Ethyl (E)-6-chloro-3-((2-(2-(thiophen-2-yl)acetyl)hydrazineylidene)methyl)-1H-indole-2-carboxylate

ID: ALA4558426

PubChem CID: 155557748

Max Phase: Preclinical

Molecular Formula: C18H16ClN3O3S

Molecular Weight: 389.86

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1[nH]c2cc(Cl)ccc2c1/C=N/NC(=O)Cc1cccs1

Standard InChI:  InChI=1S/C18H16ClN3O3S/c1-2-25-18(24)17-14(13-6-5-11(19)8-15(13)21-17)10-20-22-16(23)9-12-4-3-7-26-12/h3-8,10,21H,2,9H2,1H3,(H,22,23)/b20-10+

Standard InChI Key:  YJTITVPJWIWOPY-KEBDBYFISA-N

Molfile:  

 
     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    2.7762  -14.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7751  -14.9841    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4831  -15.3931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4813  -13.7557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1899  -14.1610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1902  -14.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9732  -15.2384    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4569  -14.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9728  -13.9065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0670  -15.3922    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.2741  -14.5719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6829  -15.2795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6824  -13.8641    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5001  -15.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9089  -15.9868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2250  -13.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0243  -12.9590    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2766  -12.1818    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.0759  -12.0116    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3281  -11.2343    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6229  -12.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4221  -12.4485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0281  -12.9925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7356  -12.5837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5655  -11.7844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7527  -11.6993    0.0000 S   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 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4558426

   ---

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: 389.86

Molecular Weight (Monoisotopic): 389.0601

AlogP: 3.75

#Rotatable Bonds: 6

Polar Surface Area: 83.55

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.97

CX Basic pKa: 0.59

CX LogP: 3.84

CX LogD: 3.84

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.38

Np Likeness Score: -2.02

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