ID: ALA253237

Max Phase: Preclinical

Molecular Formula: C27H23ClN4O3

Molecular Weight: 486.96

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC(=O)c1ccc(Oc2ccc(-c3ccc(-c4ccccc4Cl)n3CC(=O)NC(=N)N)cc2)cc1

Standard InChI:  InChI=1S/C27H23ClN4O3/c1-17(33)18-6-10-20(11-7-18)35-21-12-8-19(9-13-21)24-14-15-25(22-4-2-3-5-23(22)28)32(24)16-26(34)31-27(29)30/h2-15H,16H2,1H3,(H4,29,30,31,34)

Standard InChI Key:  MIEKBLPHNQZVQQ-UHFFFAOYSA-N

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

Properties

Molecular Weight: 486.96

Molecular Weight (Monoisotopic): 486.1459

AlogP: 5.48

#Rotatable Bonds: 7

Polar Surface Area: 110.20

Molecular Species: BASE

HBA: 5

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.45

CX Basic pKa: 8.59

CX LogP: 4.47

CX LogD: 3.28

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.18

Np Likeness Score: -0.80

References

1. Cole DC, Manas ES, Stock JR, Condon JS, Jennings LD, Aulabaugh A, Chopra R, Cowling R, Ellingboe JW, Fan KY, Harrison BL, Hu Y, Jacobsen S, Jin G, Lin L, Lovering FE, Malamas MS, Stahl ML, Strand J, Sukhdeo MN, Svenson K, Turner MJ, Wagner E, Wu J, Zhou P, Bard J..  (2006)  Acylguanidines as small-molecule beta-secretase inhibitors.,  49  (21): [PMID:17034121] [10.1021/jm0607451]

2. Cole DC, Stock JR, Chopra R, Cowling R, Ellingboe JW, Fan KY, Harrison BL, Hu Y, Jacobsen S, Jennings LD, Jin G, Lohse PA, Malamas MS, Manas ES, Moore WJ, O'Donnell MM, Olland AM, Robichaud AJ, Svenson K, Wu J, Wagner E, Bard J..  (2008)  Acylguanidine inhibitors of beta-secretase: optimization of the pyrrole ring substituents extending into the S1 and S3 substrate binding pockets.,  18  (3): [PMID:18162398] [10.1016/j.bmcl.2007.12.010]

3. Jennings LD, Cole DC, Stock JR, Sukhdeo MN, Ellingboe JW, Cowling R, Jin G, Manas ES, Fan KY, Malamas MS, Harrison BL, Jacobsen S, Chopra R, Lohse PA, Moore WJ, O'Donnell MM, Hu Y, Robichaud AJ, Turner MJ, Wagner E, Bard J..  (2008)  Acylguanidine inhibitors of beta-secretase: optimization of the pyrrole ring substituents extending into the S1' substrate binding pocket.,  18  (2): [PMID:18068983] [10.1016/j.bmcl.2007.11.043]

Source

Source(1):

• Scientific Literature