6-Aziridin-1-yl-7-methoxy-2,3-dihydro-1H-benzo[d]pyrrolo[1,2-a]imidazole-5,8-dione

ID: ALA137523

PubChem CID: 383842

Max Phase: Preclinical

Molecular Formula: C13H13N3O3

Molecular Weight: 259.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1=C(N2CC2)C(=O)c2nc3n(c2C1=O)CCC3

Standard InChI:  InChI=1S/C13H13N3O3/c1-19-13-10(15-5-6-15)11(17)8-9(12(13)18)16-4-2-3-7(16)14-8/h2-6H2,1H3

Standard InChI Key:  GWZWHLZMISGGFG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 22  0  0  0  0  0  0  0  0999 V2000
    1.5042   -2.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5042   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4667   -2.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792   -3.2750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4667   -2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667   -2.1792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792   -3.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0583   -2.0750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4292   -2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3500   -1.5500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6500   -2.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9875   -3.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9792   -1.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0583   -3.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4292   -3.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042   -2.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0042   -3.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5750   -2.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  6  1  0
  4  2  1  0
  5  3  2  0
  6  1  1  0
  7  1  1  0
  8  2  1  0
  9  3  1  0
 10  7  2  0
 11  9  1  0
 12  9  1  0
 13  4  2  0
 14  6  2  0
 15  5  1  0
 16  8  1  0
 17 10  1  0
 18 17  1  0
 19 15  1  0
 10  8  1  0
  4  5  1  0
 16 18  1  0
 11 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA137523

   6-(aziridin-1-yl)-7-methoxy-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazole-5,8-dione

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: 259.26

Molecular Weight (Monoisotopic): 259.0957

AlogP: 0.38

#Rotatable Bonds: 2

Polar Surface Area: 64.20

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.03

CX LogP: -0.66

CX LogD: -0.66

Aromatic Rings: 1

Heavy Atoms: 19

QED Weighted: 0.72

Np Likeness Score: -0.26

References

1. Zhou R, Skibo EB..  (1996)  Chemistry of the pyrrolo[1,2-alpha]benzimidazole antitumor agents: influence of the 7-substituent on the ability to alkylate DNA and inhibit topoisomerase II.,  39  (21): [PMID:8863809] [10.1021/jm960064d]

2. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays