2,2,2-Trifluoro-1-(2-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-1,4-dioxa-8-azaspiro[4.5]decan-8-yl)ethan-1-one

ID: ALA3342865

PubChem CID: 118716712

Max Phase: Preclinical

Molecular Formula: C21H28F3N3O4

Molecular Weight: 443.47

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H28F3N3O4/c1-29-18-5-3-2-4-17(18)26-12-10-25(11-13-26)14-16-15-30-20(31-16)6-8-27(9-7-20)19(28)21(22,23)24/h2-5,16H,6-15H2,1H3

Standard InChI Key:  RPHOENXERNUVOJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    4.3050  -15.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4949  -16.2049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3124  -16.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6293  -15.5158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0051  -14.9814    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9099  -14.5494    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.8887  -15.3704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5873  -15.7972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3282  -14.5860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6298  -14.1551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7430  -16.9707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5641  -16.9499    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9863  -17.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8039  -17.6321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2023  -16.9118    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7729  -16.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9491  -16.2260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0203  -16.8929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4436  -17.5974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2639  -17.5800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6620  -16.8590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2296  -16.1539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4107  -16.1747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9849  -15.4731    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3761  -14.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2123  -14.1238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2321  -13.3068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4949  -14.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7973  -14.0895    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4751  -15.3320    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.7842  -14.9158    0.0000 F   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  1  0
 28 30  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3342865

   ---

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: 443.47

Molecular Weight (Monoisotopic): 443.2032

AlogP: 2.11

#Rotatable Bonds: 4

Polar Surface Area: 54.48

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.32

CX LogP: 2.87

CX LogD: 2.61

Aromatic Rings: 1

Heavy Atoms: 31

QED Weighted: 0.71

Np Likeness Score: -1.09

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