5-Nitro-furan-2-carboxylic acid (2-dimethylamino-ethyl)-amide

ID: ALA4084206

PubChem CID: 17368088

Max Phase: Preclinical

Molecular Formula: C9H13N3O4

Molecular Weight: 227.22

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C9H13N3O4/c1-11(2)6-5-10-9(13)7-3-4-8(16-7)12(14)15/h3-4H,5-6H2,1-2H3,(H,10,13)

Standard InChI Key:  GPPNYRTXACDFDQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 16  0  0  0  0  0  0  0  0999 V2000
   14.7300  -23.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5472  -23.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8016  -22.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1386  -22.2045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.4799  -22.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5792  -22.4352    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1857  -22.9828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.7502  -21.6361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.7002  -22.4322    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0932  -22.9793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5300  -21.6329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.9632  -22.7314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5698  -23.2790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3473  -23.0276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.9538  -23.5752    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5183  -22.2285    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
 14 16  1  0
M  CHG  2   9   1  11  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4084206

   N-[2-(dimethylamino)ethyl]-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: 227.22

Molecular Weight (Monoisotopic): 227.0906

AlogP: 0.48

#Rotatable Bonds: 5

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: 11.24

CX Basic pKa: 8.51

CX LogP: 0.16

CX LogD: -0.98

Aromatic Rings: 1

Heavy Atoms: 16

QED Weighted: 0.58

Np Likeness Score: -2.18

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