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

ID: ALA287430

PubChem CID: 44278760

Max Phase: Preclinical

Molecular Formula: C9H10Cl2N6O2

Molecular Weight: 305.13

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C9H10Cl2N6O2/c10-1-3-12-8(18)6-7-14-15-17(4-2-11)9(19)16(7)5-13-6/h5H,1-4H2,(H,12,18)

Standard InChI Key:  ARGGCNRLHWIBRS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 19 20  0  0  0  0  0  0  0  0999 V2000
    5.1625   -4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.1625   -3.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917   -3.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6875   -3.2250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -4.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3667   -3.5000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3667   -4.1542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2417   -3.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5875   -4.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4042   -2.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6792   -5.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8125   -2.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0167   -4.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -2.6375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0167   -4.5625    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    3.8625   -1.0417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.4875   -4.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6292   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417   -1.6167    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 17  1  0
 16 19  1  0
 17 13  1  0
 18 14  1  0
 19 18  1  0
  3  8  1  0
  4  6  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA287430

   N,3-bis(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: 305.13

Molecular Weight (Monoisotopic): 304.0242

AlogP: -0.51

#Rotatable Bonds: 5

Polar Surface Area: 94.18

Molecular Species: NEUTRAL

HBA: 7

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.96

CX Basic pKa: ┄

CX LogP: 1.27

CX LogD: 1.27

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.75

Np Likeness Score: -1.77

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]

Source

Source(1):

• Scientific Literature