Ethyl (E)-6-chloro-3-((2-(2-phenylacetyl)hydrazineylidene)methyl)-1H-indole-2-carboxylate

ID: ALA4560037

PubChem CID: 155510499

Max Phase: Preclinical

Molecular Formula: C20H18ClN3O3

Molecular Weight: 383.84

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1[nH]c2cc(Cl)ccc2c1/C=N/NC(=O)Cc1ccccc1

Standard InChI:  InChI=1S/C20H18ClN3O3/c1-2-27-20(26)19-16(15-9-8-14(21)11-17(15)23-19)12-22-24-18(25)10-13-6-4-3-5-7-13/h3-9,11-12,23H,2,10H2,1H3,(H,24,25)/b22-12+

Standard InChI Key:  PENJNCRLDPUWHT-WSDLNYQXSA-N

Molfile:  

 
     RDKit          2D

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   38.7821   -4.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.7810   -5.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4890   -5.6075    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.4873   -3.9701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1959   -4.3754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.1961   -5.1985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9791   -5.4527    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.4628   -4.7866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.9787   -4.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.0730   -5.6065    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   42.2800   -4.7863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.6889   -5.4938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.6884   -4.0784    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.5060   -5.4936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.9149   -6.2011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.2310   -3.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0303   -3.1734    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.2825   -2.3961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.0818   -2.2259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.3341   -1.4487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   43.6288   -2.8330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.4281   -2.6629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.9713   -3.2738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.7699   -3.1041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   46.0229   -2.3261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   45.4711   -1.7176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.6745   -1.8904    0.0000 C   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
 11 13  2  0
 12 14  1  0
 14 15  1  0
  9 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  1  0
 19 20  2  0
 19 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4560037

   ---

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: 383.84

Molecular Weight (Monoisotopic): 383.1037

AlogP: 3.69

#Rotatable Bonds: 6

Polar Surface Area: 83.55

Molecular Species: NEUTRAL

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.97

CX Basic pKa: 0.76

CX LogP: 3.93

CX LogD: 3.93

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.39

Np Likeness Score: -1.40

References

1. van der Vlag R, Guo H, Hapko U, Eleftheriadis N, Monjas L, Dekker FJ, Hirsch AKH..  (2019)  A combinatorial approach for the discovery of drug-like inhibitors of 15-lipoxygenase-1.,  174  [PMID:31026746] [10.1016/j.ejmech.2019.04.021]

Source

Source(1):

• Scientific Literature