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

ID: ALA4066587

PubChem CID: 2247579

Max Phase: Preclinical

Molecular Formula: C10H15N3O4

Molecular Weight: 241.25

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C10H15N3O4/c1-12(2)7-3-6-11-10(14)8-4-5-9(17-8)13(15)16/h4-5H,3,6-7H2,1-2H3,(H,11,14)

Standard InChI Key:  VDCUKJRGHJAYON-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
   21.7463   -4.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5635   -4.0365    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.8179   -3.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1549   -2.7776    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4962   -3.2598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5954   -3.0083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.2020   -3.5560    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.7665   -2.2092    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7165   -3.0053    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1095   -3.5524    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.5463   -2.2061    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.9795   -3.3045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.5860   -3.8522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3636   -3.6007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.9701   -4.1484    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.7477   -3.8969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7991   -4.9475    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
M  CHG  2   9   1  11  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4066587

   N-[3-(Dimethylamino)propyl]-5-nitro-2-furamide

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: 241.25

Molecular Weight (Monoisotopic): 241.1063

AlogP: 0.87

#Rotatable Bonds: 6

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: 11.26

CX Basic pKa: 9.29

CX LogP: 0.12

CX LogD: -1.68

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.45

Np Likeness Score: -1.98

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