5-Nitro-furan-2-carboxylic acid (3-diethylamino-propyl)-amide

ID: ALA4088638

PubChem CID: 3312702

Max Phase: Preclinical

Molecular Formula: C12H19N3O4

Molecular Weight: 269.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCN(CC)CCCNC(=O)c1ccc([N+](=O)[O-])o1

Standard InChI:  InChI=1S/C12H19N3O4/c1-3-14(4-2)9-5-8-13-12(16)10-6-7-11(19-10)15(17)18/h6-7H,3-5,8-9H2,1-2H3,(H,13,16)

Standard InChI Key:  DKWGBKJZAAPJOE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 19  0  0  0  0  0  0  0  0999 V2000
   21.9981   -8.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8153   -8.8034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0697   -8.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.4067   -7.5446    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.7480   -8.0267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.8472   -7.7753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4537   -8.3229    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.0182   -6.9762    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.9683   -7.7723    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.3612   -8.3194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7980   -6.9730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.2313   -8.0715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8378   -8.6191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.6154   -8.3677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2219   -8.9153    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.9994   -8.6639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.0509   -9.7144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6574  -10.2621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.6060   -9.2115    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
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 16 19  1  0
M  CHG  2   9   1  11  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4088638

   N-[3-(diethylamino)propyl]-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: 269.30

Molecular Weight (Monoisotopic): 269.1376

AlogP: 1.65

#Rotatable Bonds: 8

Polar Surface Area: 88.62

Molecular Species: BASE

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.27

CX Basic pKa: 9.82

CX LogP: 0.74

CX LogD: -1.47

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.44

Np Likeness Score: -2.06

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