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

ID: ALA31897

Cas Number: 113942-32-8

PubChem CID: 124241

Max Phase: Preclinical

Molecular Formula: C7H6ClN5O3

Molecular Weight: 243.61

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1ncn2c(=O)n(CCCl)nnc12

Standard InChI:  InChI=1S/C7H6ClN5O3/c8-1-2-13-7(16)12-3-9-4(6(14)15)5(12)10-11-13/h3H,1-2H2,(H,14,15)

Standard InChI Key:  FOGTXLLWVRUBDH-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 16 17  0  0  0  0  0  0  0  0999 V2000
    6.1500   -3.2792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1500   -2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5792   -2.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6750   -2.3792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -3.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917   -2.6792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917   -3.2792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2292   -2.9792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5792   -3.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3917   -1.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -4.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8042   -1.4667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7167   -3.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8042   -1.7917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.7542   -3.5875    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.2375   -3.2792    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  5  2  0
 12 10  2  0
 13  7  1  0
 14 10  1  0
 15 16  1  0
 16 13  1  0
  3  8  1  0
  4  6  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA31897

   3-(2-Chloroethyl)-4-oxoimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxylic acid

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: 243.61

Molecular Weight (Monoisotopic): 243.0159

AlogP: -0.78

#Rotatable Bonds: 3

Polar Surface Area: 102.38

Molecular Species: ACID

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.26

CX Basic pKa: ┄

CX LogP: 1.19

CX LogD: -2.24

Aromatic Rings: 2

Heavy Atoms: 16

QED Weighted: 0.71

Np Likeness Score: -1.62

References

1. Horspool KR, Stevens MF, Newton CG, Lunt E, Walsh RJ, Pedgrift BL, Baig GU, Lavelle F, Fizames C..  (1990)  Antitumor imidazotetrazines. 20. Preparation of the 8-acid derivative of mitozolomide and its utility in the preparation of active antitumor agents.,  33  (5): [PMID:2329560] [10.1021/jm00167a018]

2. 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]

3. Arrowsmith J, Jennings SA, Clark AS, Stevens MF..  (2002)  Antitumor imidazotetrazines. 41. Conjugation of the antitumor agents mitozolomide and temozolomide to peptides and lexitropsins bearing DNA major and minor groove-binding structural motifs.,  45  (25): [PMID:12459014] [10.1021/jm020936d]

Source

Source(1):

• Scientific Literature