1,1,1-Trifluoro-3-octylsulfanyl-propan-2-one

ID: ALA89506

Chembl Id: CHEMBL89506

Cas Number: 89820-00-8

PubChem CID: 146089

Max Phase: Preclinical

Molecular Formula: C11H19F3OS

Molecular Weight: 256.33

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C11H19F3OS/c1-2-3-4-5-6-7-8-16-9-10(15)11(12,13)14/h2-9H2,1H3

Standard InChI Key:  WMQHRXUKAYSPPK-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA89506

   3-Octylthio-1,1,1-trifluoro-2-propanone

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: 256.33

Molecular Weight (Monoisotopic): 256.1109

AlogP: 4.21

#Rotatable Bonds: 9

Polar Surface Area: 17.07

Molecular Species: NEUTRAL

HBA: 2

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 1

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.86

CX Basic pKa: ┄

CX LogP: 4.85

CX LogD: 4.85

Aromatic Rings: ┄

Heavy Atoms: 16

QED Weighted: 0.57

Np Likeness Score: -0.60

References

1. 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]

2. Wheelock CE, Nishi K, Ying A, Jones PD, Colvin ME, Olmstead MM, Hammock BD..  (2008)  Influence of sulfur oxidation state and steric bulk upon trifluoromethyl ketone (TFK) binding kinetics to carboxylesterases and fatty acid amide hydrolase (FAAH).,  16  (4): [PMID:18023188] [10.1016/j.bmc.2007.10.081]

3. Harada T, Nakagawa Y, Wadkins RM, Potter PM, Wheelock CE..  (2009)  Comparison of benzil and trifluoromethyl ketone (TFK)-mediated carboxylesterase inhibition using classical and 3D-quantitative structure-activity relationship analysis.,  17  (1): [PMID:19062296] [10.1016/j.bmc.2008.11.008]

4. Wheelock CE, Severson TF, Hammock BD..  (2001)  Synthesis of new carboxylesterase inhibitors and evaluation of potency and water solubility.,  14  (12): [PMID:11743738] [10.1021/tx015508+]

5. Muñoz L, Bosch MP, Batllori L, Rosell G, Bosch D, Guerrero A, Avilla J..  (2011)  Synthesis of allylic trifluoromethyl ketones and their activity as inhibitors of the sex pheromone of the leopard moth, Zeuzera pyrina L. (Lepidoptera: Cossidae).,  67  (8): [PMID:21394886] [10.1002/ps.2139]

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. Mouchlis VD, Armando A, Dennis EA..  (2019)  Substrate-Specific Inhibition Constants for Phospholipase A₂ Acting on Unique Phospholipid Substrates in Mixed Micelles and Membranes Using Lipidomics.,  62  (4): [PMID:30615445] [10.1021/acs.jmedchem.8b01568]

8. Mouchlis VD, Morisseau C, Hammock BD, Li S, McCammon JA, Dennis EA..  (2016)  Computer-aided drug design guided by hydrogen/deuterium exchange mass spectrometry: A powerful combination for the development of potent and selective inhibitors of Group VIA calcium-independent phospholipase A₂.,  24  (20): [PMID:27320659] [10.1016/j.bmc.2016.05.009]

Source

Source(1):

• Scientific Literature