(1R,2R,3R)-2-(4-(5-Fluoropyrimidin-2-yl)phenyl)-N-hydroxy-3-phenylcyclopropanecarboxamide

ID: ALA3110015

Chembl Id: CHEMBL3110015

PubChem CID: 60148711

Max Phase: Preclinical

Molecular Formula: C20H16FN3O2

Molecular Weight: 349.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NO)[C@@H]1[C@H](c2ccccc2)[C@H]1c1ccc(-c2ncc(F)cn2)cc1

Standard InChI:  InChI=1S/C20H16FN3O2/c21-15-10-22-19(23-11-15)14-8-6-13(7-9-14)17-16(18(17)20(25)24-26)12-4-2-1-3-5-12/h1-11,16-18,26H,(H,24,25)/t16-,17-,18-/m1/s1

Standard InChI Key:  QHCRWOYXPXJUJS-KZNAEPCWSA-N

Alternative Forms

1. Parent:

   

   ALA3110015

   (1r,2r,3r)-2-[4-(5-Fluoranylpyrimidin-2-Yl)phenyl]-N-Oxidanyl-3-Phenyl-Cyclopropane-1-Carboxamide

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: 349.37

Molecular Weight (Monoisotopic): 349.1227

AlogP: 3.29

#Rotatable Bonds: 4

Polar Surface Area: 75.11

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 8.86

CX Basic pKa: 0.08

CX LogP: 3.11

CX LogD: 3.10

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.56

Np Likeness Score: -0.54

References

1. Bürli RW, Luckhurst CA, Aziz O, Matthews KL, Yates D, Lyons KA, Beconi M, McAllister G, Breccia P, Stott AJ, Penrose SD, Wall M, Lamers M, Leonard P, Müller I, Richardson CM, Jarvis R, Stones L, Hughes S, Wishart G, Haughan AF, O'Connell C, Mead T, McNeil H, Vann J, Mangette J, Maillard M, Beaumont V, Munoz-Sanjuan I, Dominguez C..  (2013)  Design, synthesis, and biological evaluation of potent and selective class IIa histone deacetylase (HDAC) inhibitors as a potential therapy for Huntington's disease.,  56  (24): [PMID:24261862] [10.1021/jm4011884]

2. Luckhurst CA, Breccia P, Stott AJ, Aziz O, Birch HL, Bürli RW, Hughes SJ, Jarvis RE, Lamers M, Leonard PM, Matthews KL, McAllister G, Pollack S, Saville-Stones E, Wishart G, Yates D, Dominguez C..  (2016)  Potent, Selective, and CNS-Penetrant Tetrasubstituted Cyclopropane Class IIa Histone Deacetylase (HDAC) Inhibitors.,  7  (1): [PMID:26819662] [10.1021/acsmedchemlett.5b00302]

Source

Source(1):

• Scientific Literature