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

ID: ALA286416

PubChem CID: 44279020

Max Phase: Preclinical

Molecular Formula: C13H12ClN7O2

Molecular Weight: 333.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(NNc1ccccc1)c1ncn2c(=O)n(CCCl)nnc12

Standard InChI:  InChI=1S/C13H12ClN7O2/c14-6-7-21-13(23)20-8-15-10(11(20)17-19-21)12(22)18-16-9-4-2-1-3-5-9/h1-5,8,16H,6-7H2,(H,18,22)

Standard InChI Key:  KOEDKJUSKVKXLC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    5.2750   -4.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750   -3.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7792   -3.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7292   -3.2042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7292   -4.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -3.4417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -4.0167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2750   -3.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5792   -4.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167   -2.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9875   -2.6542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7292   -4.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9292   -1.9750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9667   -2.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9000   -4.2875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917   -1.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7667   -4.3750    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.3042   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4917   -0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0792   -1.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667   -1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0792   -0.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6750   -0.8917    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  5  2  0
 13 11  1  0
 14 10  2  0
 15  7  1  0
 16 13  1  0
 17 18  1  0
 18 15  1  0
 19 16  1  0
 20 16  2  0
 21 20  1  0
 22 19  2  0
 23 21  2  0
  3  8  1  0
  4  6  2  0
 23 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA286416

   3-(2-chloroethyl)-4-oxo-N'-phenylimidazo[5,1-d][1,2,3,5]tetrazine-8-carbohydrazide

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: 333.74

Molecular Weight (Monoisotopic): 333.0741

AlogP: 0.28

#Rotatable Bonds: 5

Polar Surface Area: 106.21

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.86

CX Basic pKa: ┄

CX LogP: 2.48

CX LogD: 2.47

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.51

Np Likeness Score: -2.00

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