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

ID: ALA608451

Max Phase: Preclinical

Molecular Formula: C18H21N7O5

Molecular Weight: 415.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1cccc(/C=N/Nc2nc(N)c3ncn(C4O[C@H](CO)[C@@H](O)[C@H]4O)c3n2)c1

Standard InChI:  InChI=1S/C18H21N7O5/c1-29-10-4-2-3-9(5-10)6-21-24-18-22-15(19)12-16(23-18)25(8-20-12)17-14(28)13(27)11(7-26)30-17/h2-6,8,11,13-14,17,26-28H,7H2,1H3,(H3,19,22,23,24)/b21-6+/t11-,13-,14-,17?/m1/s1

Standard InChI Key:  FDTFZAAOFKDJCZ-UKDPARRBSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    8.2417   -6.0125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4917   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2292   -7.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4875   -4.9792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7917   -6.1750    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2375   -4.7292    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.9875   -8.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7125   -5.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1125   -4.9792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5917   -7.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7917   -4.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1125   -5.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917   -8.6167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9500   -7.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7375   -5.7667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4250   -6.1667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4750   -9.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7917   -3.7875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0500   -6.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6917   -9.2875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3500   -4.9125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3375   -5.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417   -4.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9417   -7.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6500   -3.6667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1542   -7.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -5.7292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6250   -6.1417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9167   -4.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667   -3.2625    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 28  2  0
 28 22  1  0
 29 27  1  0
 30 25  1  0
  6  4  1  0
 14 13  1  0
 11  9  1  0
 23 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA608451

   ---

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: 415.41

Molecular Weight (Monoisotopic): 415.1604

AlogP: -0.53

#Rotatable Bonds: 6

Polar Surface Area: 173.16

Molecular Species: NEUTRAL

HBA: 12

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 11.66

CX Basic pKa: 4.58

CX LogP: 0.26

CX LogD: 0.24

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.26

Np Likeness Score: 0.00

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