5-Nitro-furan-2-carboxylic acid sec-butylamide

ID: ALA4103302

PubChem CID: 4273319

Max Phase: Preclinical

Molecular Formula: C9H12N2O4

Molecular Weight: 212.21

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C9H12N2O4/c1-3-6(2)10-9(12)7-4-5-8(15-7)11(13)14/h4-6H,3H2,1-2H3,(H,10,12)

Standard InChI Key:  QRBOMDOFHIYOCJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 15 15  0  0  0  0  0  0  0  0999 V2000
   14.6558   -9.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4729   -9.7485    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7273   -8.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0644   -8.4897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4056   -8.9718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5049   -8.7204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1114   -9.2680    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6759   -7.9213    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.6260   -8.7174    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0189   -9.2645    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4557   -7.9182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.8889   -9.0166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4955   -9.5642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2730   -9.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0600   -8.2175    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
 12 15  1  0
M  CHG  2   9   1  11  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4103302

   N-(Sec-butyl)-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: 212.21

Molecular Weight (Monoisotopic): 212.0797

AlogP: 1.72

#Rotatable Bonds: 4

Polar Surface Area: 85.38

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.39

CX Basic pKa: ┄

CX LogP: 1.43

CX LogD: 1.43

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.61

Np Likeness Score: -2.15

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