2-(1-(2-(5-chloro-2-hexyl-1-methyl-1H-indol-3-yl)-2-oxoethyl)cyclopropyl)acetic acid

ID: ALA4081391

PubChem CID: 137645745

Max Phase: Preclinical

Molecular Formula: C22H28ClNO3

Molecular Weight: 389.92

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCc1c(C(=O)CC2(CC(=O)O)CC2)c2cc(Cl)ccc2n1C

Standard InChI:  InChI=1S/C22H28ClNO3/c1-3-4-5-6-7-18-21(16-12-15(23)8-9-17(16)24(18)2)19(25)13-22(10-11-22)14-20(26)27/h8-9,12H,3-7,10-11,13-14H2,1-2H3,(H,26,27)

Standard InChI Key:  MNJIVPMZNMUMAC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   18.2424  -16.1540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0348  -16.3686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.8244  -15.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6811  -19.3991    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1758  -18.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7072  -18.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9090  -19.1316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9269  -18.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2314  -17.8957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5174  -18.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5034  -19.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1996  -19.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8176  -17.8663    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.9176  -20.1814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9731  -17.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7752  -17.1471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4368  -16.6865    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8433  -16.2183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1091  -15.4455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9113  -15.2894    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.5729  -14.8289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9928  -18.7655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4160  -18.0664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2330  -18.0834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6562  -17.3843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4732  -17.4013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8964  -16.7022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  1  3  1  0
  7  4  1  0
  4  5  1  0
  5  6  2  0
  6  8  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12  7  1  0
 10 13  1  0
  4 14  1  0
  6 15  1  0
 15 16  1  0
 15 17  2  0
 16  2  1  0
  2 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
  5 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4081391

   ---

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: 389.92

Molecular Weight (Monoisotopic): 389.1758

AlogP: 5.78

#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: 4.32

CX Basic pKa: ┄

CX LogP: 5.35

CX LogD: 2.40

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.41

Np Likeness Score: -0.19

References

1. Ye Q, Chourey S, Wang R, Chintam NR, Gravel S, Powell WS, Rokach J..  (2017)  Structure-activity relationship study of β-oxidation resistant indole-based 5-oxo-6,8,11,14-eicosatetraenoic acid (5-oxo-ETE) receptor antagonists.,  27  (20): [PMID:28943042] [10.1016/j.bmcl.2017.08.034]

Source

Source(1):

• Scientific Literature