(-)-R-1-(1-(5-chlorothiophen-3-yl)-2-(4-methylpiperazin-1-yl)ethyl)cyclohexanol

ID: ALA1099178

PubChem CID: 11210071

Max Phase: Preclinical

Molecular Formula: C17H27ClN2OS

Molecular Weight: 342.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN1CCN(C[C@@H](c2csc(Cl)c2)C2(O)CCCCC2)CC1

Standard InChI:  InChI=1S/C17H27ClN2OS/c1-19-7-9-20(10-8-19)12-15(14-11-16(18)22-13-14)17(21)5-3-2-4-6-17/h11,13,15,21H,2-10,12H2,1H3/t15-/m0/s1

Standard InChI Key:  KHYNNQYNYMSTIB-HNNXBMFYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
   -1.0775   -1.6697    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4917   -0.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9332   -0.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1892   -0.6702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2743   -1.4883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3121   -0.8752    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.5254   -0.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6181    1.8045    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6174    0.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9030    0.5686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1888    0.9795    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1890    1.8054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9033    2.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5254    0.5672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2392   -0.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7075   -1.3008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9876   -2.0764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8000   -2.2201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3323   -1.5876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0522   -0.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5200    0.1050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3323    2.2168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
  7 14  1  6
  7 15  1  0
 15 16  1  0
  4  7  1  0
  8  9  1  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
 15 20  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
  4  5  2  0
 15 21  1  0
  5  1  1  0
  8 22  1  0
  2  6  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1099178

   (-)-R-1-(1-(5-chlorothiophen-3-yl)-2-(4-methylpiperazin-1-yl)ethyl)cyclohexanol

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: 342.94

Molecular Weight (Monoisotopic): 342.1533

AlogP: 3.43

#Rotatable Bonds: 4

Polar Surface Area: 26.71

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 7.75

CX LogP: 3.29

CX LogD: 2.78

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.91

Np Likeness Score: -0.49

References

1. Sabatucci JP, Mahaney PE, Leiter J, Johnston G, Burroughs K, Cosmi S, Zhang Y, Ho D, Deecher DC, Trybulski E..  (2010)  Heterocyclic cycloalkanol ethylamines as norepinephrine reuptake inhibitors.,  20  (9): [PMID:20378347] [10.1016/j.bmcl.2010.03.059]

Source

Source(1):

• Scientific Literature