(E)-3-oxo-1,3-dihydroisobenzofuran-5-yl-(4-nitro)cinnamate

ID: ALA4557755

PubChem CID: 155554831

Max Phase: Preclinical

Molecular Formula: C17H11NO6

Molecular Weight: 325.28

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=C(/C=C/c1ccc([N+](=O)[O-])cc1)Oc1ccc2c(c1)C(=O)OC2

Standard InChI:  InChI=1S/C17H11NO6/c19-16(8-3-11-1-5-13(6-2-11)18(21)22)24-14-7-4-12-10-23-17(20)15(12)9-14/h1-9H,10H2/b8-3+

Standard InChI Key:  IJXFGVHHWBRVQT-FPYGCLRLSA-N

Molfile:  

 
     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
   34.1679   -3.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1668   -4.1006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8748   -4.5096    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8730   -2.8722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5816   -3.2775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5819   -4.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3606   -4.3489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.8416   -3.6864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.3601   -3.0244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.6124   -2.2471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   33.4601   -2.8727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.7525   -3.2814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0447   -2.8730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7527   -4.0986    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.3371   -3.2818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6293   -2.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6329   -2.0559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9260   -1.6476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2174   -2.0564    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.2202   -2.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.9277   -3.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.5080   -1.6520    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.8009   -2.0617    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.5067   -0.8349    0.0000 O   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  1  0
  9  5  1  0
  9 10  2  0
  1 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
 22 23  2  0
 22 24  1  0
 19 22  1  0
M  CHG  2  22   1  24  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4557755

   ---

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: 325.28

Molecular Weight (Monoisotopic): 325.0586

AlogP: 2.88

#Rotatable Bonds: 4

Polar Surface Area: 95.74

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.70

CX Basic pKa: ┄

CX LogP: 3.67

CX LogD: 3.67

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.28

Np Likeness Score: -0.08

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