2-{[4-(2-Methoxyphenyl)piperazin-1-yl]methyl}-8-(thiophene-2-sulfonyl)-1,4-dioxa-8-azaspiro[4.5]decane

ID: ALA3342872

PubChem CID: 118716719

Max Phase: Preclinical

Molecular Formula: C23H31N3O5S2

Molecular Weight: 493.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1N1CCN(CC2COC3(CCN(S(=O)(=O)c4cccs4)CC3)O2)CC1

Standard InChI:  InChI=1S/C23H31N3O5S2/c1-29-21-6-3-2-5-20(21)25-14-12-24(13-15-25)17-19-18-30-23(31-19)8-10-26(11-9-23)33(27,28)22-7-4-16-32-22/h2-7,16,19H,8-15,17-18H2,1H3

Standard InChI Key:  BHUCMEWUSAGOPR-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.8371  -15.6835    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2498  -16.3934    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.6583  -15.6810    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3426  -17.6772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5325  -18.4748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3500  -18.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6670  -17.7858    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0427  -17.2514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9476  -16.8193    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9263  -17.6404    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6250  -18.0672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659  -16.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6674  -16.4251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7806  -19.2406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6017  -19.2198    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.0240  -19.9209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   11.2399  -19.1818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   12.0579  -19.1629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4812  -19.8674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3016  -19.8500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6997  -19.1289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2673  -18.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4483  -18.4447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0226  -17.7430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4137  -17.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5325  -16.7851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7932  -16.4392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2320  -17.0334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6238  -17.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4269  -17.5997    0.0000 S   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
 29 30  2  0
 30 31  1  0
 31 32  2  0
 32 33  1  0
 33 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3342872

   ---

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: 493.65

Molecular Weight (Monoisotopic): 493.1705

AlogP: 2.48

#Rotatable Bonds: 6

Polar Surface Area: 71.55

Molecular Species: NEUTRAL

HBA: 8

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.32

CX LogP: 3.30

CX LogD: 3.03

Aromatic Rings: 2

Heavy Atoms: 33

QED Weighted: 0.61

Np Likeness Score: -1.55

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