ID: ALA1668934

Max Phase: Preclinical

Molecular Formula: C15H18F3N3O3

Molecular Weight: 345.32

Molecule Type: Small molecule

Representations

Canonical SMILES:  CC(=O)N1CCC(NC(=O)Nc2ccc(OC(F)(F)F)cc2)CC1

Standard InChI:  InChI=1S/C15H18F3N3O3/c1-10(22)21-8-6-12(7-9-21)20-14(23)19-11-2-4-13(5-3-11)24-15(16,17)18/h2-5,12H,6-9H2,1H3,(H2,19,20,23)

Standard InChI Key:  UAKAZEQUWPXSOS-UHFFFAOYSA-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: 345.32

Molecular Weight (Monoisotopic): 345.1300

AlogP: 2.72

#Rotatable Bonds: 3

Polar Surface Area: 70.67

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.90

CX Basic pKa:

CX LogP: 1.79

CX LogD: 1.79

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.88

Np Likeness Score: -1.75

References

1. Anandan SK, Webb HK, Chen D, Wang YX, Aavula BR, Cases S, Cheng Y, Do ZN, Mehra U, Tran V, Vincelette J, Waszczuk J, White K, Wong KR, Zhang LN, Jones PD, Hammock BD, Patel DV, Whitcomb R, MacIntyre DE, Sabry J, Gless R..  (2011)  1-(1-acetyl-piperidin-4-yl)-3-adamantan-1-yl-urea (AR9281) as a potent, selective, and orally available soluble epoxide hydrolase inhibitor with efficacy in rodent models of hypertension and dysglycemia.,  21  (3): [PMID:21211973] [10.1016/j.bmcl.2010.12.042]

2. Lee KS, Liu JY, Wagner KM, Pakhomova S, Dong H, Morisseau C, Fu SH, Yang J, Wang P, Ulu A, Mate CA, Nguyen LV, Hwang SH, Edin ML, Mara AA, Wulff H, Newcomer ME, Zeldin DC, Hammock BD..  (2014)  Optimized inhibitors of soluble epoxide hydrolase improve in vitro target residence time and in vivo efficacy.,  57  (16): [PMID:25079952] [10.1021/jm500694p]

3.  (2013)  Conformationally restricted urea inhibitors of soluble epoxide hydrolase, 

4. Codony S, Pont C, Griñán-Ferré C, Di Pede-Mattatelli A, Calvó-Tusell C, Feixas F, Osuna S, Jarné-Ferrer J, Naldi M, Bartolini M, Loza MI, Brea J, Pérez B, Bartra C, Sanfeliu C, Juárez-Jiménez J, Morisseau C, Hammock BD, Pallàs M, Vázquez S, Muñoz-Torrero D..  (2022)  Discovery and In Vivo Proof of Concept of a Highly Potent Dual Inhibitor of Soluble Epoxide Hydrolase and Acetylcholinesterase for the Treatment of Alzheimer's Disease.,  65  (6.0): [PMID:35271276] [10.1021/acs.jmedchem.1c02150]

Source

Source(2):

• Scientific Literature
• BindingDB Database