N-(3-{4-[3-(7-Chloro-quinolin-4-ylamino)-propyl]-piperazin-1-yl}-propyl)-N'-hydroxy-N-isobutyl-malonamide

ID: ALA328470

Chembl Id: CHEMBL328470

PubChem CID: 9849506

Max Phase: Preclinical

Molecular Formula: C26H39ClN6O3

Molecular Weight: 519.09

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)CN(CCCN1CCN(CCCNc2ccnc3cc(Cl)ccc23)CC1)C(=O)CC(=O)NO

Standard InChI:  InChI=1S/C26H39ClN6O3/c1-20(2)19-33(26(35)18-25(34)30-36)12-4-11-32-15-13-31(14-16-32)10-3-8-28-23-7-9-29-24-17-21(27)5-6-22(23)24/h5-7,9,17,20,36H,3-4,8,10-16,18-19H2,1-2H3,(H,28,29)(H,30,34)

Standard InChI Key:  VVFDRGRIBSABAD-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA328470

   N'-[3-[4-[3-[(7-chloroquinolin-4-yl)amino]propyl]piperazin-1-yl]propyl]-N-hydroxy-N'-(2-methylpropyl)propanediamide

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: 519.09

Molecular Weight (Monoisotopic): 518.2772

AlogP: 3.08

#Rotatable Bonds: 13

Polar Surface Area: 101.04

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.91

CX Basic pKa: 8.11

CX LogP: 1.30

CX LogD: 0.73

Aromatic Rings: 2

Heavy Atoms: 36

QED Weighted: 0.16

Np Likeness Score: -1.32

References

1. Flipo M, Florent I, Grellier P, Sergheraert C, Deprez-Poulain R..  (2003)  Design, synthesis and antimalarial activity of novel, quinoline-based, zinc metallo-aminopeptidase inhibitors.,  13  (16): [PMID:12873488] [10.1016/s0960-894x(03)00550-x]

2. Amin SA, Adhikari N, Jha T..  (2018)  Design of Aminopeptidase N Inhibitors as Anti-cancer Agents.,  61  (15): [PMID:29630364] [10.1021/acs.jmedchem.7b00782]

3. Mills B, Isaac RE, Foster R..  (2021)  Metalloaminopeptidases of the Protozoan Parasite Plasmodium falciparum as Targets for the Discovery of Novel Antimalarial Drugs.,  64  (4.0): [PMID:33534577] [10.1021/acs.jmedchem.0c01721]

Source

Source(1):

• Scientific Literature