ID: ALA207305

Max Phase: Preclinical

Molecular Formula: C25H27N3O5

Molecular Weight: 449.51

Molecule Type: Small molecule

Representations

Canonical SMILES:  Cc1cc(COc2ccc(C(=O)NC3(CC(=O)NO)CCOCC3)cc2)c2ccccc2n1

Standard InChI:  InChI=1S/C25H27N3O5/c1-17-14-19(21-4-2-3-5-22(21)26-17)16-33-20-8-6-18(7-9-20)24(30)27-25(15-23(29)28-31)10-12-32-13-11-25/h2-9,14,31H,10-13,15-16H2,1H3,(H,27,30)(H,28,29)

Standard InChI Key:  NUVSGXIVCJBRBF-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: 449.51

Molecular Weight (Monoisotopic): 449.1951

AlogP: 3.30

#Rotatable Bonds: 7

Polar Surface Area: 109.78

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: 0

HBA (Lipinski): 8

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.89

CX Basic pKa: 5.02

CX LogP: 1.69

CX LogD: 1.68

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.38

Np Likeness Score: -0.91

References

1. Gilmore JL, King BW, Harris C, Maduskuie T, Mercer SE, Liu RQ, Covington MB, Qian M, Ribadeneria MD, Vaddi K, Trzaskos JM, Newton RC, Decicco CP, Duan JJ..  (2006)  Synthesis and structure-activity relationship of a novel, achiral series of TNF-alpha converting enzyme inhibitors.,  16  (10): [PMID:16516466] [10.1016/j.bmcl.2006.02.015]

2. DasGupta S, Murumkar PR, Giridhar R, Yadav MR..  (2009)  Current perspective of TACE inhibitors: a review.,  17  (2): [PMID:19095454] [10.1016/j.bmc.2008.11.067]

3. 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]

Source

Source(1):

• Scientific Literature