rac-5-nitro-7-((3-phenylpyrrolidin-1-yl)methyl)quinolin-8-ol

ID: ALA2023324

Chembl Id: CHEMBL2023324

PubChem CID: 2921529

Max Phase: Preclinical

Molecular Formula: C20H19N3O3

Molecular Weight: 349.39

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  O=[N+]([O-])c1cc(CN2CCC(c3ccccc3)C2)c(O)c2ncccc12

Standard InChI:  InChI=1S/C20H19N3O3/c24-20-16(11-18(23(25)26)17-7-4-9-21-19(17)20)13-22-10-8-15(12-22)14-5-2-1-3-6-14/h1-7,9,11,15,24H,8,10,12-13H2

Standard InChI Key:  NCXLPGIFFKJJHL-UHFFFAOYSA-N

Alternative Forms

  1. Parent:

Associated Targets(Human)

HeLa (62764 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

yopH Tyrosine-protein phosphatase yopH (57 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chlamydia trachomatis (699 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Yersinia pseudotuberculosis (544 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
J774 (3120 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Chlamydia (5 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Small moleculeTopical: NoFirst In Class: NoBlack Box: No
Chirality: NoAvailability: NoProdrug: No

Drug Indications

MESH IDMESH Heading EFO IDsEFO TermsMax Phase for IndicationReferences

Mechanisms of Action

Mechanism of ActionAction Typetarget IDTarget NameTarget TypeTarget OrganismBinding Site NameReferences

Calculated Properties

Molecular Weight: 349.39Molecular Weight (Monoisotopic): 349.1426AlogP: 3.84#Rotatable Bonds: 4
Polar Surface Area: 79.50Molecular Species: ZWITTERIONHBA: 5HBD: 1
#RO5 Violations: HBA (Lipinski): 6HBD (Lipinski): 1#RO5 Violations (Lipinski):
CX Acidic pKa: 5.58CX Basic pKa: 10.01CX LogP: 2.35CX LogD: 2.35
Aromatic Rings: 3Heavy Atoms: 26QED Weighted: 0.57Np Likeness Score: -1.15

References

1. Enquist PA, Gylfe A, Hägglund U, Lindström P, Norberg-Scherman H, Sundin C, Elofsson M..  (2012)  Derivatives of 8-hydroxyquinoline--antibacterial agents that target intra- and extracellular Gram-negative pathogens.,  22  (10): [PMID:22525317] [10.1016/j.bmcl.2012.03.096]
2. Joaquim AR, Gionbelli MP, Gosmann G, Fuentefria AM, Lopes MS, Fernandes de Andrade S..  (2021)  Novel Antimicrobial 8-Hydroxyquinoline-Based Agents: Current Development, Structure-Activity Relationships, and Perspectives.,  64  (22.0): [PMID:34779640] [10.1021/acs.jmedchem.1c01318]

Source