ID: ALA270050

Max Phase: Preclinical

Molecular Formula: C24H20N4O5

Molecular Weight: 444.45

Molecule Type: Small molecule

Representations

Canonical SMILES:  COc1ccc(CNC(=O)c2cc3c(=O)n(Cc4ccc(C(=O)O)cc4)cnc3cn2)cc1

Standard InChI:  InChI=1S/C24H20N4O5/c1-33-18-8-4-15(5-9-18)11-26-22(29)20-10-19-21(12-25-20)27-14-28(23(19)30)13-16-2-6-17(7-3-16)24(31)32/h2-10,12,14H,11,13H2,1H3,(H,26,29)(H,31,32)

Standard InChI Key:  YOFJHCFIKFPSLE-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: 444.45

Molecular Weight (Monoisotopic): 444.1434

AlogP: 2.48

#Rotatable Bonds: 7

Polar Surface Area: 123.41

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 4.07

CX Basic pKa: 2.10

CX LogP: 2.05

CX LogD: -0.98

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.45

Np Likeness Score: -1.04

References

1. Li JJ, Nahra J, Johnson AR, Bunker A, O'Brien P, Yue WS, Ortwine DF, Man CF, Baragi V, Kilgore K, Dyer RD, Han HK..  (2008)  Quinazolinones and pyrido[3,4-d]pyrimidin-4-ones as orally active and specific matrix metalloproteinase-13 inhibitors for the treatment of osteoarthritis.,  51  (4): [PMID:18251495] [10.1021/jm701274v]

2. Georgiadis D, Yiotakis A..  (2008)  Specific targeting of metzincin family members with small-molecule inhibitors: progress toward a multifarious challenge.,  16  (19): [PMID:18790648] [10.1016/j.bmc.2008.08.058]

3. Ruminski PG, Massa M, Strohbach J, Hanau CE, Schmidt M, Scholten JA, Fletcher TR, Hamper BC, Carroll JN, Shieh HS, Caspers N, Collins B, Grapperhaus M, Palmquist KE, Collins J, Baldus JE, Hitchcock J, Kleine HP, Rogers MD, McDonald J, Munie GE, Messing DM, Portolan S, Whiteley LO, Sunyer T, Schnute ME..  (2016)  Discovery of N-(4-Fluoro-3-methoxybenzyl)-6-(2-(((2S,5R)-5-(hydroxymethyl)-1,4-dioxan-2-yl)methyl)-2H-tetrazol-5-yl)-2-methylpyrimidine-4-carboxamide. A Highly Selective and Orally Bioavailable Matrix Metalloproteinase-13 Inhibitor for the Potential Treatment of Osteoarthritis.,  59  (1): [PMID:26653735] [10.1021/acs.jmedchem.5b01434]

Source

Source(1):

• Scientific Literature