2-(3-p-nitrophenyloxycarbonyl-3-methyltriazen-1-yl)-6-benzyloxypurine

ID: ALA387940

PubChem CID: 11408262

Max Phase: Preclinical

Molecular Formula: C20H16N8O5

Molecular Weight: 448.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CN(/N=N/c1nc(OCc2ccccc2)c2nc[nH]c2n1)C(=O)Oc1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C20H16N8O5/c1-27(20(29)33-15-9-7-14(8-10-15)28(30)31)26-25-19-23-17-16(21-12-22-17)18(24-19)32-11-13-5-3-2-4-6-13/h2-10,12H,11H2,1H3,(H,21,22,23,24)/b26-25+

Standard InChI Key:  YUJWQSHNZAQYRG-OCEACIFDSA-N

Molfile:  

     RDKit          2D

 33 36  0  0  0  0  0  0  0  0999 V2000
    2.3569  -15.0333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3557  -15.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0706  -16.2735    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0688  -14.6205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7841  -15.0297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7844  -15.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5749  -16.1173    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0632  -15.4448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5744  -14.7727    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0663  -13.7955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7795  -13.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7771  -12.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4958  -12.1437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4936  -11.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7774  -10.9084    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0618  -11.3273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0674  -12.1502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6409  -16.2726    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9268  -15.8595    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2120  -16.2715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5021  -15.8584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2169  -16.2703    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5015  -15.0334    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2114  -17.0965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9311  -15.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9254  -15.0343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6387  -14.6213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3545  -15.0333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3525  -15.8626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6386  -16.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0709  -14.6218    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7852  -15.0347    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0714  -13.7968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 15 16  1  0
  6  7  1  0
 16 17  2  0
 17 12  1  0
  7  8  1  0
  2 18  1  0
  8  9  2  0
 18 19  2  0
  9  5  1  0
 19 20  1  0
  4  1  1  0
 20 21  1  0
  4 10  1  0
 21 22  1  0
  5  6  1  0
 21 23  2  0
 10 11  1  0
 20 24  1  0
 22 25  1  0
 11 12  1  0
 25 26  2  0
  2  3  1  0
 26 27  1  0
 12 13  2  0
 27 28  2  0
  3  6  2  0
 28 29  1  0
 13 14  1  0
 29 30  2  0
 30 25  1  0
  1  2  2  0
 14 15  2  0
  5  4  2  0
 31 32  2  0
 31 33  1  0
 28 31  1  0
M  CHG  2  31   1  33  -1
M  END

Alternative Forms

1. Parent:

   

   ALA387940

   6-Benzyloxy-2-[3-(4-nitrophenyloxycarbonyl)-3-methyl-triazen e-1-yl]-purine

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: 448.40

Molecular Weight (Monoisotopic): 448.1244

AlogP: 3.97

#Rotatable Bonds: 7

Polar Surface Area: 161.09

Molecular Species: NEUTRAL

HBA: 10

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 13

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 8.71

CX Basic pKa: ┄

CX LogP: 4.92

CX LogD: 4.90

Aromatic Rings: 4

Heavy Atoms: 33

QED Weighted: 0.25

Np Likeness Score: -0.91

References

1. Wanner MJ, Koch M, Koomen GJ..  (2004)  Synthesis and antitumor activity of methyltriazene prodrugs simultaneously releasing DNA-methylating agents and the antiresistance drug O(6)-benzylguanine.,  47  (27): [PMID:15615536] [10.1021/jm049556d]

Source

Source(1):

• Scientific Literature