(E)-ethyl 6-chloro-3-((2-(3-(dimethylamino)propanoyl)hydrazono)methyl)-1H-indole-2-carboxylate

ID: ALA4474467

PubChem CID: 155537062

Max Phase: Preclinical

Molecular Formula: C17H21ClN4O3

Molecular Weight: 364.83

Molecule Type: Unknown

Names and Identifiers

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

Standard InChI:  InChI=1S/C17H21ClN4O3/c1-4-25-17(24)16-13(10-19-21-15(23)7-8-22(2)3)12-6-5-11(18)9-14(12)20-16/h5-6,9-10,20H,4,7-8H2,1-3H3,(H,21,23)/b19-10+

Standard InChI Key:  GMEAECFBAROULJ-VXLYETTFSA-N

Molfile:  

 
     RDKit          2D

 25 26  0  0  0  0  0  0  0  0999 V2000
    4.2817  -19.1906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2805  -20.0179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9953  -20.4307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9935  -18.7778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7088  -19.1869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7137  -20.0133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5011  -20.2641    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9830  -19.5927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4933  -18.9270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5658  -20.4297    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.7436  -18.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5495  -17.9647    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.7998  -17.1786    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6057  -17.0024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8560  -16.2164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8080  -19.5878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2246  -20.2998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2162  -18.8710    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0495  -20.2950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4663  -21.0070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1613  -17.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9672  -17.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5228  -18.0458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.3288  -17.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2725  -18.8319    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
  9 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
  8 16  1  0
 16 17  1  0
 16 18  2  0
 17 19  1  0
 19 20  1  0
 14 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474467

   ---

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: 364.83

Molecular Weight (Monoisotopic): 364.1302

AlogP: 2.40

#Rotatable Bonds: 7

Polar Surface Area: 86.79

Molecular Species: BASE

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.03

CX Basic pKa: 9.08

CX LogP: 1.90

CX LogD: 0.48

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.45

Np Likeness Score: -1.58

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