4-Acetyl-5-cyclohexyl-3-hydroxy-1-(3-(trifluoromethyl)phenyl)-1,5-dihydro-2H-pyrrol-2-one

ID: ALA4483756

PubChem CID: 155540563

Max Phase: Preclinical

Molecular Formula: C19H20F3NO3

Molecular Weight: 367.37

Molecule Type: Unknown

This compound is available for customization.

Associated Items:

Bioactivity Summary Target Summary Assay Summary

Names and Identifiers

Canonical SMILES: CC(=O)C1=C(O)C(=O)N(c2cccc(C(F)(F)F)c2)C1C1CCCCC1

Standard InChI: InChI=1S/C19H20F3NO3/c1-11(24)15-16(12-6-3-2-4-7-12)23(18(26)17(15)25)14-9-5-8-13(10-14)19(20,21)22/h5,8-10,12,16,25H,2-4,6-7H2,1H3

Standard InChI Key: CBIIFLNUGQBIPM-UHFFFAOYSA-N

Molfile:

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   12.0790  -10.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0778  -10.9972    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7859  -11.4062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4955  -10.9968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4927  -10.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7841   -9.7688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3692  -12.2225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3679  -11.4091    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.5939  -11.1588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1168  -11.8177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5959  -12.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0310  -12.7018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3446  -13.2525    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.2996  -11.8189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8921  -12.5272    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3403  -10.3820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8881   -9.7773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6374   -9.0033    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8384   -8.8303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2903   -9.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5414  -10.2183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8899  -11.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7817   -8.9517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4881   -8.5410    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.0727   -8.5452    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.7738   -8.1306    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  8  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11  7  1  0
  7 12  2  0
 11 13  1  0
 10 14  1  0
 14 15  2  0
  9 16  1  0
 16 17  1  0
 16 21  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 14 22  1  0
  6 23  1  0
 23 24  1  0
 23 25  1  0
 23 26  1  0
M  END

Associated Targets(Human)

CCR1 Tchem C-C chemokine receptor type 1 (1730 Activities)

Discover Target: CCR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CCR2 Tchem C-C chemokine receptor type 2 (5628 Activities)

Discover Target: CCR2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Natural Product: No	Oral: No	Chemical Probe: No	Parenteral: No
Molecule Type: Unknown	Topical: No	First In Class: No	Black Box: No
Chirality: No	Availability: No	Prodrug: No

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 367.37	Molecular Weight (Monoisotopic): 367.1395	AlogP: 4.40	#Rotatable Bonds: 3
Polar Surface Area: 57.61	Molecular Species: NEUTRAL	HBA: 3	HBD: 1
#RO5 Violations: ┄	HBA (Lipinski): 4	HBD (Lipinski): 1	#RO5 Violations (Lipinski): ┄
CX Acidic pKa: 7.86	CX Basic pKa: ┄	CX LogP: 3.75	CX LogD: 3.62
Aromatic Rings: 1	Heavy Atoms: 26	QED Weighted: 0.86	Np Likeness Score: -0.92

References

1. Ortiz Zacarías NV, van Veldhoven JPD, Portner L, van Spronsen E, Ullo S, Veenhuizen M, van der Velden WJC, Zweemer AJM, Kreekel RM, Oenema K, Lenselink EB, Heitman LH, IJzerman AP.. (2018) Pyrrolone Derivatives as Intracellular Allosteric Modulators for Chemokine Receptors: Selective and Dual-Targeting Inhibitors of CC Chemokine Receptors 1 and 2., 61 (20): [PMID:30256641] [10.1021/acs.jmedchem.8b00605]
2. Ng, H P HP and 10 more authors. 1999-11-04 Discovery of novel non-peptide CCR1 receptor antagonists. [PMID:10579830]
3. Sabroe, I I and 7 more authors. 2000-08-25 A small molecule antagonist of chemokine receptors CCR1 and CCR3. Potent inhibition of eosinophil function and CCR3-mediated HIV-1 entry. [PMID:10854442]
4. Naya, A A and 7 more authors. 2001-04-26 Design, synthesis, and discovery of a novel CCR1 antagonist. [PMID:11311066]
5. Gladue, Ronald P RP and 19 more authors. 2003-10-17 CP-481,715, a potent and selective CCR1 antagonist with potential therapeutic implications for inflammatory diseases. [PMID:12909630]
6. Revesz, Laszlo L and 12 more authors. 2005-12-01 Novel CCR1 antagonists with oral activity in the mouse collagen induced arthritis. [PMID:16198561]
7. Xie, Yun Feng YF and 15 more authors. 2007-06-15 Structure-activity relationships of novel, highly potent, selective, and orally active CCR1 antagonists. [PMID:17446072]
8. Liu, Huaqing H and 18 more authors. 2008-11-27 cis-4-(Piperazin-1-yl)-5,6,7a,8,9,10,11,11a-octahydrobenzofuro[2,3-h]quinazolin-2-amine (A-987306), a new histamine H4R antagonist that blocks pain responses against carrageenan-induced hyperalgesia. [PMID:18983139]
9. Merritt, J Robert JR and 19 more authors. 2009-03-12 Novel pyrrolidine ureas as C-C chemokine receptor 1 (CCR1) antagonists. [PMID:19183043]
10. Furber, Mark M and 15 more authors. 2012-12-15 Discovery and evolution of phenoxypiperidine hydroxyamide dual CCR3/H₁ antagonists. Part I. [PMID:23142617]
11. Gardner, Daniel S DS and 23 more authors. 2013-07-01 The discovery of BMS-457, a potent and selective CCR1 antagonist. [PMID:23707259]
12. Santella, Joseph B JB and 26 more authors. 2014-09-25 Discovery of the CCR1 antagonist, BMS-817399, for the treatment of rheumatoid arthritis. [PMID:25101488]
13. Gege, Christian and 15 more authors. 2018-05-15 Identification and biological evaluation of thiazole-based inverse agonists of RORγt. [PMID:29631962]
14. Ortiz Zacarías, Natalia V and 12 more authors. 2018-10-25 Pyrrolone Derivatives as Intracellular Allosteric Modulators for Chemokine Receptors: Selective and Dual-Targeting Inhibitors of CC Chemokine Receptors 1 and 2. [PMID:30256641]
15. Harcken, Christian C and 21 more authors. 2019-02-01 Discovery and optimization of pyrazole amides as antagonists of CCR1. [PMID:30455146]
16. Harcken, Christian C and 21 more authors. 2019-02-01 Identification of novel azaindazole CCR1 antagonist clinical candidates. [PMID:30595446]

4-Acetyl-5-cyclohexyl-3-hydroxy-1-(3-(trifluoromethyl)phenyl)-1,5-dihydro-2H-pyrrol-2-one

Names and Identifiers

Alternative Forms

Associated Targets(Human)

Molecule Features

Drug Indications

Mechanisms of Action

Biocomponents

Calculated Properties

References

Source