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

ID: ALA3342864

PubChem CID: 118716711

Max Phase: Preclinical

Molecular Formula: C21H31N3O4

Molecular Weight: 389.50

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C21H31N3O4/c1-17(25)23-9-7-21(8-10-23)27-16-18(28-21)15-22-11-13-24(14-12-22)19-5-3-4-6-20(19)26-2/h3-6,18H,7-16H2,1-2H3

Standard InChI Key:  ZPEUIKDDMPOHBF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 31  0  0  0  0  0  0  0  0999 V2000
    5.7330  -19.5510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9229  -20.3486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7404  -20.4132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0574  -19.6595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4331  -19.1252    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3379  -18.6931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3167  -19.5141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0154  -19.9409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7563  -18.7297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0578  -18.2988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1710  -21.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9921  -21.0936    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4143  -21.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2319  -21.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6303  -21.0556    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2009  -20.3525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3771  -20.3698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4483  -21.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8716  -21.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6920  -21.7238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0900  -21.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6576  -20.2976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8387  -20.3184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4129  -19.6168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8041  -18.8993    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6403  -18.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6601  -17.4505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9229  -18.6588    0.0000 C   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
M  END

Alternative Forms

1. Parent:

   

   ALA3342864

   ---

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: 389.50

Molecular Weight (Monoisotopic): 389.2315

AlogP: 1.57

#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: 1.74

CX LogD: 1.48

Aromatic Rings: 1

Heavy Atoms: 28

QED Weighted: 0.78

Np Likeness Score: -0.93

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