-1,4-dioxa-8-azaspiro[4.5]decane

ID: ALA3342873

PubChem CID: 118716720

Max Phase: Preclinical

Molecular Formula: C20H31N3O5S

Molecular Weight: 425.55

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1N1CCN(CC2COC3(CCN(S(C)(=O)=O)CC3)O2)CC1

Standard InChI:  InChI=1S/C20H31N3O5S/c1-26-19-6-4-3-5-18(19)22-13-11-21(12-14-22)15-17-16-27-20(28-17)7-9-23(10-8-20)29(2,24)25/h3-6,17H,7-16H2,1-2H3

Standard InChI Key:  BWIJSERURKMDCF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    3.5577  -20.5412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9704  -21.2511    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.3788  -20.5387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0632  -22.5349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2531  -23.3326    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0706  -23.3972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3875  -22.6435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7633  -22.1092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6681  -21.6771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6469  -22.4981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3455  -22.9249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0864  -21.7137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3880  -21.2828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5012  -24.0984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3223  -24.0776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7445  -24.7786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5621  -24.7598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9605  -24.0395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5311  -23.3365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7073  -23.3538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7785  -24.0207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2018  -24.7251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0221  -24.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4202  -23.9867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9878  -23.2816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1689  -23.3024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7431  -22.6008    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.1343  -21.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2531  -21.6428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  4  1  0
  9 10  1  0
  9 13  1  0
 10 11  1  0
 11  4  1  0
  4 12  1  0
 12 13  1  0
  6 14  1  0
 14 15  1  0
 15 16  1  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 18 21  1  0
 26 27  1  0
 27 28  1  0
  9  2  1  0
  2 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3342873

   ---

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: 425.55

Molecular Weight (Monoisotopic): 425.1984

AlogP: 0.98

#Rotatable Bonds: 5

Polar Surface Area: 71.55

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.32

CX LogP: 1.23

CX LogD: 0.97

Aromatic Rings: 1

Heavy Atoms: 29

QED Weighted: 0.70

Np Likeness Score: -1.14

References

1. Franchini S, Battisti UM, Baraldi A, Prandi A, Fossa P, Cichero E, Tait A, Sorbi C, Marucci G, Cilia A, Pirona L, Brasili L..  (2014)  Structure-affinity/activity relationships of 1,4-dioxa-spiro[4.5]decane based ligands at α1 and 5-HT1A receptors.,  87  [PMID:25261823] [10.1016/j.ejmech.2014.09.070]

Source

Source(1):

• Scientific Literature