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

ID: ALA4547876

PubChem CID: 155554130

Max Phase: Preclinical

Molecular Formula: C22H21ClN2O4

Molecular Weight: 412.87

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1[nH]c2cc(Cl)ccc2c1/C=C/C(=O)NCc1cccc(OC)c1

Standard InChI:  InChI=1S/C22H21ClN2O4/c1-3-29-22(27)21-18(17-8-7-15(23)12-19(17)25-21)9-10-20(26)24-13-14-5-4-6-16(11-14)28-2/h4-12,25H,3,13H2,1-2H3,(H,24,26)/b10-9+

Standard InChI Key:  VMVSYADKAQVSPU-MDZDMXLPSA-N

Molfile:  

 
     RDKit          2D

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   15.3365  -17.3164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3347  -15.6790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0433  -16.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0436  -16.9075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8266  -17.1617    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3103  -16.4955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8262  -15.8298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9204  -17.3155    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   18.1275  -16.4952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5363  -17.2028    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3535  -17.2025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7623  -17.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5358  -15.7874    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.0784  -15.0525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8777  -14.8823    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1300  -14.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9293  -13.9349    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.5830  -13.4979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1815  -13.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.9808  -12.9874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5237  -13.5954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3223  -13.4258    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5753  -12.6478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0235  -12.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.2269  -12.2121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8690  -14.0332    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.6684  -13.8634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 24 28  1  0
 28 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4547876

   ---

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: 412.87

Molecular Weight (Monoisotopic): 412.1190

AlogP: 4.34

#Rotatable Bonds: 7

Polar Surface Area: 80.42

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.02

CX Basic pKa: ┄

CX LogP: 4.10

CX LogD: 4.10

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.45

Np Likeness Score: -0.99

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