(1S)-1-(2-((S)-4-(6-fluoronaphthalen-1-yl)-2-methylpiperazin-1-yl)ethyl)-1,3,7,7a-tetrahydroisobenzofuran-5-carboxamide

ID: ALA3706923

PubChem CID: 122197403

Max Phase: Preclinical

Molecular Formula: C26H28FN3O2

Molecular Weight: 433.53

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C[C@H]1CN(c2cccc3cc(F)ccc23)CCN1CC[C@@H]1OCc2cc(C(N)=O)ccc21

Standard InChI:  InChI=1S/C26H28FN3O2/c1-17-15-30(24-4-2-3-18-14-21(27)6-8-22(18)24)12-11-29(17)10-9-25-23-7-5-19(26(28)31)13-20(23)16-32-25/h2-8,13-14,17,25H,9-12,15-16H2,1H3,(H2,28,31)/t17-,25-/m0/s1

Standard InChI Key:  IEEIKXULGHBDHP-GKVSMKOHSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  1  0  0  0  0  0999 V2000
   11.3739   -2.4066    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3727   -3.2340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0875   -3.6468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0857   -1.9938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6593   -1.9943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6591   -1.1693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9449   -2.4069    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.8016   -2.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8045   -3.2358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5984   -3.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0862   -2.8144    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5937   -2.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6007   -4.3157    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3162   -4.7263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0296   -4.3118    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7477   -4.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4590   -4.3105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4610   -3.4851    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.7455   -3.0724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0281   -3.4850    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1759   -3.0734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8868   -3.4891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6012   -3.0780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6026   -2.2521    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1720   -2.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8820   -1.8431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8814   -1.0254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1717   -0.6161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4610   -1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4650   -1.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1697    0.2089    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.7500   -5.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
  5  7  1  0
  8  9  1  0
  1  2  2  0
  8  4  2  0
  4  1  1  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 18 21  1  0
  1  5  1  0
 21 22  2  0
  9 10  1  0
 22 23  1  0
 10 11  1  0
 23 24  2  0
 24 26  1  0
 25 21  1  0
 11 12  1  0
 12  8  1  0
 25 26  1  0
  2  3  1  0
 26 27  2  0
 10 13  1  1
 27 28  1  0
  5  6  2  0
 28 29  2  0
 13 14  1  0
 29 30  1  0
 30 25  2  0
  9  3  2  0
 28 31  1  0
 14 15  1  0
 16 32  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA3706923

   ---

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: 433.53

Molecular Weight (Monoisotopic): 433.2166

AlogP: 4.25

#Rotatable Bonds: 5

Polar Surface Area: 58.80

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 8.65

CX LogP: 3.88

CX LogD: 2.60

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.65

Np Likeness Score: -0.91

References

1. Bueno AB, Gilmore J, Boot J, Broadmore R, Cooper J, Findlay J, Hayhurst L, Marcos A, Montero C, Mitchell S, Timms G, Tomlinson R, Wallace L, Walton L..  (2007)  Naphthyl piperazines with dual activity as 5-HT1D antagonists and 5-HT reuptake inhibitors.,  17  (12): [PMID:17434731] [10.1016/j.bmcl.2007.03.101]

Source

Source(1):

• Scientific Literature