ID: ALA603656

Max Phase: Preclinical

Molecular Formula: C23H25FN6O3

Molecular Weight: 452.49

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1cc(-c2nnn(C[C@H]3CC[C@H](C(=O)O)CC3)n2)cc(C(=O)NCc2ccc(F)cc2)n1

Standard InChI:  InChI=1S/C23H25FN6O3/c1-14-10-18(11-20(26-14)22(31)25-12-15-4-8-19(24)9-5-15)21-27-29-30(28-21)13-16-2-6-17(7-3-16)23(32)33/h4-5,8-11,16-17H,2-3,6-7,12-13H2,1H3,(H,25,31)(H,32,33)/t16-,17-

Standard InChI Key:  KOTGODCEORJYIF-QAQDUYKDSA-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: 452.49

Molecular Weight (Monoisotopic): 452.1972

AlogP: 3.00

#Rotatable Bonds: 7

Polar Surface Area: 122.89

Molecular Species: ACID

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 4.31

CX Basic pKa: 0.35

CX LogP: 3.71

CX LogD: 0.74

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.56

Np Likeness Score: -1.71

References

1. Schnute ME, O'Brien PM, Nahra J, Morris M, Howard Roark W, Hanau CE, Ruminski PG, Scholten JA, Fletcher TR, Hamper BC, Carroll JN, Patt WC, Shieh HS, Collins B, Pavlovsky AG, Palmquist KE, Aston KW, Hitchcock J, Rogers MD, McDonald J, Johnson AR, Munie GE, Wittwer AJ, Man CF, Settle SL, Nemirovskiy O, Vickery LE, Agawal A, Dyer RD, Sunyer T..  (2010)  Discovery of (pyridin-4-yl)-2H-tetrazole as a novel scaffold to identify highly selective matrix metalloproteinase-13 inhibitors for the treatment of osteoarthritis.,  20  (2): [PMID:20005097] [10.1016/j.bmcl.2009.11.081]

2. 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