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

ID: ALA2326828

Max Phase: Preclinical

Molecular Formula: C18H21N7O5

Molecular Weight: 415.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(/C=N/Nc2nc(N)c3ncn([C@@H]4O[C@H](CO)[C@@H](O)[C@H]4O)c3n2)cc1

Standard InChI:  InChI=1S/C18H21N7O5/c1-29-10-4-2-9(3-5-10)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:  UKEASMXMANFUQZ-DXALFEDPSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    5.4271  -19.7515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1264  -19.3245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1032  -18.5022    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.3847  -18.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7092  -19.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6900  -18.5394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9034  -18.3039    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4364  -18.9793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9344  -19.6320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7001  -20.4149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9289  -20.6901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9479  -21.5071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7309  -21.7414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1955  -21.0692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3626  -17.2978    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0125  -21.0516    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0015  -22.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2982  -22.0027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5441  -21.6879    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8447  -19.7143    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5413  -19.2872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2596  -19.6769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9563  -19.2498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6704  -19.6422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3651  -19.2186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3477  -18.4013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6296  -18.0093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9288  -18.4347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0431  -17.9785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0246  -17.1616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
 10  9  1  1
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
  4 15  1  0
 14 16  1  6
 13 17  1  6
 12 18  1  1
 18 19  1  0
  2 20  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 23 28  2  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 29 30  1  0
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2326828

   ---

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: 11.84

CX Basic pKa: 4.70

CX LogP: 0.26

CX LogD: 0.24

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.26

Np Likeness Score: 0.07

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]

2. El-Tayeb A, Gollos S..  (2013)  Synthesis and structure-activity relationships of 2-hydrazinyladenosine derivatives as A(2A) adenosine receptor ligands.,  21  (2): [PMID:23245803] [10.1016/j.bmc.2012.11.021]

Source

Source(1):

• Scientific Literature