ID: ALA5185000

Max Phase: Preclinical

Molecular Formula: C20H25N5O3

Molecular Weight: 383.45

Representations

Canonical SMILES:  COC(=O)Nc1cc(-c2cnc(OC[C@@](C)(N)CC(C)C)c(C#N)c2)ccn1

Standard InChI:  InChI=1S/C20H25N5O3/c1-13(2)9-20(3,22)12-28-18-15(10-21)7-16(11-24-18)14-5-6-23-17(8-14)25-19(26)27-4/h5-8,11,13H,9,12,22H2,1-4H3,(H,23,25,26)/t20-/m0/s1

Standard InChI Key:  HDBIRBUHIXXLDF-FQEVSTJZSA-N

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Properties

Molecular Weight: 383.45

Molecular Weight (Monoisotopic): 383.1957

AlogP: 3.34

#Rotatable Bonds: 7

Polar Surface Area: 123.15

Molecular Species: BASE

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 12.89

CX Basic pKa: 9.80

CX LogP: 3.08

CX LogD: 0.78

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.75

Np Likeness Score: -0.91

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

Source(1):

• Scientific Literature