3-(1-(4-chlorobenzyl)-1H-1,2,3-triazol-4-yl)propyl cinnamate

ID: ALA4540733

PubChem CID: 155549903

Max Phase: Preclinical

Molecular Formula: C21H20ClN3O2

Molecular Weight: 381.86

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccccc1)OCCCc1cn(Cc2ccc(Cl)cc2)nn1

Standard InChI:  InChI=1S/C21H20ClN3O2/c22-19-11-8-18(9-12-19)15-25-16-20(23-24-25)7-4-14-27-21(26)13-10-17-5-2-1-3-6-17/h1-3,5-6,8-13,16H,4,7,14-15H2/b13-10+

Standard InChI Key:  FWDCXKYNERSZGY-JLHYYAGUSA-N

Molfile:  

 
     RDKit          2D

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   28.2401   -2.6768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9481   -3.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6578   -2.6763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.6549   -1.8536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9463   -1.4484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3611   -1.4424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0703   -1.8483    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7765   -1.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4858   -1.8429    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.1919   -1.4317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.9012   -1.8376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.7734   -0.6198    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.6073   -1.4264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.3166   -1.8323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.4089   -2.6398    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.2088   -2.8067    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.6148   -2.0974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.0656   -1.4923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   36.5440   -3.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.3570   -3.6343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.6878   -4.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5001   -4.4628    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.9788   -3.7994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.6395   -3.0514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.8282   -2.9723    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.7919   -3.8807    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
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  6  1  1  0
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  7  8  2  0
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  9 10  1  0
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  9 13  2  0
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 18 19  2  0
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 21 22  2  0
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 26 21  1  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4540733

   ---

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: 381.86

Molecular Weight (Monoisotopic): 381.1244

AlogP: 4.17

#Rotatable Bonds: 8

Polar Surface Area: 57.01

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.32

CX LogP: 5.22

CX LogD: 5.22

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.33

Np Likeness Score: -1.07

References

1. Rodrigues MP, Tomaz DC, Ângelo de Souza L, Onofre TS, Aquiles de Menezes W, Almeida-Silva J, Suarez-Fontes AM, Rogéria de Almeida M, Manoel da Silva A, Bressan GC, Vannier-Santos MA, Rangel Fietto JL, Teixeira RR..  (2019)  Synthesis of cinnamic acid derivatives and leishmanicidal activity against Leishmania braziliensis.,  183  [PMID:31542714] [10.1016/j.ejmech.2019.111688]

Source

Source(1):

• Scientific Literature