Chloro-acetic acid 6-aziridin-1-yl-7-methyl-5,8-dioxo-2,3,5,8-tetrahydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-3-yl ester

ID: ALA417090

PubChem CID: 374006

Max Phase: Preclinical

Molecular Formula: C15H14ClN3O4

Molecular Weight: 335.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1=C(N2CC2)C(=O)c2nc3n(c2C1=O)CCC3OC(=O)CCl

Standard InChI:  InChI=1S/C15H14ClN3O4/c1-7-11(18-4-5-18)14(22)10-12(13(7)21)19-3-2-8(15(19)17-10)23-9(20)6-16/h8H,2-6H2,1H3

Standard InChI Key:  PNJHXCRCPJOGIV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 26  0  0  0  0  0  0  0  0999 V2000
    0.7292   -6.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7292   -7.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5250   -7.9125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5125   -6.5750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0167   -6.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -7.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6958   -6.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6958   -7.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0167   -8.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4083   -6.4250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7875   -7.4875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -8.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8333   -5.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2333   -6.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4500   -7.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -8.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0167   -5.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0167   -8.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2042   -7.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3000   -8.1500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4083   -8.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6292   -7.1667    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    4.8667   -6.8375    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  1  1  0
  6  4  2  0
  7  5  1  0
  8  7  2  0
  9  2  1  0
 10  7  1  0
 11  6  1  0
 12  3  1  0
 13 10  1  0
 14 10  1  0
 15 11  1  0
 16 11  1  0
 17  5  2  0
 18  9  2  0
 19 15  1  0
 20 19  2  0
 21  8  1  0
 22 23  1  0
 23 19  1  0
  6  3  1  0
  9  8  1  0
 13 14  1  0
 12 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA417090

   [6-(aziridin-1-yl)-7-methyl-5,8-dioxo-2,3-dihydro-1H-pyrrolo[1,2-a]benzimidazol-3-yl] 2-chloroacetate

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: 335.75

Molecular Weight (Monoisotopic): 335.0673

AlogP: 1.08

#Rotatable Bonds: 3

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: 1.96

CX LogP: 0.17

CX LogD: 0.17

Aromatic Rings: 1

Heavy Atoms: 23

QED Weighted: 0.47

Np Likeness Score: 0.22

References

1. Schulz WG, Islam I, Skibo EB..  (1995)  Pyrrolo[1,2-a]benzimidazole-based quinones and iminoquinones. The role of the 3-substituent on cytotoxicity.,  38  (1): [PMID:7837221] [10.1021/jm00001a016]

2. PubChem BioAssay data set, 

Source

Source(2):

• Scientific Literature
• PubChem BioAssays