4-(4-Chloro-phenyl)-1,2,3,6-tetrahydro-pyridine

ID: ALA101664

Cas Number: 30005-58-4

PubChem CID: 185717

Max Phase: Preclinical

Molecular Formula: C11H12ClN

Molecular Weight: 193.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Clc1ccc(C2=CCNCC2)cc1

Standard InChI:  InChI=1S/C11H12ClN/c12-11-3-1-9(2-4-11)10-5-7-13-8-6-10/h1-5,13H,6-8H2

Standard InChI Key:  SXOMHACGFSJBIO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 13 14  0  0  0  0  0  0  0  0999 V2000
    5.1945   -3.0045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1969   -1.5045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8991   -0.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5965   -3.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8943   -3.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2328   -3.6062    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  7  8  1  0
  1  2  2  0
  3  4  2  0
  4  5  1  0
  2  3  1  0
  5  6  2  0
  7 12  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  4  7  1  0
  6  1  1  0
  1 13  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA101664

   4-(4-Chlorophenyl)-1,2,3,6-tetrahydropyridine

2. Alternative Forms:

   

   ALA101664

   4-(4-Chlorophenyl)-1，2，3，6-tetrahydropyridine hydrochloride

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: 193.68

Molecular Weight (Monoisotopic): 193.0658

AlogP: 2.72

#Rotatable Bonds: 1

Polar Surface Area: 12.03

Molecular Species: BASE

HBA: 1

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 1

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 9.58

CX LogP: 2.57

CX LogD: 0.42

Aromatic Rings: 1

Heavy Atoms: 13

QED Weighted: 0.72

Np Likeness Score: -0.14

References

1. Good AC, Peterson SJ, Richards WG..  (1993)  QSAR's from similarity matrices. Technique validation and application in the comparison of different similarity evaluation methods.,  36  (20): [PMID:8411009] [10.1021/jm00072a012]

2. Gessner W, Brossi A, Shen R, Abell CW..  (1985)  Synthesis and dihydropteridine reductase inhibitory effects of potential metabolites of the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine.,  28  (3): [PMID:3871859] [10.1021/jm00381a009]

3. Mabic S, Castagnoli N..  (1996)  Assessment of structural requirements for the monoamine oxidase-B-catalyzed oxidation of 1,4-disubstituted-1,2,3,6-tetrahydropyridine derivatives related to the neurotoxin 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine.,  39  (19): [PMID:8809158] [10.1021/jm9603882]

4. Schuster DI, Pan YP, Singh G, Stoupakis G, Cai B, Lem G, Ehrlich GK, Frietze W, Murphy RB..  (1993)  N-(1-arylpropionyl)-4-aryltetrahydropyridines, a new class of high-affinity selective sigma receptor ligands.,  36  (24): [PMID:7902869] [10.1021/jm00076a021]

5. Drug metabolism data, 

Source

Source(2):

• Scientific Literature
• Curated Drug Metabolism Pathways