3-(4-chloropyridin-2-yl)-1'-(4-(trifluoromethoxy)benzyl)-3H-spiro[isobenzofuran-1,4'-piperidine]

ID: ALA1951465

Chembl Id: CHEMBL1951465

PubChem CID: 54577783

Max Phase: Preclinical

Molecular Formula: C25H22ClF3N2O2

Molecular Weight: 474.91

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  FC(F)(F)Oc1ccc(CN2CCC3(CC2)OC(c2cc(Cl)ccn2)c2ccccc23)cc1

Standard InChI:  InChI=1S/C25H22ClF3N2O2/c26-18-9-12-30-22(15-18)23-20-3-1-2-4-21(20)24(33-23)10-13-31(14-11-24)16-17-5-7-19(8-6-17)32-25(27,28)29/h1-9,12,15,23H,10-11,13-14,16H2

Standard InChI Key:  LFFCKQUVNSOFQR-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1951465

   Benzodihydroisofuran derivative 1

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: 474.91

Molecular Weight (Monoisotopic): 474.1322

AlogP: 6.24

#Rotatable Bonds: 4

Polar Surface Area: 34.59

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 8.41

CX LogP: 6.11

CX LogD: 5.06

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.45

Np Likeness Score: -0.76

References

1. Shen HC, Ding FX, Jiang J, Verras A, Chabin RM, Xu S, Tong X, Chen Q, Xie D, Lassman ME, Bhatt UR, Garcia-Calvo MM, Geissler W, Shen Z, Murphy BA, Gorski JN, Wiltsie J, SinhaRoy R, Hale JJ, Pinto S, Shen DM..  (2012)  Discovery of benzodihydroisofurans as novel, potent, bioavailable and brain-penetrant prolylcarboxypeptidase inhibitors.,  22  (4): [PMID:22264488] [10.1016/j.bmcl.2012.01.002]

2.  (2014)  Spiropiperidine prolylcarboxypeptidase inhibitors, 

Source

Source(2):

• Scientific Literature
• BindingDB Database