ID: ALA3100015

Max Phase: Preclinical

Molecular Formula: C21H20F6N2O3

Molecular Weight: 462.39

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(Nc1cccc(C(F)(F)F)c1)N[C@H]1CC[C@H](Oc2ccc(OC(F)(F)F)cc2)CC1

Standard InChI:  InChI=1S/C21H20F6N2O3/c22-20(23,24)13-2-1-3-15(12-13)29-19(30)28-14-4-6-16(7-5-14)31-17-8-10-18(11-9-17)32-21(25,26)27/h1-3,8-12,14,16H,4-7H2,(H2,28,29,30)/t14-,16-

Standard InChI Key:  SHLYFOJAJRGKND-KOMQPUFPSA-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: 462.39

Molecular Weight (Monoisotopic): 462.1378

AlogP: 6.12

#Rotatable Bonds: 5

Polar Surface Area: 59.59

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 13.30

CX Basic pKa:

CX LogP: 6.16

CX LogD: 6.16

Aromatic Rings: 2

Heavy Atoms: 32

QED Weighted: 0.53

Np Likeness Score: -1.25

References

1. Chen T, Takrouri K, Hee-Hwang S, Rana S, Yefidoff-Freedman R, Halperin J, Natarajan A, Morisseau C, Hammock B, Chorev M, Aktas BH..  (2013)  Explorations of substituted urea functionality for the discovery of new activators of the heme-regulated inhibitor kinase.,  56  (23): [PMID:24261904] [10.1021/jm400793v]

2. Yefidoff-Freedman R, Fan J, Yan L, Zhang Q, Dos Santos GRR, Rana S, Contreras JI, Sahoo R, Wan D, Young J, Dias Teixeira KL, Morisseau C, Halperin J, Hammock B, Natarajan A, Wang P, Chorev M, Aktas BH..  (2017)  Development of 1-((1,4-trans)-4-Aryloxycyclohexyl)-3-arylurea Activators of Heme-Regulated Inhibitor as Selective Activators of the Eukaryotic Initiation Factor 2 Alpha (eIF2α) Phosphorylation Arm of the Integrated Endoplasmic Reticulum Stress Response.,  60  (13): [PMID:28590739] [10.1021/acs.jmedchem.7b00059]

Source

Source(1):

• Scientific Literature