Isopropyl-(1S,2S)-2-((4-(4-chlorophenyl)-4-hydroxypiperidin-1-yl)methyl)-1-phenylcyclopropane-1-carboxylate

ID: ALA4076839

PubChem CID: 137651188

Max Phase: Preclinical

Molecular Formula: C25H30ClNO3

Molecular Weight: 427.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)OC(=O)[C@@]1(c2ccccc2)C[C@@H]1CN1CCC(O)(c2ccc(Cl)cc2)CC1

Standard InChI:  InChI=1S/C25H30ClNO3/c1-18(2)30-23(28)25(20-6-4-3-5-7-20)16-21(25)17-27-14-12-24(29,13-15-27)19-8-10-22(26)11-9-19/h3-11,18,21,29H,12-17H2,1-2H3/t21-,25-/m1/s1

Standard InChI Key:  FGUAQYXGDVSXPL-PXDATVDWSA-N

Molfile:  

     RDKit          2D

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   13.2511   -8.5728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4771   -8.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6190   -8.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8831   -8.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6571   -8.3262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7411   -7.2352    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6633   -9.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4876   -9.2880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8998  -10.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4876  -10.7186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6633  -10.7186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2511  -10.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9449   -9.4904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1354   -9.3443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6073   -9.9763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7937   -9.8344    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5121   -9.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0402   -8.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8539   -8.5704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9842   -8.4283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7968   -9.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7968  -10.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0816  -10.7091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3705  -10.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3705   -9.4726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0816   -9.0604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6552  -10.7091    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   14.3691   -6.7030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2271   -5.8935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1472   -6.9844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  1  3  1  0
  4  5  2  0
  4  6  1  0
  1  4  1  6
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
  7 12  2  0
  1  7  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 14 19  1  0
 17 20  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
 24 27  1  0
 17 21  1  0
 13 14  1  0
  2 13  1  1
 28 29  1  0
 28 30  1  0
  6 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4076839

   ---

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: 427.97

Molecular Weight (Monoisotopic): 427.1914

AlogP: 4.53

#Rotatable Bonds: 6

Polar Surface Area: 49.77

Molecular Species: BASE

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.96

CX Basic pKa: 8.61

CX LogP: 4.37

CX LogD: 3.14

Aromatic Rings: 2

Heavy Atoms: 30

QED Weighted: 0.69

Np Likeness Score: -0.15

References

1. Amata E, Rescifina A, Prezzavento O, Arena E, Dichiara M, Pittalà V, Montilla-García Á, Punzo F, Merino P, Cobos EJ, Marrazzo A..  (2018)  (+)-Methyl (1R,2S)-2-{[4-(4-Chlorophenyl)-4-hydroxypiperidin-1-yl]methyl}-1-phenylcyclopropanecarboxylate [(+)-MR200] Derivatives as Potent and Selective Sigma Receptor Ligands: Stereochemistry and Pharmacological Properties.,  61  (1): [PMID:29220177] [10.1021/acs.jmedchem.7b01584]

Source

Source(1):

• Scientific Literature