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

ID: ALA3342861

PubChem CID: 118716708

Max Phase: Preclinical

Molecular Formula: C24H31N3O5

Molecular Weight: 441.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1N1CCN(CC2COC3(CCN(C(=O)c4ccco4)CC3)O2)CC1

Standard InChI:  InChI=1S/C24H31N3O5/c1-29-21-6-3-2-5-20(21)26-14-12-25(13-15-26)17-19-18-31-24(32-19)8-10-27(11-9-24)23(28)22-7-4-16-30-22/h2-7,16,19H,8-15,17-18H2,1H3

Standard InChI Key:  RMARPDOMKGOSCL-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    4.2348  -25.2796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4247  -26.0772    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2422  -26.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5592  -25.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9349  -24.8538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8397  -24.4217    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8185  -25.2427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5172  -25.6695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2581  -24.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5596  -24.0274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6728  -26.8430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4939  -26.8222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9162  -27.5232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7337  -27.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1321  -26.7842    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7027  -26.0811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8790  -26.0984    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9501  -26.7653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3734  -27.4697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1938  -27.4524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5919  -26.7313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1595  -26.0262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3405  -26.0470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9147  -25.3454    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3059  -24.6279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1421  -23.9961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1619  -23.1791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4247  -24.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6815  -24.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1201  -24.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5115  -25.3506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3147  -25.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  1  0
  6  7  1  0
  6 10  1  0
  7  8  1  0
  8  1  1  0
  1  9  1  0
  9 10  1  0
  3 11  1  0
 11 12  1  0
 12 13  1  0
 12 17  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
 15 18  1  0
 23 24  1  0
 24 25  1  0
  6 26  1  0
 26 27  2  0
 26 28  1  0
 28 29  2  0
 29 30  1  0
 30 31  2  0
 31 32  1  0
 32 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3342861

   ---

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: 441.53

Molecular Weight (Monoisotopic): 441.2264

AlogP: 2.46

#Rotatable Bonds: 5

Polar Surface Area: 67.62

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: 2.65

CX LogD: 2.39

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.71

Np Likeness Score: -1.17

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