6-Chloro-3-[(1,1-dioxo-tetrahydro-1lambda(6)-thiophene-3-carbonyl)-hydrazonomethyl]-1H-indole-2-carboxylic acid ethyl ester

ID: ALA4474190

PubChem CID: 155536907

Max Phase: Preclinical

Molecular Formula: C17H18ClN3O5S

Molecular Weight: 411.87

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CCOC(=O)c1[nH]c2cc(Cl)ccc2c1/C=N/NC(=O)C1CCS(=O)(=O)C1

Standard InChI:  InChI=1S/C17H18ClN3O5S/c1-2-26-17(23)15-13(12-4-3-11(18)7-14(12)20-15)8-19-21-16(22)10-5-6-27(24,25)9-10/h3-4,7-8,10,20H,2,5-6,9H2,1H3,(H,21,22)/b19-8+

Standard InChI Key:  NZCWHBVDVMMODU-UFWORHAWSA-N

Molfile:  

 
     RDKit          2D

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   20.4199  -16.7993    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.6241  -17.0159    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   20.2097  -17.5968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5855  -17.9408    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5843  -18.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2991  -19.1810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2973  -17.5280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0126  -17.9372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0175  -18.7636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8049  -19.0144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2868  -18.3429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7971  -17.6773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8695  -19.1801    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   16.0474  -16.8912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8534  -16.7150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1036  -15.9289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.9095  -15.7526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1599  -14.9666    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.1118  -18.3380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5284  -19.0501    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.5200  -17.6212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3534  -19.0452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7701  -19.7572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4651  -16.3624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2999  -17.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0167  -17.5751    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2866  -16.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
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  5 13  1  0
 12 14  1  0
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 17 18  2  0
 11 19  1  0
 19 20  1  0
 19 21  2  0
 20 22  1  0
 22 23  1  0
 17 24  1  0
 24 25  1  0
 25 26  1  0
 26  2  1  0
  2 27  1  0
 27 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4474190

   ---

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: 411.87

Molecular Weight (Monoisotopic): 411.0656

AlogP: 1.88

#Rotatable Bonds: 5

Polar Surface Area: 117.69

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: 0.39

CX LogP: 1.10

CX LogD: 1.10

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.44

Np Likeness Score: -1.84

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