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

ID: ALA607891

Max Phase: Preclinical

Molecular Formula: C19H23N7O4

Molecular Weight: 413.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N/N=C/CCc2ccccc2)nc2c1ncn2C1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C19H23N7O4/c20-16-13-17(26(10-21-13)18-15(29)14(28)12(9-27)30-18)24-19(23-16)25-22-8-4-7-11-5-2-1-3-6-11/h1-3,5-6,8,10,12,14-15,18,27-29H,4,7,9H2,(H3,20,23,24,25)/b22-8+/t12-,14-,15-,18?/m1/s1

Standard InChI Key:  CEULIZARKMXCMY-LRSBOZTDSA-N

Molfile:  

     RDKit          2D

 30 33  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
    5.4875   -6.2000    0.0000 N   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
    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
    6.7542   -9.3167    0.0000 O   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
    7.0042   -7.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9667   -5.7542    0.0000 C   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
    3.4000   -5.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6792   -6.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792   -4.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2625   -6.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5500   -5.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2750   -4.5042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5542   -4.9125    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 12  1  0
 16 15  1  0
  7 17  1  6
 18 11  1  0
 13 19  1  6
 20 16  2  0
 14 21  1  1
 22 25  1  0
 23 21  1  0
 24 20  1  0
 25 24  1  0
 26 22  2  0
 27 22  1  0
 28 27  2  0
 29 26  1  0
 30 28  1  0
  6  4  1  0
 14 13  1  0
 11  9  1  0
 29 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA607891

   ---

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: 413.44

Molecular Weight (Monoisotopic): 413.1812

AlogP: 0.05

#Rotatable Bonds: 7

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: 11.90

CX Basic pKa: 4.81

CX LogP: 0.63

CX LogD: 0.61

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.27

Np Likeness Score: 0.41

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