9,9,9-Trifluoro-8-oxo-nonanoic acid phenylamide

ID: ALA113537

Chembl Id: CHEMBL113537

PubChem CID: 9882812

Max Phase: Preclinical

Molecular Formula: C15H18F3NO2

Molecular Weight: 301.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(CCCCCCC(=O)C(F)(F)F)Nc1ccccc1

Standard InChI:  InChI=1S/C15H18F3NO2/c16-15(17,18)13(20)10-6-1-2-7-11-14(21)19-12-8-4-3-5-9-12/h3-5,8-9H,1-2,6-7,10-11H2,(H,19,21)

Standard InChI Key:  KRCXZGYVOZSCSF-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA113537

   9,9,9-Trifluoro-8-Oxo-N-Phenylnonanamide

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: 301.31

Molecular Weight (Monoisotopic): 301.1290

AlogP: 4.10

#Rotatable Bonds: 8

Polar Surface Area: 46.17

Molecular Species: NEUTRAL

HBA: 2

HBD: 1

#RO5 Violations: 0

HBA (Lipinski): 3

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 0

CX Acidic pKa:

CX Basic pKa:

CX LogP: 4.28

CX LogD: 4.28

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.73

Np Likeness Score: -0.83

References

1. Suzuki T, Kouketsu A, Matsuura A, Kohara A, Ninomiya S, Kohda K, Miyata N..  (2004)  Thiol-based SAHA analogues as potent histone deacetylase inhibitors.,  14  (12): [PMID:15149697] [10.1016/j.bmcl.2004.03.063]

2. Frey RR, Wada CK, Garland RB, Curtin ML, Michaelides MR, Li J, Pease LJ, Glaser KB, Marcotte PA, Bouska JJ, Murphy SS, Davidsen SK..  (2002)  Trifluoromethyl ketones as inhibitors of histone deacetylase.,  12  (23): [PMID:12419380] [10.1016/s0960-894x(02)00754-0]

3. Miller TA, Witter DJ, Belvedere S..  (2003)  Histone deacetylase inhibitors.,  46  (24): [PMID:14613312] [10.1021/jm0303094]

4. Ilies M, Dowling DP, Lombardi PM, Christianson DW..  (2011)  Synthesis of a new trifluoromethylketone analogue of l-arginine and contrasting inhibitory activity against human arginase I and histone deacetylase 8.,  21  (19): [PMID:21875805] [10.1016/j.bmcl.2011.07.100]

5. Madsen AS, Olsen CA.  (2016)  A potent trifluoromethyl ketone histone deacetylase inhibitor exhibits class-dependent mechanism of action,  7  (3): [10.1039/C5MD00451A]

6. Ramesh R, Reddy DS..  (2018)  Quest for Novel Chemical Entities through Incorporation of Silicon in Drug Scaffolds.,  61  (9): [PMID:29039662] [10.1021/acs.jmedchem.7b00718]

7. Riddhidev B, Endri K, Sabitri L, Kotsull Lauren N, Nishanth K, Dragan I, Mary Kay H P, James S, William T, L M Viranga T..  (2022)  Rational design of metabolically stable HDAC inhibitors: An overhaul of trifluoromethyl ketones.,  244  [PMID:36244186] [10.1016/j.ejmech.2022.114807]

Source

Source(1):

• Scientific Literature