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

ID: ALA17762

PubChem CID: 44271731

Max Phase: Preclinical

Molecular Formula: C18H21N3O5

Molecular Weight: 359.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCC(=O)OC1CCn2c1nc1c2C(=O)C(C)=C(NC(C)=O)C1=O

Standard InChI:  InChI=1S/C18H21N3O5/c1-4-5-6-12(23)26-11-7-8-21-15-14(20-18(11)21)17(25)13(19-10(3)22)9(2)16(15)24/h11H,4-8H2,1-3H3,(H,19,22)

Standard InChI Key:  HJXZLQMYRPWKPJ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   -0.2750  -10.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2833   -9.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5167  -10.9500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042   -9.6125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9917  -10.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7000   -9.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958  -11.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958   -9.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7000  -10.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7792  -10.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4208   -9.4625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0042  -11.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4417  -10.0375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7875  -11.3500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1333   -9.8792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958  -11.9292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2000  -10.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9958   -8.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1333  -10.7042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917  -11.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4208  -11.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8625   -9.8750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8458   -9.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167  -10.2042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792   -9.7167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0375  -10.0417    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  9  2  0
  7  1  1  0
  8  2  1  0
  9  7  1  0
 10  5  1  0
 11  6  1  0
 12  3  1  0
 13 10  1  0
 14 12  1  0
 15 11  1  0
 16  7  2  0
 17 13  1  0
 18  8  2  0
 19 15  2  0
 20 17  2  0
 21  9  1  0
 22 17  1  0
 23 15  1  0
 24 22  1  0
 25 24  1  0
 26 25  1  0
  5  4  2  0
  8  6  1  0
 14 10  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA17762

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

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: 359.38

Molecular Weight (Monoisotopic): 359.1481

AlogP: 1.85

#Rotatable Bonds: 5

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: 12.70

CX Basic pKa: 1.96

CX LogP: 0.40

CX LogD: 0.40

Aromatic Rings: 1

Heavy Atoms: 26

QED Weighted: 0.80

Np Likeness Score: 0.32

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