5-Nitro-furan-2-carboxylic acid dibenzylamide

ID: ALA4091464

PubChem CID: 3269063

Max Phase: Preclinical

Molecular Formula: C19H16N2O4

Molecular Weight: 336.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(c1ccc([N+](=O)[O-])o1)N(Cc1ccccc1)Cc1ccccc1

Standard InChI:  InChI=1S/C19H16N2O4/c22-19(17-11-12-18(25-17)21(23)24)20(13-15-7-3-1-4-8-15)14-16-9-5-2-6-10-16/h1-12H,13-14H2

Standard InChI Key:  LSBAOURNDLAOQW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
   30.0173   -3.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8345   -3.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.0889   -3.2102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.4259   -2.7281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.7672   -3.2102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.8664   -2.9588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4729   -3.5064    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   32.0374   -2.1597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.9875   -2.9558    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.3805   -3.5029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.8172   -2.1565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   32.3019   -4.3055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.2505   -3.2550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9085   -4.8532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.4215   -2.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7333   -5.6487    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.3390   -6.1961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.1175   -5.9448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2869   -5.1410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.6798   -4.5971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.2005   -2.2060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.3717   -1.4077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.7648   -0.8592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9840   -1.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.8165   -1.9121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
  3  6  1  0
  6  7  1  0
  6  8  2  0
  9 10  2  0
  9 11  1  0
  5  9  1  0
  7 12  1  0
  7 13  1  0
 12 14  1  0
 13 15  1  0
 14 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 14  1  0
 15 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 15  1  0
M  CHG  2   9   1  11  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4091464

   N,N-dibenzyl-5-nitrofuran-2-carboxamide

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 336.35

Molecular Weight (Monoisotopic): 336.1110

AlogP: 4.03

#Rotatable Bonds: 6

Polar Surface Area: 76.59

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.81

CX LogD: 3.81

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.50

Np Likeness Score: -1.38

References

1. Arias DG, Herrera FE, Garay AS, Rodrigues D, Forastieri PS, Luna LE, Bürgi MD, Prieto C, Iglesias AA, Cravero RM, Guerrero SA..  (2017)  Rational design of nitrofuran derivatives: Synthesis and valuation as inhibitors of Trypanosoma cruzi trypanothione reductase.,  125  [PMID:27810595] [10.1016/j.ejmech.2016.10.055]

Source

Source(1):

• Scientific Literature