1-((6-Chloropyridin-3-yl)methyl)-5-methyl-7-nitro-2,3,5,6-tetrahydro-1Hpyrrolo[1,2-a]imidazole-5,6-diol

ID: ALA2288927

PubChem CID: 71517942

Max Phase: Preclinical

Molecular Formula: C13H15ClN4O4

Molecular Weight: 326.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(O)C(O)C([N+](=O)[O-])=C2N(Cc3ccc(Cl)nc3)CCN21

Standard InChI:  InChI=1S/C13H15ClN4O4/c1-13(20)11(19)10(18(21)22)12-16(4-5-17(12)13)7-8-2-3-9(14)15-6-8/h2-3,6,11,19-20H,4-5,7H2,1H3

Standard InChI Key:  LGWYUUYJKRTMFC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    0.8540   -4.8502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8528   -5.6788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5694   -6.0945    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2875   -5.6784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2847   -4.8465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5676   -4.4388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1363   -6.0935    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.9952   -4.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7864   -4.6717    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0583   -5.4525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8846   -5.4370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4455   -4.1715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1201   -4.6443    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7772   -4.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5061   -3.3698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6841   -3.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1860   -2.7332    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3659   -2.8340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5066   -1.9718    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9813   -2.6918    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1831   -4.8585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4905   -3.7290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  2  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 13  1  0
 12  9  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  2  0
 17 18  2  0
 17 19  1  0
 16 17  1  0
 15 20  1  0
 14 21  1  0
 14 22  1  0
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA2288927

   1-[(6-chloropyridin-3-yl)methyl]-5-methyl-7-nitro-3,6-dihydro-2H-pyrrolo[1,2-a]imidazole-5,6-diol

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: 326.74

Molecular Weight (Monoisotopic): 326.0782

AlogP: 0.38

#Rotatable Bonds: 3

Polar Surface Area: 102.97

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.64

CX Basic pKa: 0.62

CX LogP: 0.54

CX LogD: 0.54

Aromatic Rings: 1

Heavy Atoms: 22

QED Weighted: 0.47

Np Likeness Score: -0.66

References

1. Ye Z, Shi L, Shao X, Xu X, Xu Z, Li Z..  (2013)  Pyrrole- and dihydropyrrole-fused neonicotinoids: design, synthesis, and insecticidal evaluation.,  61  (2): [PMID:23256728] [10.1021/jf3044132]

Source

Source(1):

• Scientific Literature