3-(2-Chloro-ethyl)-4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid (3-carbamoyl-phenyl)-amide

ID: ALA37801

PubChem CID: 10248058

Max Phase: Preclinical

Molecular Formula: C14H12ClN7O3

Molecular Weight: 361.75

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(=O)c1cccc(NC(=O)c2ncn3c(=O)n(CCCl)nnc23)c1

Standard InChI:  InChI=1S/C14H12ClN7O3/c15-4-5-22-14(25)21-7-17-10(12(21)19-20-22)13(24)18-9-3-1-2-8(6-9)11(16)23/h1-3,6-7H,4-5H2,(H2,16,23)(H,18,24)

Standard InChI Key:  ZYVUIFQOUBJFHE-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  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
    4.7917   -5.1292    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
    1.9917   -2.8042    0.0000 C   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
    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
    3.7667   -4.1625    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
    7.9792   -7.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3250   -3.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -1.9875    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
    3.3375   -2.5542    0.0000 C   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
    7.9792   -8.2292    0.0000 C   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
  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  3  1  0
 11 10  1  0
 12 13  1  0
 13 17  2  0
 14  5  2  0
 15 10  2  0
 16 11  1  0
 17 16  1  0
 18  7  1  0
 19 12  2  0
 20 12  1  0
 21 24  1  0
 22 23  2  0
 23 25  1  0
 24 18  1  0
 25 16  2  0
  3  8  1  0
  6  4  2  0
 13 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA37801

   N-(3-carbamoylphenyl)-3-(2-chloroethyl)-4-oxoimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

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: 361.75

Molecular Weight (Monoisotopic): 361.0690

AlogP: -0.12

#Rotatable Bonds: 5

Polar Surface Area: 137.27

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.46

CX Basic pKa: ┄

CX LogP: 1.47

CX LogD: 1.47

Aromatic Rings: 3

Heavy Atoms: 25

QED Weighted: 0.61

Np Likeness Score: -2.02

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