Acetic acid 6-acetylamino-7-methoxy-5,8-dioxo-2,3,5,8-tetrahydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-3-yl ester

ID: ALA137577

PubChem CID: 10735380

Max Phase: Preclinical

Molecular Formula: C15H15N3O6

Molecular Weight: 333.30

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC1=C(NC(C)=O)C(=O)c2nc3n(c2C1=O)CCC3OC(C)=O

Standard InChI:  InChI=1S/C15H15N3O6/c1-6(19)16-10-12(21)9-11(13(22)14(10)23-3)18-5-4-8(15(18)17-9)24-7(2)20/h8H,4-5H2,1-3H3,(H,16,19)

Standard InChI Key:  MPIKONQNGZXVAO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  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
    2.0792   -3.1542    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
    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
    2.4292   -2.6667    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
    3.0042   -2.8542    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
    2.4292   -3.6417    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
    0.9875   -3.8750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5708   -2.3750    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
    4.0375   -2.7375    0.0000 C   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
   -0.5708   -2.9750    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
   -1.0958   -2.0750    0.0000 C   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
   -0.0583   -3.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  8  2  0
  5  1  1  0
  6  2  1  0
  7  3  1  0
  8  5  1  0
  9  2  1  0
 10  7  1  0
 11  4  1  0
 12  3  1  0
 13 10  1  0
 14 12  1  0
 15  5  2  0
 16 11  1  0
 17  9  2  0
 18 13  1  0
 19  8  1  0
 20 16  2  0
 21 18  2  0
 22 16  1  0
 23 18  1  0
 24 19  1  0
  7  6  2  0
  9  4  1  0
 14 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA137577

   (6-acetamido-7-methoxy-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: 333.30

Molecular Weight (Monoisotopic): 333.0961

AlogP: 0.26

#Rotatable Bonds: 3

Polar Surface Area: 116.59

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.27

CX Basic pKa: 1.76

CX LogP: -1.99

CX LogD: -1.99

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.79

Np Likeness Score: 0.66

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