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

ID: ALA2326842

Max Phase: Preclinical

Molecular Formula: C17H18ClN7O4

Molecular Weight: 419.83

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N/N=C/c2ccc(Cl)cc2)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C17H18ClN7O4/c18-9-3-1-8(2-4-9)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:  CFRIPBAEDXQEHL-KFFALWPESA-N

Molfile:  

     RDKit          2D

 29 32  0  0  0  0  0  0  0  0999 V2000
    5.4560  -11.5630    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1553  -11.1361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1321  -10.3138    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4136   -9.9262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7381  -11.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7189  -10.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9323  -10.1155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4652  -10.7908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9633  -11.4436    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7290  -12.2265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9578  -12.5017    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9768  -13.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7598  -13.5530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2244  -12.8808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3915   -9.1093    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0414  -12.8631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0304  -14.3241    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3271  -13.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5730  -13.4995    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8736  -11.5259    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5702  -11.0987    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2885  -11.4885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9852  -11.0614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6993  -11.4538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3940  -11.0302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3766  -10.2128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6585   -9.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9577  -10.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0749   -9.7883    0.0000 Cl  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
 26 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2326842

   ---

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: 11.74

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: -0.11

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