4-Furan-3-yl-7-[3-(3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-3-yl)-benzyloxy]-naphthalene-2-carbonitrile

ID: ALA97380

Chembl Id: CHEMBL97380

PubChem CID: 44329500

Max Phase: Preclinical

Molecular Formula: C28H23NO5

Molecular Weight: 453.49

Molecule Type: Small molecule

Associated Items:

Names and Identifiers

Canonical SMILES:  N#Cc1cc(-c2ccoc2)c2ccc(OCc3cccc(C4(O)CC5COC(C4)O5)c3)cc2c1

Standard InChI:  InChI=1S/C28H23NO5/c29-14-19-8-21-11-23(4-5-25(21)26(10-19)20-6-7-31-16-20)32-15-18-2-1-3-22(9-18)28(30)12-24-17-33-27(13-28)34-24/h1-11,16,24,27,30H,12-13,15,17H2

Standard InChI Key:  CHLJRXIFRPILDX-UHFFFAOYSA-N

Associated Targets(Human)

ALOX5 Tclin Arachidonate 5-lipoxygenase (6568 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Homo sapiens (32628 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

Rattus norvegicus (775804 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: 453.49Molecular Weight (Monoisotopic): 453.1576AlogP: 5.27#Rotatable Bonds: 5
Polar Surface Area: 84.85Molecular Species: NEUTRALHBA: 6HBD: 1
#RO5 Violations: 1HBA (Lipinski): 6HBD (Lipinski): 1#RO5 Violations (Lipinski): 1
CX Acidic pKa: 13.80CX Basic pKa: CX LogP: 4.67CX LogD: 4.67
Aromatic Rings: 4Heavy Atoms: 34QED Weighted: 0.44Np Likeness Score: 0.23

References

1. Hamel P, Riendeau D, Brideau C, Chan CC, Desmarais S, Delorme D, Dubé D, Ducharme Y, Ethier D, Grimm E, Falgueyret JP, Guay J, Jones TR, Kwong E, McAuliffe M, McFarlane CS, Piechuta H, Roumi M, Tagari P, Young RN, Girard Y..  (1997)  Substituted (pyridylmethoxy)naphthalenes as potent and orally active 5-lipoxygenase inhibitors; synthesis, biological profile, and pharmacokinetics of L-739,010.,  40  (18): [PMID:9288168] [10.1021/jm970046b]
2. Delorme D, Ducharme Y, Brideau C, Chan CC, Chauret N, Desmarais S, Dubé D, Falgueyret JP, Fortin R, Guay J, Hamel P, Jones TR, Lépine C, Li C, McAuliffe M, McFarlane CS, Nicoll-Griffith DA, Riendeau D, Yergey JA, Girard Y..  (1996)  Dioxabicyclooctanyl naphthalenenitriles as nonredox 5-lipoxygenase inhibitors: structure-activity relationship study directed toward the improvement of metabolic stability.,  39  (20): [PMID:8831761] [10.1021/jm960301c]
3. Wu YJ, Meanwell NA..  (2021)  Geminal Diheteroatomic Motifs: Some Applications of Acetals, Ketals, and Their Sulfur and Nitrogen Homologues in Medicinal Chemistry and Drug Design.,  64  (14.0): [PMID:34213340] [10.1021/acs.jmedchem.1c00790]

Source