N-[3-(2-Methoxy-acetyl)-7-methyl-5,8-dioxo-2,3,5,8-tetrahydro-1H-benzo[d]pyrrolo[1,2-a]imidazol-6-yl]-acetamide

ID: ALA277550

PubChem CID: 44271719

Max Phase: Preclinical

Molecular Formula: C16H17N3O5

Molecular Weight: 331.33

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COCC(=O)C1CCn2c1nc1c2C(=O)C(C)=C(NC(C)=O)C1=O

Standard InChI:  InChI=1S/C16H17N3O5/c1-7-11(17-8(2)20)15(23)12-13(14(7)22)19-5-4-9(16(19)18-12)10(21)6-24-3/h9H,4-6H2,1-3H3,(H,17,20)

Standard InChI Key:  LKIISDMVFZATAV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    5.1042   -6.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1042   -5.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9000   -6.9917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3792   -6.3250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8875   -5.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -5.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -7.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -5.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6792   -6.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1625   -6.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -5.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3875   -7.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1667   -7.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8250   -6.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -5.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -7.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3917   -4.6750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -6.7500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7292   -5.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -7.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5792   -6.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2417   -5.9167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5375   -5.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0042   -6.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  3  1  0
  5  2  1  0
  6  9  2  0
  7  1  1  0
  8  2  1  0
  9  7  1  0
 10  4  1  0
 11  6  1  0
 12  3  1  0
 13 12  1  0
 14 10  1  0
 15 11  1  0
 16  7  2  0
 17  8  2  0
 18 15  2  0
 19 14  2  0
 20  9  1  0
 21 14  1  0
 22 21  1  0
 23 15  1  0
 24 22  1  0
  8  6  1  0
  4  5  2  0
 13 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA277550

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

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: 331.33

Molecular Weight (Monoisotopic): 331.1168

AlogP: 0.37

#Rotatable Bonds: 4

Polar Surface Area: 107.36

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.67

CX Basic pKa: 2.43

CX LogP: -0.80

CX LogD: -0.80

Aromatic Rings: 1

Heavy Atoms: 24

QED Weighted: 0.85

Np Likeness Score: -0.14

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]

Source

Source(1):

• Scientific Literature