ID: ALA217068

Max Phase: Preclinical

Molecular Formula: C19H18N4O

Molecular Weight: 318.38

Molecule Type: Small molecule

Representations

Canonical SMILES:  N=C(N)NC(=O)Cn1c(-c2ccccc2)ccc1-c1ccccc1

Standard InChI:  InChI=1S/C19H18N4O/c20-19(21)22-18(24)13-23-16(14-7-3-1-4-8-14)11-12-17(23)15-9-5-2-6-10-15/h1-12H,13H2,(H4,20,21,22,24)

Standard InChI Key:  WVLDNAVUCUAGDP-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: 318.38

Molecular Weight (Monoisotopic): 318.1481

AlogP: 2.83

#Rotatable Bonds: 4

Polar Surface Area: 83.90

Molecular Species: BASE

HBA: 3

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.30

CX Basic pKa: 8.79

CX LogP: 2.81

CX LogD: 1.44

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.51

Np Likeness Score: -0.68

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. Fobare WF, Solvibile WR, Robichaud AJ, Malamas MS, Manas E, Turner J, Hu Y, Wagner E, Chopra R, Cowling R, Jin G, Bard J..  (2007)  Thiophene substituted acylguanidines as BACE1 inhibitors.,  17  (19): [PMID:17761418] [10.1016/j.bmcl.2007.08.010]

3. 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]

4. 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]

5. Nowak P, Cole DC, Aulabaugh A, Bard J, Chopra R, Cowling R, Fan KY, Hu B, Jacobsen S, Jani M, Jin G, Lo MC, Malamas MS, Manas ES, Narasimhan R, Reinhart P, Robichaud AJ, Stock JR, Subrath J, Svenson K, Turner J, Wagner E, Zhou P, Ellingboe JW..  (2010)  Discovery and initial optimization of 5,5'-disubstituted aminohydantoins as potent beta-secretase (BACE1) inhibitors.,  20  (2): [PMID:19959359] [10.1016/j.bmcl.2009.11.052]

Source

Source(1):

• Scientific Literature