ID: ALA5202896

Max Phase: Preclinical

Molecular Formula: C21H26F3N3O4

Molecular Weight: 441.45

Associated Items:

Representations

Canonical SMILES:  COC(=O)Nc1cc(-c2ccc(OC[C@@](C)(N)CC(C)C)c(OC(F)(F)F)c2)ccn1

Standard InChI:  InChI=1S/C21H26F3N3O4/c1-13(2)11-20(3,25)12-30-16-6-5-14(9-17(16)31-21(22,23)24)15-7-8-26-18(10-15)27-19(28)29-4/h5-10,13H,11-12,25H2,1-4H3,(H,26,27,28)/t20-/m0/s1

Standard InChI Key:  HAPXQAGUUXSYBV-FQEVSTJZSA-N

Associated Targets(Human)

Adaptor-associated kinase 1053 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Cytochrome P450 3A4 53859 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Associated Targets(non-human)

AP2-associated protein kinase 1 50 Activities

Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID

Molecule Features

Natural Product: NoOral: NoChemical Probe: NoParenteral: No
Molecule Type: Topical: 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

Properties

Molecular Weight: 441.45Molecular Weight (Monoisotopic): 441.1875AlogP: 4.97#Rotatable Bonds: 8
Polar Surface Area: 95.70Molecular Species: BASEHBA: 6HBD: 2
#RO5 Violations: 0HBA (Lipinski): 7HBD (Lipinski): 3#RO5 Violations (Lipinski): 0
CX Acidic pKa: 12.90CX Basic pKa: 9.80CX LogP: 5.28CX LogD: 2.97
Aromatic Rings: 2Heavy Atoms: 31QED Weighted: 0.60Np Likeness Score: -0.67

References

1. Luo G, Chen L, Kostich WA, Hamman B, Allen J, Easton A, Bourin C, Gulianello M, Lippy J, Nara S, Pattipati SN, Dandapani K, Dokania M, Vattikundala P, Sharma V, Elavazhagan S, Verma MK, Lal Das M, Wagh S, Balakrishnan A, Johnson BM, Santone KS, Thalody G, Denton R, Saminathan H, Holenarsipur VK, Kumar A, Rao A, Putlur SP, Sarvasiddhi SK, Shankar G, Louis JV, Ramarao M, Conway CM, Li YW, Pieschl R, Tian Y, Hong Y, Bristow L, Albright CF, Bronson JJ, Macor JE, Dzierba CD..  (2022)  Discovery and Optimization of Biaryl Alkyl Ethers as a Novel Class of Highly Selective, CNS-Penetrable, and Orally Active Adaptor Protein-2-Associated Kinase 1 (AAK1) Inhibitors for the Potential Treatment of Neuropathic Pain.,  65  (6.0): [PMID:35261239] [10.1021/acs.jmedchem.1c02132]

Source