Acetic acid 7-acetoxy-4,9-dioxo-2,3,4,6,7,9-hexahydro-1H,5H-3a,4b,8,10-tetraaza-dicyclopenta[a,h]-s-indacen-1-yl ester

ID: ALA405158

PubChem CID: 44371836

Max Phase: Preclinical

Molecular Formula: C18H16N4O6

Molecular Weight: 384.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)OC1CCn2c1nc1c2C(=O)c2c(nc3n2CCC3OC(C)=O)C1=O

Standard InChI:  InChI=1S/C18H16N4O6/c1-7(23)27-9-3-5-21-13-11(19-17(9)21)15(25)12-14(16(13)26)22-6-4-10(18(22)20-12)28-8(2)24/h9-10H,3-6H2,1-2H3

Standard InChI Key:  YUJREGITCKITCF-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 32  0  0  0  0  0  0  0  0999 V2000
    4.4167   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8500   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8500   -3.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4167   -3.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -4.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6292   -4.7625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -4.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6292   -3.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6375   -3.4292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1167   -4.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1542   -4.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -3.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3667   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9042   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1167   -5.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1500   -5.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5875   -3.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6792   -3.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9042   -5.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3625   -5.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -5.7417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1292   -2.4417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3417   -4.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542   -3.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0667   -2.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4125   -5.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.0167   -3.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5000   -2.6917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  7  1  0
  3  2  2  0
  4  1  2  0
  5  1  1  0
  6  2  1  0
  7  1  1  0
  8  3  1  0
  9  4  1  0
 10  6  1  0
 11  5  1  0
 12  4  1  0
 13 11  1  0
 14 10  1  0
 15  6  1  0
 16  5  1  0
 14 17  1  0
 13 18  1  0
 19 15  1  0
 20 16  1  0
 21  7  2  0
 22 12  2  0
 23 17  1  0
 24 18  1  0
 25 24  2  0
 26 23  2  0
 27 23  1  0
 28 24  1  0
  9 11  2  0
  3 12  1  0
 13 20  1  0
 10  8  2  0
 19 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA405158

   (15-Acetyloxy-2,11-dioxo-4,9,13,18-tetrazapentacyclo[10.6.0.03,10.04,8.014,18]octadeca-1(12),3(10),8,13-tetraen-7-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: 384.35

Molecular Weight (Monoisotopic): 384.1070

AlogP: 0.87

#Rotatable Bonds: 2

Polar Surface Area: 122.38

Molecular Species: NEUTRAL

HBA: 10

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.11

CX LogP: -0.56

CX LogD: -0.56

Aromatic Rings: 2

Heavy Atoms: 28

QED Weighted: 0.60

Np Likeness Score: 0.57

References

1. Schulz WG, Skibo EB..  (2000)  Inhibitors of topoisomerase II based on the benzodiimidazole and dipyrroloimidazobenzimidazole ring systems: controlling DT-diaphorase reductive inactivation with steric bulk.,  43  (4): [PMID:10691689] [10.1021/jm990210q]

Source

Source(1):

• Scientific Literature