2-(2,5-bis(4-(trifluoromethyl)benzyloxy)benzylidene)hexanoic acid

ID: ALA1819479

Chembl Id: CHEMBL1819479

PubChem CID: 53363314

Max Phase: Preclinical

Molecular Formula: C29H26F6O4

Molecular Weight: 552.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCC/C(=C\c1cc(OCc2ccc(C(F)(F)F)cc2)ccc1OCc1ccc(C(F)(F)F)cc1)C(=O)O

Standard InChI:  InChI=1S/C29H26F6O4/c1-2-3-4-21(27(36)37)15-22-16-25(38-17-19-5-9-23(10-6-19)28(30,31)32)13-14-26(22)39-18-20-7-11-24(12-8-20)29(33,34)35/h5-16H,2-4,17-18H2,1H3,(H,36,37)/b21-15+

Standard InChI Key:  KGYQXMLYIWZACL-RCCKNPSSSA-N

Alternative Forms

1. Parent:

   

   ALA1819479

   (2E)-2-[[2,5-bis[[4-(trifluoromethyl)phenyl]methoxy]phenyl]methylidene]hexanoic acid

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

Calculated Properties

Molecular Weight: 552.51

Molecular Weight (Monoisotopic): 552.1735

AlogP: 8.54

#Rotatable Bonds: 11

Polar Surface Area: 55.76

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 2

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 3.68

CX Basic pKa: ┄

CX LogP: 8.75

CX LogD: 5.44

Aromatic Rings: 3

Heavy Atoms: 39

QED Weighted: 0.19

Np Likeness Score: -0.20

References

1. Hieke M, Ness J, Steri R, Greiner C, Werz O, Schubert-Zsilavecz M, Weggen S, Zettl H..  (2011)  SAR studies of acidic dual γ-secretase/PPARγ modulators.,  19  (18): [PMID:21873070] [10.1016/j.bmc.2011.08.003]

2. Hieke M, Greiner C, Dittrich M, Reisen F, Schneider G, Schubert-Zsilavecz M, Werz O..  (2011)  Discovery and biological evaluation of a novel class of dual microsomal prostaglandin E2 synthase-1/5-lipoxygenase inhibitors based on 2-[(4,6-diphenethoxypyrimidin-2-yl)thio]hexanoic acid.,  54  (13): [PMID:21591611] [10.1021/jm200092b]

3. Flesch D, Ness J, Lamers C, Dehm F, Popella S, Steri R, Ogorek I, Hieke M, Dannhardt G, Werz O, Weggen S, Schubert-Zsilavecz M..  (2015)  SAR-studies of γ-secretase modulators with PPARγ-agonistic and 5-lipoxygenase-inhibitory activity for Alzheimer's disease.,  25  (4): [PMID:25575659] [10.1016/j.bmcl.2014.12.073]

Source

Source(1):

• Scientific Literature