2-{6-Amino-2-[N'-(3-chloro-benzylidene)-hydrazino]-purin-9-yl}-5-hydroxymethyl-tetrahydro-furan-3,4-diol

ID: ALA607605

Max Phase: Preclinical

Molecular Formula: C17H18ClN7O4

Molecular Weight: 419.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N/N=C/c2cccc(Cl)c2)nc2c1ncn2C1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C17H18ClN7O4/c18-9-3-1-2-8(4-9)5-21-24-17-22-14(19)11-15(23-17)25(7-20-11)16-13(28)12(27)10(6-26)29-16/h1-5,7,10,12-13,16,26-28H,6H2,(H3,19,22,23,24)/b21-5+/t10-,12-,13-,16?/m1/s1

Standard InChI Key:  HOPZBZQQAOAGTC-PSOSHUPLSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    8.3042   -6.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5542   -5.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2917   -7.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5500   -5.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8542   -6.2042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.3000   -4.7542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0500   -8.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7750   -5.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1750   -5.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6542   -7.4292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8542   -4.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1750   -5.8042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2542   -8.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125   -7.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8000   -5.7917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4875   -6.2000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.5417   -9.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8542   -3.8167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1125   -6.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7542   -9.3167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4125   -4.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4000   -5.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7042   -4.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -7.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7125   -3.7000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.2167   -7.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -5.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -4.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6875   -6.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  2  1  0
  5  2  2  0
  6  8  2  0
  7  3  1  0
  8  1  1  0
  9 12  2  0
 10  3  1  0
 11  4  2  0
 12  5  1  0
 13  7  1  0
 14 10  1  0
 15 16  1  0
 16 12  1  0
  7 17  1  6
 18 11  1  0
 19 15  2  0
 13 20  1  6
 21 22  2  0
 22 19  1  0
 23 21  1  0
 14 24  1  1
 25 23  1  0
 26 24  1  0
 27 29  2  0
 28 27  1  0
 29 22  1  0
  6  4  1  0
 14 13  1  0
 11  9  1  0
 23 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA607605

   ---

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: 419.83

Molecular Weight (Monoisotopic): 419.1109

AlogP: 0.12

#Rotatable Bonds: 5

Polar Surface Area: 163.93

Molecular Species: NEUTRAL

HBA: 11

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.68

CX Basic pKa: 4.58

CX LogP: 1.02

CX LogD: 1.00

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.29

Np Likeness Score: -0.20

References

1. Niiya K, Thompson RD, Silvia SK, Olsson RA..  (1992)  2-(N'-aralkylidenehydrazino)adenosines: potent and selective coronary vasodilators.,  35  (24): [PMID:1469688] [10.1021/jm00102a008]

Source

Source(1):

• Scientific Literature