| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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ID: ALA472288
Max Phase: Preclinical
Molecular Formula: C26H35Cl2N5O
Molecular Weight: 504.51
Molecule Type: Small molecule
Associated Items:
Representations
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
Associated Targets(Human)
C-X-C chemokine receptor type 3 2736 Activities
Associated Targets(non-human)
Rattus norvegicus 775804 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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C-X-C chemokine receptor type 3 96 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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C-X-C chemokine receptor type 3 21 Activities
| Activity Type | Relation | Activity value | Units | Action Type | Journal | PubMed Id | doi | Assay Aladdin ID |
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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 |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
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Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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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):