Ethyl (E)-6-chloro-3-((2-(2-(3,4-dimethoxyphenyl)acetyl)hydrazineylidene)methyl)-1H-indole-2-carboxylate

ID: ALA4546737

PubChem CID: 155552537

Max Phase: Preclinical

Molecular Formula: C22H22ClN3O5

Molecular Weight: 443.89

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1[nH]c2cc(Cl)ccc2c1/C=N/NC(=O)Cc1ccc(OC)c(OC)c1

Standard InChI:  InChI=1S/C22H22ClN3O5/c1-4-31-22(28)21-16(15-7-6-14(23)11-17(15)25-21)12-24-26-20(27)10-13-5-8-18(29-2)19(9-13)30-3/h5-9,11-12,25H,4,10H2,1-3H3,(H,26,27)/b24-12+

Standard InChI Key:  IIBPHBFOHAZVNF-WYMPLXKRSA-N

Molfile:  

 
     RDKit          2D

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   26.6841  -25.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   28.0990  -24.7474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0992  -25.5705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8822  -25.8247    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.3659  -25.1586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8818  -24.4928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9761  -25.9785    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   30.1831  -25.1583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5919  -25.8658    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.5915  -24.4504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.4091  -25.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8180  -26.5731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1341  -23.7155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9333  -23.5454    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.1856  -22.7681    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.9849  -22.5979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.2372  -21.8207    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.5319  -23.2050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.3312  -23.0349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8744  -23.6458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6730  -23.4761    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9259  -22.6981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3742  -22.0896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.5776  -22.2624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6237  -21.3115    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.4224  -21.1385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.7250  -22.5269    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.2728  -23.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
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  9 16  1  0
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 26 27  2  0
 27 22  1  0
 26 28  1  0
 28 29  1  0
 25 30  1  0
 30 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4546737

   ---

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: 443.89

Molecular Weight (Monoisotopic): 443.1248

AlogP: 3.71

#Rotatable Bonds: 8

Polar Surface Area: 102.01

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.97

CX Basic pKa: 0.58

CX LogP: 3.61

CX LogD: 3.61

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.31

Np Likeness Score: -1.15

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