ID: ALA325163

Max Phase: Preclinical

Molecular Formula: C34H42F3N5O8

Molecular Weight: 705.73

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C1NCCCC[C@@H](C(=O)NCC(=O)N2CCOCC2)NC(=O)[C@H](Cc2ccc(-c3ccccc3C(F)(F)F)cc2)[C@@H](C(=O)NO)CCCO1

Standard InChI:  InChI=1S/C34H42F3N5O8/c35-34(36,37)27-8-2-1-6-24(27)23-12-10-22(11-13-23)20-26-25(31(45)41-48)7-5-17-50-33(47)38-14-4-3-9-28(40-30(26)44)32(46)39-21-29(43)42-15-18-49-19-16-42/h1-2,6,8,10-13,25-26,28,48H,3-5,7,9,14-21H2,(H,38,47)(H,39,46)(H,40,44)(H,41,45)/t25-,26+,28-/m0/s1

Standard InChI Key:  RWKJBOMUESGCBO-REUBFRLUSA-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: 705.73

Molecular Weight (Monoisotopic): 705.2985

AlogP: 2.80

#Rotatable Bonds: 7

Polar Surface Area: 175.40

Molecular Species: NEUTRAL

HBA: 8

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 8.86

CX Basic pKa:

CX LogP: 2.04

CX LogD: 2.02

Aromatic Rings: 2

Heavy Atoms: 50

QED Weighted: 0.22

Np Likeness Score: -0.51

References

1. Xue CB, He X, Corbett RL, Roderick J, Wasserman ZR, Liu RQ, Jaffee BD, Covington MB, Qian M, Trzaskos JM, Newton RC, Magolda RL, Wexler RR, Decicco CP..  (2001)  Discovery of macrocyclic hydroxamic acids containing biphenylmethyl derivatives at P1', a series of selective TNF-alpha converting enzyme inhibitors with potent cellular activity in the inhibition of TNF-alpha release.,  44  (21): [PMID:11585440] [10.1021/jm0155502]

2. Xue CB, He X, Roderick J, Corbett RL, Duan JJ, Liu RQ, Covington MB, Newton RC, Trzaskos JM, Magolda RL, Wexler RR, Decicco CP..  (2003)  Rational design, synthesis and structure-activity relationships of a cyclic succinate series of TNF-alpha converting enzyme inhibitors. Part 1: lead identification.,  13  (24): [PMID:14643312] [10.1016/j.bmcl.2003.09.056]

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