Acetic acid 6-aziridin-1-yl-5,8-dioxo-2,3,5,8-tetrahydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-3-yl ester

ID: ALA137429

PubChem CID: 383412

Max Phase: Preclinical

Molecular Formula: C14H13N3O4

Molecular Weight: 287.27

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC1CCn2c1nc1c2C(=O)C=C(N2CC2)C1=O

Standard InChI:  InChI=1S/C14H13N3O4/c1-7(18)21-10-2-3-17-12-9(19)6-8(16-4-5-16)13(20)11(12)15-14(10)17/h6,10H,2-5H2,1H3

Standard InChI Key:  IKYRZJWIDHPKIN-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 24  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
    2.0792   -3.1542    0.0000 N   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
    2.4292   -2.6667    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   -2.0667    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   -3.2750    0.0000 C   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
    3.0042   -2.8542    0.0000 C   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
   -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
    3.4875   -2.4917    0.0000 O   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
    4.0375   -2.7375    0.0000 C   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
    0.9875   -3.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1000   -3.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5167   -2.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  1  1  0
  5  4  2  0
  6  7  1  0
  7  1  1  0
  8  6  2  0
  9  2  1  0
 10  6  1  0
 11  5  1  0
 12  3  1  0
 13 10  1  0
 14 10  1  0
 15 11  1  0
 16 11  1  0
 17 15  1  0
 18  7  2  0
 19  9  2  0
 20 17  2  0
 21 17  1  0
  5  3  1  0
  8  9  1  0
 13 14  1  0
 12 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA137429

   [6-(aziridin-1-yl)-5,8-dioxo-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazol-3-yl] acetate

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: 287.27

Molecular Weight (Monoisotopic): 287.0906

AlogP: 0.47

#Rotatable Bonds: 2

Polar Surface Area: 81.27

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.98

CX LogP: -0.76

CX LogD: -0.76

Aromatic Rings: 1

Heavy Atoms: 21

QED Weighted: 0.58

Np Likeness Score: 0.64

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