ID: ALA293277

Max Phase: Preclinical

Molecular Formula: C8H5F3O

Molecular Weight: 174.12

Molecule Type: Small molecule

Representations

Canonical SMILES:  O=C(c1ccccc1)C(F)(F)F

Standard InChI:  InChI=1S/C8H5F3O/c9-8(10,11)7(12)6-4-2-1-3-5-6/h1-5H

Standard InChI Key:  KZJRKRQSDZGHEC-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: 174.12

Molecular Weight (Monoisotopic): 174.0292

AlogP: 2.43

#Rotatable Bonds: 1

Polar Surface Area: 17.07

Molecular Species:

HBA: 1

HBD: 0

#RO5 Violations: 0

HBA (Lipinski): 1

HBD (Lipinski): 0

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 2.66

CX LogD: 2.66

Aromatic Rings: 1

Heavy Atoms: 12

QED Weighted: 0.60

Np Likeness Score: -0.69

References

1. Kawase M, Harada H, Saito S, Cui J, Tani S..  (1999)  In vitro susceptibility of Helicobacter pylori to trifluoromethyl ketones.,  9  (2): [PMID:10021926] [10.1016/s0960-894x(98)00726-4]

2. Duran I, Parrilla A, Feixas J, Guerrero A.  (1993)  Inhibition of antennal esterases of the egyptian armyworm Spodoptera littoralis by trifluoromethyl ketones,  3  (12): [10.1016/S0960-894X(01)80722-8]

3. Kawase M, Sakagami H, Kusama K, Motohashi N, Saito S..  (1999)  Alpha-trifluoromethylated acyloins induce apoptosis in human oral tumor cell lines.,  9  (21): [PMID:10560735] [10.1016/s0960-894x(99)00548-x]

4. Hamada H, Nakajima N, Shisa Y, Funahashi M, Nakamura K.  (1994)  Enantioselective reduction of ethyl 3-methyl-2-oxobutanoate by an enzymatic system from callus of catharanthus roseus,  4  (7): [10.1016/S0960-894X(01)80261-4]

5. Boger DL, Miyauchi H, Du W, Hardouin C, Fecik RA, Cheng H, Hwang I, Hedrick MP, Leung D, Acevedo O, Guimarães CR, Jorgensen WL, Cravatt BF..  (2005)  Discovery of a potent, selective, and efficacious class of reversible alpha-ketoheterocycle inhibitors of fatty acid amide hydrolase effective as analgesics.,  48  (6): [PMID:15771430] [10.1021/jm049614v]

6. Wheelock CE, Nakagawa Y, Akamatsu M, Hammock BD..  (2003)  Use of classical and 3-D QSAR to examine the hydration state of juvenile hormone esterase inhibitors.,  11  (23): [PMID:14604674] [10.1016/j.bmc.2003.08.023]

7. Depetter Y, Geurs S, Vanden Bussche F, De Vreese R, Franceus J, Desmet T, De Wever O, D'hooghe M..  (2018)  Assessment of the trifluoromethyl ketone functionality as an alternative zinc-binding group for selective HDAC6 inhibition.,  9  (6): [PMID:30108990] [10.1039/C8MD00107C]

8. Martin JS, MacKenzie CJ, Fletcher D, Gilbert IH..  (2019)  Characterising covalent warhead reactivity.,  27  (10): [PMID:30975501] [10.1016/j.bmc.2019.04.002]

9. Madden KS, Todd PMT, Urata K, Russell AJ, Vincent KA, Reeve HA..  (2023)  A pharmacophore-based approach to demonstrating the scope of alcohol dehydrogenases.,  83  [PMID:36966660] [10.1016/j.bmc.2023.117255]

Source

Source(1):

• Scientific Literature