4-{[3-(2-Chloro-ethyl)-4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carbonyl]-amino}-isophthalamide

ID: ALA37881

PubChem CID: 10069812

Max Phase: Preclinical

Molecular Formula: C15H13ClN8O4

Molecular Weight: 404.77

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1ccc(NC(=O)c2ncn3c(=O)n(CCCl)nnc23)c(C(N)=O)c1

Standard InChI:  InChI=1S/C15H13ClN8O4/c16-3-4-24-15(28)23-6-19-10(13(23)21-22-24)14(27)20-9-2-1-7(11(17)25)5-8(9)12(18)26/h1-2,5-6H,3-4H2,(H2,17,25)(H2,18,26)(H,20,27)

Standard InChI Key:  SBZBUHMRZHMZSI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    5.8417   -6.9875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8375   -6.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0542   -5.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5542   -5.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5542   -7.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2667   -6.1625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2667   -6.9875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5667   -6.5792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0625   -7.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9667   -3.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7917   -5.1292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7667   -4.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9875   -4.9625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7500   -3.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2042   -4.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -2.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0542   -1.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5542   -8.2250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3417   -4.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3542   -3.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9792   -7.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875   -5.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417   -1.6292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1417   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5542   -3.7500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5917   -1.1500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6917   -8.6417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.9792   -8.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  2  0
  4  2  1  0
  5  1  1  0
  6  7  1  0
  7  5  1  0
  8  9  2  0
  9  1  1  0
 10 12  1  0
 11  3  1  0
 12 13  1  0
 13 11  1  0
 14 10  2  0
 15 10  1  0
 16 24  2  0
 17 16  1  0
 18  5  2  0
 19 11  2  0
 20 12  2  0
 21  7  1  0
 22 15  2  0
 23 17  2  0
 24 20  1  0
 25 15  1  0
 26 17  1  0
 27 28  1  0
 28 21  1  0
  3  8  1  0
  6  4  2  0
 14 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA37881

   4-[[3-(2-Chloroethyl)-4-oxoimidazo[5,1-d][1,2,3,5]tetrazine-8-carbonyl]amino]benzene-1,3-dicarboxamide

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: 404.77

Molecular Weight (Monoisotopic): 404.0748

AlogP: -1.03

#Rotatable Bonds: 6

Polar Surface Area: 180.36

Molecular Species: NEUTRAL

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 12

HBD (Lipinski): 5

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 12.57

CX Basic pKa: ┄

CX LogP: 0.97

CX LogD: 0.97

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.44

Np Likeness Score: -1.74

References

1. Clark AS, Deans B, Stevens MF, Tisdale MJ, Wheelhouse RT, Denny BJ, Hartley JA..  (1995)  Antitumor imidazotetrazines. 32. Synthesis of novel imidazotetrazinones and related bicyclic heterocycles to probe the mode of action of the antitumor drug temozolomide.,  38  (9): [PMID:7739008] [10.1021/jm00009a010]

Source

Source(1):

• Scientific Literature