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

ID: ALA137025

PubChem CID: 10680910

Max Phase: Preclinical

Molecular Formula: C12H11N3O2

Molecular Weight: 229.24

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C1C=C(N2CC2)C(=O)c2c1nc1n2CCC1

Standard InChI:  InChI=1S/C12H11N3O2/c16-8-6-7(14-4-5-14)12(17)11-10(8)13-9-2-1-3-15(9)11/h6H,1-5H2

Standard InChI Key:  RZERNUWWSGYWRV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 20  0  0  0  0  0  0  0  0999 V2000
    1.5042   -2.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5042   -2.3667    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
    2.0667   -2.1792    0.0000 N   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
    2.0792   -3.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0583   -3.2750    0.0000 N   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
    2.4292   -2.6667    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
   -0.6583   -3.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3583   -3.7917    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
    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
  2  1  2  0
  3  1  1  0
  4  2  1  0
  5  3  1  0
  6  1  1  0
  7  5  1  0
  8  5  2  0
  9  6  1  0
 10  2  1  0
 11  7  1  0
 12  7  1  0
 13  3  2  0
 14 10  2  0
 15  6  1  0
 16  9  1  0
 17 15  1  0
  9  4  2  0
 10  8  1  0
 17 16  1  0
 11 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA137025

   7-(aziridin-1-yl)-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: 229.24

Molecular Weight (Monoisotopic): 229.0851

AlogP: 0.41

#Rotatable Bonds: 1

Polar Surface Area: 54.97

Molecular Species: NEUTRAL

HBA: 5

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.21

CX LogP: -0.26

CX LogD: -0.26

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.65

Np Likeness Score: -0.13

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]

Source

Source(1):

• Scientific Literature