4-[(7-chloroquinolin-4-yl)amino]-2-(diethylaminomethyl)phenol dihydrochloride

ID: ALA3216010

Chembl Id: CHEMBL3216010

PubChem CID: 90664548

Max Phase: Preclinical

Molecular Formula: C20H25Cl4N3O

Molecular Weight: 355.87

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)Cc1cc(Nc2ccnc3cc(Cl)ccc23)ccc1O.Cl.Cl.Cl

Standard InChI:  InChI=1S/C20H22ClN3O.3ClH/c1-3-24(4-2)13-14-11-16(6-8-20(14)25)23-18-9-10-22-19-12-15(21)5-7-17(18)19;;;/h5-12,25H,3-4,13H2,1-2H3,(H,22,23);3*1H

Standard InChI Key:  XASZDHUZFUQQKH-UHFFFAOYSA-N

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: 355.87

Molecular Weight (Monoisotopic): 355.1451

AlogP: 5.18

#Rotatable Bonds: 6

Polar Surface Area: 48.39

Molecular Species: BASE

HBA: 4

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.10

CX Basic pKa: 10.17

CX LogP: 3.80

CX LogD: 2.32

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.60

Np Likeness Score: -1.16

References

1. Zsila F, Visy J, Mády G, Fitos I..  (2008)  Selective plasma protein binding of antimalarial drugs to alpha1-acid glycoprotein.,  16  (7): [PMID:18289858] [10.1016/j.bmc.2008.01.053]

2. O'Neill PM, Shone AE, Stanford D, Nixon G, Asadollahy E, Park BK, Maggs JL, Roberts P, Stocks PA, Biagini G, Bray PG, Davies J, Berry N, Hall C, Rimmer K, Winstanley PA, Hindley S, Bambal RB, Davis CB, Bates M, Gresham SL, Brigandi RA, Gomez-de-Las-Heras FM, Gargallo DV, Parapini S, Vivas L, Lander H, Taramelli D, Ward SA..  (2009)  Synthesis, antimalarial activity, and preclinical pharmacology of a novel series of 4'-fluoro and 4'-chloro analogues of amodiaquine. Identification of a suitable "back-up" compound for N-tert-butyl isoquine.,  52  (7): [PMID:19284751] [10.1021/jm8012757]

3. Gamo FJ, Sanz LM, Vidal J, de Cozar C, Alvarez E, Lavandera JL, Vanderwall DE, Green DV, Kumar V, Hasan S, Brown JR, Peishoff CE, Cardon LR, Garcia-Bustos JF..  (2010)  Thousands of chemical starting points for antimalarial lead identification.,  465  (7296): [PMID:20485427] [10.1038/nature09107]

4. Greene N, Fisk L, Naven RT, Note RR, Patel ML, Pelletier DJ..  (2010)  Developing structure-activity relationships for the prediction of hepatotoxicity.,  23  (7): [PMID:20553011] [10.1021/tx1000865]

5. Ekins S, Williams AJ, Xu JJ..  (2010)  A predictive ligand-based Bayesian model for human drug-induced liver injury.,  38  (12): [PMID:20843939] [10.1124/dmd.110.035113]

6. Liu Z, Shi Q, Ding D, Kelly R, Fang H, Tong W..  (2011)  Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).,  7  (12): [PMID:22194678] [10.1371/journal.pcbi.1002310]

7. Tukulula M, Njoroge M, Mugumbate GC, Gut J, Rosenthal PJ, Barteau S, Streckfuss J, Heudi O, Kameni-Tcheudji J, Chibale K..  (2013)  Tetrazole-based deoxyamodiaquines: synthesis, ADME/PK profiling and pharmacological evaluation as potential antimalarial agents.,  21  (17): [PMID:23896611] [10.1016/j.bmc.2013.06.067]

8. St. Jude Leishmania screening dataset.,  [10.6019/CHEMBL3433997]

Source

Source(3):

• Scientific Literature
• GSK Malaria Screening
• St Jude Leishmania Screening