Ethyl (E)-6-Chloro-3-(3-((2-chlorophenethyl)amino)-3-oxoprop-1-en-1-yl)-1H-indole-2-carboxylate

ID: ALA4558072

PubChem CID: 155554639

Max Phase: Preclinical

Molecular Formula: C22H20Cl2N2O3

Molecular Weight: 431.32

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1[nH]c2cc(Cl)ccc2c1/C=C/C(=O)NCCc1ccccc1Cl

Standard InChI:  InChI=1S/C22H20Cl2N2O3/c1-2-29-22(28)21-17(16-8-7-15(23)13-19(16)26-21)9-10-20(27)25-12-11-14-5-3-4-6-18(14)24/h3-10,13,26H,2,11-12H2,1H3,(H,25,27)/b10-9+

Standard InChI Key:  STLJWSQEJDGIFJ-MDZDMXLPSA-N

Molfile:  

 
     RDKit          2D

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   14.1426  -27.6359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1415  -28.4554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8495  -28.8644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8477  -27.2270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5563  -27.6323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5566  -28.4555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3396  -28.7096    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.8233  -28.0435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3391  -27.3777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4334  -28.8635    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   17.6405  -28.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0493  -28.7508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8665  -28.7505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2753  -29.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0488  -27.3354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5914  -26.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3907  -26.4303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6430  -25.6530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4423  -25.4829    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.0960  -25.0459    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.6945  -24.7056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4938  -24.5354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7461  -23.7581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5455  -23.5922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7979  -22.8158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2506  -22.2077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4477  -22.3813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1991  -23.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4006  -23.3314    0.0000 Cl  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
  2 10  1  0
  8 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 11 15  2  0
  9 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4558072

   ---

Molecule Features

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: 431.32

Molecular Weight (Monoisotopic): 430.0851

AlogP: 5.02

#Rotatable Bonds: 7

Polar Surface Area: 71.19

Molecular Species: NEUTRAL

HBA: 3

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 11.02

CX Basic pKa: ┄

CX LogP: 5.15

CX LogD: 5.15

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.41

Np Likeness Score: -1.02

References

1. Guo H, Verhoek IC, Prins GGH, van der Vlag R, van der Wouden PE, van Merkerk R, Quax WJ, Olinga P, Hirsch AKH, Dekker FJ..  (2019)  Novel 15-Lipoxygenase-1 Inhibitor Protects Macrophages from Lipopolysaccharide-Induced Cytotoxicity.,  62  (9): [PMID:30964295] [10.1021/acs.jmedchem.9b00212]

Source

Source(1):

• Scientific Literature