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

ID: ALA2113592

Max Phase: Preclinical

Molecular Formula: C15H23N7O4

Molecular Weight: 365.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)C/C=N/Nc1nc(N)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1

Standard InChI:  InChI=1S/C15H23N7O4/c1-7(2)3-4-18-21-15-19-12(16)9-13(20-15)22(6-17-9)14-11(25)10(24)8(5-23)26-14/h4,6-8,10-11,14,23-25H,3,5H2,1-2H3,(H3,16,19,20,21)/b18-4+/t8-,10-,11-,14-/m1/s1

Standard InChI Key:  XXRIESUTDBVRGJ-IDVJSUKHSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    5.7095   -4.4546    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9289   -4.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6922   -6.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9203   -3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2088   -4.6228    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6966   -3.1221    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4378   -7.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1882   -3.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4973   -3.3894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0324   -5.8906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2088   -2.9755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4973   -4.2088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6184   -7.1541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3641   -6.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7858   -4.6184    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0742   -4.1959    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9424   -7.8527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2045   -2.1519    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1053   -7.8527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3627   -4.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3641   -5.5499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5447   -5.5413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6253   -4.1700    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1164   -4.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8495   -4.1441    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1250   -5.4378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  1
  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 21  1  0
 23 20  1  0
 24 23  1  0
 25 24  1  0
 26 24  1  0
  6  4  1  0
 14 13  1  0
 11  9  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA2113592

   ---

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: 365.39

Molecular Weight (Monoisotopic): 365.1812

AlogP: -0.54

#Rotatable Bonds: 6

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: 4.79

CX LogP: -0.22

CX LogD: -0.24

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.33

Np Likeness Score: 0.61

References

1. van Tilburg EW, von Frijtag Drabbe Kunzel J, de Groote M, IJzerman AP..  (2002)  2,5'-Disubstituted adenosine derivatives: evaluation of selectivity and efficacy for the adenosine A(1), A(2A), and A(3) receptor.,  45  (2): [PMID:11784146] [10.1021/jm010952v]

2. Niiya K, Olsson RA, Thompson RD, Silvia SK, Ueeda M..  (1992)  2-(N'-alkylidenehydrazino)adenosines: potent and selective coronary vasodilators.,  35  (24): [PMID:1469687] [10.1021/jm00102a007]

Source

Source(1):

• Scientific Literature