(S)-2-[1-(Biphenyl-4-ylmethyl)-4-(cyclohexylmethyl)piperazin-2-yl]ethanol

ID: ALA3104856

Chembl Id: CHEMBL3104856

PubChem CID: 73056461

Max Phase: Preclinical

Molecular Formula: C26H36N2O

Molecular Weight: 392.59

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OCC[C@H]1CN(CC2CCCCC2)CCN1Cc1ccc(-c2ccccc2)cc1

Standard InChI:  InChI=1S/C26H36N2O/c29-18-15-26-21-27(19-22-7-3-1-4-8-22)16-17-28(26)20-23-11-13-25(14-12-23)24-9-5-2-6-10-24/h2,5-6,9-14,22,26,29H,1,3-4,7-8,15-21H2/t26-/m0/s1

Standard InChI Key:  HYJVYRBGCPGOSX-SANMLTNESA-N

Alternative Forms

1. Parent:

   

   ALA3104856

   2-[(2S)-4-(cyclohexylmethyl)-1-[(4-phenylphenyl)methyl]piperazin-2-yl]ethanol

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: 392.59

Molecular Weight (Monoisotopic): 392.2828

AlogP: 4.80

#Rotatable Bonds: 7

Polar Surface Area: 26.71

Molecular Species: BASE

HBA: 3

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa: 8.97

CX LogP: 4.95

CX LogD: 3.38

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.73

Np Likeness Score: -0.83

References

1. Korpis K, Weber F, Brune S, Wünsch B, Bednarski PJ..  (2014)  Involvement of apoptosis and autophagy in the death of RPMI 8226 multiple myeloma cells by two enantiomeric sigma receptor ligands.,  22  (1): [PMID:24331758] [10.1016/j.bmc.2013.11.033]

2. Weber F, Brune S, Korpis K, Bednarski PJ, Laurini E, Dal Col V, Pricl S, Schepmann D, Wünsch B..  (2014)  Synthesis, pharmacological evaluation, and σ1 receptor interaction analysis of hydroxyethyl substituted piperazines.,  57  (7): [PMID:24617836] [10.1021/jm401707t]

3. Fallica AN, Ciaffaglione V, Modica MN, Pittalà V, Salerno L, Amata E, Marrazzo A, Romeo G, Intagliata S..  (2022)  Structure-activity relationships of mixed σ₁R/σ₂R ligands with antiproliferative and anticancer effects.,  73  [PMID:36202063] [10.1016/j.bmc.2022.117032]

Source

Source(1):

• Scientific Literature