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

ID: ALA609338

Max Phase: Preclinical

Molecular Formula: C17H18ClN7O4

Molecular Weight: 419.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N/N=C/c2ccccc2Cl)nc2c1ncn2C1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C17H18ClN7O4/c18-9-4-2-1-3-8(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:  BTHGHNBTEPTUHZ-PSOSHUPLSA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    8.7417   -6.3417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9917   -6.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8542   -7.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9875   -5.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2917   -6.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7375   -5.0542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6000   -8.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2125   -5.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6125   -5.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1875   -7.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2917   -4.9167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6125   -6.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7750   -8.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5250   -7.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2375   -6.0917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8375   -6.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9250   -6.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.8500   -5.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500   -6.4792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0875   -9.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2917   -4.1167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2917   -9.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5667   -4.8417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    5.7417   -7.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1250   -7.9667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1250   -6.4667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -4.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167   -6.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4167   -5.2292    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 17  1  0
 16 19  1  0
 17 12  1  0
 18 16  2  0
 19 15  2  0
  7 20  1  6
 21 11  1  0
 13 22  1  6
 23 18  1  0
 14 24  1  1
 25 24  1  0
 26 16  1  0
 27 18  1  0
 28 26  2  0
 29 28  1  0
  6  4  1  0
 14 13  1  0
 11  9  1  0
 27 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA609338

   ---

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: 11.34

CX Basic pKa: 4.57

CX LogP: 1.02

CX LogD: 1.00

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.29

Np Likeness Score: -0.18

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