(S)-5-chloro-6-(4-(1-(4-chloro-2-fluorobenzyl)piperidin-4-yl)-3-ethylpiperazin-1-yl)-N-ethylnicotinamide

ID: ALA1681882

Chembl Id: CHEMBL1681882

PubChem CID: 11569938

Max Phase: Preclinical

Molecular Formula: C26H34Cl2FN5O

Molecular Weight: 522.50

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNC(=O)c1cnc(N2CCN(C3CCN(Cc4ccc(Cl)cc4F)CC3)[C@@H](CC)C2)c(Cl)c1

Standard InChI:  InChI=1S/C26H34Cl2FN5O/c1-3-21-17-33(25-23(28)13-19(15-31-25)26(35)30-4-2)11-12-34(21)22-7-9-32(10-8-22)16-18-5-6-20(27)14-24(18)29/h5-6,13-15,21-22H,3-4,7-12,16-17H2,1-2H3,(H,30,35)/t21-/m0/s1

Standard InChI Key:  LXEUJQNDOXTGHH-NRFANRHFSA-N

Alternative Forms

1. Parent:

   

   ALA1681882

   (S)-5-chloro-6-(4-(1-(4-chloro-2-fluorobenzyl)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: 522.50

Molecular Weight (Monoisotopic): 521.2124

AlogP: 4.84

#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: 7.87

CX LogP: 4.78

CX LogD: 4.18

Aromatic Rings: 2

Heavy Atoms: 35

QED Weighted: 0.56

Np Likeness Score: -1.96

References

1. 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]

2. Nair AG, Wong MK, Shu Y, Jiang Y, Jenh CH, Kim SH, Yang DY, Zeng Q, Shao Y, Zawacki LG, Duo J, McGuinness BF, Carroll CD, Hobbs DW, Shih NY, Rosenblum SB, Kozlowski JA..  (2014)  IV. Discovery of CXCR3 antagonists substituted with heterocycles as amide surrogates: improved PK, hERG and metabolic profiles.,  24  (4): [PMID:24486132] [10.1016/j.bmcl.2014.01.009]

3. Mark Wenlock and Nicholas Tomkinson. Experimental in vitro DMPK and physicochemical data on a set of publicly disclosed compounds,  [10.6019/CHEMBL3301361]

4. Andrews SP, Cox RJ..  (2016)  Small Molecule CXCR3 Antagonists.,  59  (7): [PMID:26535614] [10.1021/acs.jmedchem.5b01337]

Source

Source(2):

• Scientific Literature
• AstraZeneca Deposited Data