N,N,N',N'-Tetramethyl-6-[N'-(5-nitro-furan-2-ylmethylene)-hydrazino]-[1,3,5]triazine-2,4-diamine

ID: ALA364229

PubChem CID: 9996112

Max Phase: Preclinical

Molecular Formula: C12H16N8O3

Molecular Weight: 320.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(C)c1nc(N/N=C/c2ccc([N+](=O)[O-])o2)nc(N(C)C)n1

Standard InChI:  InChI=1S/C12H16N8O3/c1-18(2)11-14-10(15-12(16-11)19(3)4)17-13-7-8-5-6-9(23-8)20(21)22/h5-7H,1-4H3,(H,14,15,16,17)/b13-7+

Standard InChI Key:  PBEBFUUXRFKKES-NTUHNPAUSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
   -3.9333    1.8500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9333    1.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2208    2.2708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000    1.8500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2208    0.6083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.7667    0.7708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5417    0.4750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5000    1.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0792    0.3208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5500    1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4375    0.8333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708    1.0250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2208    3.0875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6458    0.6083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7292    1.6083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6750   -0.3417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750    1.1583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583    0.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833    0.6083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5083    3.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6458   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9333    3.4958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3583    1.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  3  2  0
  5  2  1  0
  6  9  1  0
  7  6  1  0
  8  4  1  0
  9 11  1  0
 10 15  1  0
 11 18  1  0
 12 19  1  0
 13  3  1  0
 14  2  1  0
 15 11  2  0
 16  7  1  0
 17  7  2  0
 18 12  2  0
 19  8  1  0
 20 13  1  0
 21 14  1  0
 22 13  1  0
 23 14  1  0
  8  5  2  0
 10  6  2  0
M  CHG  2   7   1  16  -1
M  END

Alternative Forms

1. Parent:

   

   ALA364229

   2-N,2-N,4-N,4-N-tetramethyl-6-N-[(E)-(5-nitrofuran-2-yl)methylideneamino]-1,3,5-triazine-2,4,6-triamine

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: 320.31

Molecular Weight (Monoisotopic): 320.1345

AlogP: 0.95

#Rotatable Bonds: 6

Polar Surface Area: 125.82

Molecular Species: ZWITTERION

HBA: 10

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 5.56

CX Basic pKa: 9.15

CX LogP: 3.03

CX LogD: 2.13

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.47

Np Likeness Score: -1.79

References

1. Baliani A, Bueno GJ, Stewart ML, Yardley V, Brun R, Barrett MP, Gilbert IH..  (2005)  Design and synthesis of a series of melamine-based nitroheterocycles with activity against Trypanosomatid parasites.,  48  (17): [PMID:16107157] [10.1021/jm050177+]

Source

Source(1):

• Scientific Literature