5-(5-Chloro-1-methyl-2-(6,6,6-trifluorohexyl)-1Hindol-3-yl)-3-methyl-5-oxopentanoic Acid

ID: ALA4278772

PubChem CID: 145982307

Max Phase: Preclinical

Molecular Formula: C21H25ClF3NO3

Molecular Weight: 431.88

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(CC(=O)O)CC(=O)c1c(CCCCCC(F)(F)F)n(C)c2ccc(Cl)cc12

Standard InChI:  InChI=1S/C21H25ClF3NO3/c1-13(11-19(28)29)10-18(27)20-15-12-14(22)7-8-16(15)26(2)17(20)6-4-3-5-9-21(23,24)25/h7-8,12-13H,3-6,9-11H2,1-2H3,(H,28,29)

Standard InChI Key:  QJQXCFTWJLJMSB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
    8.7109  -10.8706    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7097  -11.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4245  -12.1108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4227  -10.4578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1380  -10.8669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1429  -11.6933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9304  -11.9442    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4123  -11.2726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9225  -10.6070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9963  -10.4583    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   11.1899  -12.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1729   -9.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9788   -9.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6173   -9.2111    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2292   -8.8586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0351   -8.6823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6735   -8.2488    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2855   -7.8963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0914   -7.7200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.7298   -7.2864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2081  -11.0539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9212  -11.4687    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9186  -12.2937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6317  -12.7084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6291  -13.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3422  -13.9482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3396  -14.7731    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.0580  -13.5379    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   15.0539  -14.3580    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  6  2  0
  5  4  2  0
  4  1  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9  5  1  0
  1 10  1  0
  7 11  1  0
  9 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 16 18  1  0
 18 19  1  0
 18 20  2  0
  8 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4278772

   ---

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: 431.88

Molecular Weight (Monoisotopic): 431.1475

AlogP: 6.18

#Rotatable Bonds: 10

Polar Surface Area: 59.30

Molecular Species: ACID

HBA: 3

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 4.35

CX Basic pKa: ┄

CX LogP: 5.70

CX LogD: 2.78

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.36

Np Likeness Score: -0.27

References

1. Chourey S, Ye Q, Reddy CN, Wang R, Cossette C, Gravel S, Slobodchikova I, Vuckovic D, Rokach J, Powell WS..  (2018)  Novel Highly Potent and Metabolically Resistant Oxoeicosanoid (OXE) Receptor Antagonists That Block the Actions of the Granulocyte Chemoattractant 5-Oxo-6,8,11,14-Eicosatetraenoic Acid (5-oxo-ETE).,  61  (14): [PMID:29972644] [10.1021/acs.jmedchem.8b00154]

Source

Source(1):

• Scientific Literature