(S)-5-chloro-6-(4-(1-(4-chlorobenzyl)piperidin-4-yl)-3-ethylpiperazin-1-yl)-N-ethylnicotinamide

ID: ALA472288

Chembl Id: CHEMBL472288

Cas Number: 906556-51-2

PubChem CID: 44592137

Max Phase: Preclinical

Molecular Formula: C26H35Cl2N5O

Molecular Weight: 504.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNC(=O)c1cnc(N2CCN(C3CCN(Cc4ccc(Cl)cc4)CC3)[C@@H](CC)C2)c(Cl)c1

Standard InChI:  InChI=1S/C26H35Cl2N5O/c1-3-22-18-32(25-24(28)15-20(16-30-25)26(34)29-4-2)13-14-33(22)23-9-11-31(12-10-23)17-19-5-7-21(27)8-6-19/h5-8,15-16,22-23H,3-4,9-14,17-18H2,1-2H3,(H,29,34)/t22-/m0/s1

Standard InChI Key:  XQWKNLJIWOTOKT-QFIPXVFZSA-N

Alternative Forms

1. Parent:

   

   ALA472288

   (S)-5-chloro-6-(4-(1-(4-chlorobenzyl)piperidin-4-yl)-3-ethylpiperazin-1-yl)-N-ethylnicotinamide

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: 504.51

Molecular Weight (Monoisotopic): 503.2219

AlogP: 4.70

#Rotatable Bonds: 7

Polar Surface Area: 51.71

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.12

CX LogP: 4.63

CX LogD: 3.83

Aromatic Rings: 2

Heavy Atoms: 34

QED Weighted: 0.59

Np Likeness Score: -1.71

References

1. Wijtmans M, Verzijl D, van Dam CM, Bosch L, Smit MJ, Leurs R, de Esch IJ..  (2009)  Exploring a pocket for polycycloaliphatic groups in the CXCR3 receptor with the aid of a modular synthetic strategy.,  19  (8): [PMID:19299127] [10.1016/j.bmcl.2009.02.093]

2. Shao Y, Anilkumar GN, Carroll CD, Dong G, Hall JW, Hobbs DW, Jiang Y, Jenh CH, Kim SH, Kozlowski JA, McGuinness BF, Rosenblum SB, Schulman I, Shih NY, Shu Y, Wong MK, Yu W, Zawacki LG, Zeng Q..  (2011)  II. SAR studies of pyridyl-piperazinyl-piperidine derivatives as CXCR3 chemokine antagonists.,  21  (5): [PMID:21277198] [10.1016/j.bmcl.2010.12.114]

3. Kim SH, Anilkumar GN, Zawacki LG, Zeng Q, Yang DY, Shao Y, Dong G, Xu X, Yu W, Jiang Y, Jenh CH, Hall JW, Carroll CD, Hobbs DW, Baldwin JJ, McGuinness BF, Rosenblum SB, Kozlowski JA, Shankar BB, Shih NY..  (2011)  III. Identification of novel CXCR3 chemokine receptor antagonists with a pyrazinyl-piperazinyl-piperidine scaffold.,  21  (23): [PMID:22018463] [10.1016/j.bmcl.2011.09.120]

4. Arimont M, Sun SL, Leurs R, Smit M, de Esch IJP, de Graaf C..  (2017)  Structural Analysis of Chemokine Receptor-Ligand Interactions.,  60  (12): [PMID:28165741] [10.1021/acs.jmedchem.6b01309]

Source

Source(1):

• Scientific Literature