2-(6-Amino-2-{N'-[1-(4-fluoro-phenyl)-ethylidene]-hydrazino}-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

ID: ALA608174

Max Phase: Preclinical

Molecular Formula: C18H20FN7O4

Molecular Weight: 417.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C/C(=N\Nc1nc(N)c2ncn(C3O[C@H](CO)[C@@H](O)[C@H]3O)c2n1)c1ccc(F)cc1

Standard InChI:  InChI=1S/C18H20FN7O4/c1-8(9-2-4-10(19)5-3-9)24-25-18-22-15(20)12-16(23-18)26(7-21-12)17-14(29)13(28)11(6-27)30-17/h2-5,7,11,13-14,17,27-29H,6H2,1H3,(H3,20,22,23,25)/b24-8+/t11-,13-,14-,17?/m1/s1

Standard InChI Key:  DOQXNVBLKUFUIH-WGVRSDFZSA-N

Molfile:  

     RDKit          2D

 30 33  0  0  0  0  0  0  0  0999 V2000
    6.7250   -2.5417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9667   -2.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -4.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9667   -1.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750   -2.7042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7167   -1.2625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4625   -5.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1917   -1.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917   -1.5167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0667   -3.9292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2750   -1.1167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5917   -2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6667   -5.1542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4292   -4.3917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2167   -2.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9000   -2.7042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5292   -2.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8167   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9542   -5.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2667   -0.3250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8250   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0917   -2.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1667   -5.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3917   -1.4292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3875   -2.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125   -1.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4250   -3.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208   -1.0042    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.6292   -3.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5167   -3.5125    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
 17 15  2  0
 18 17  1  0
  7 19  1  6
 20 11  1  0
 21 18  2  0
 22 18  1  0
 13 23  1  6
 24 25  1  0
 25 22  2  0
 26 21  1  0
 14 27  1  1
 28 24  1  0
 29 27  1  0
 30 17  1  0
  6  4  1  0
 14 13  1  0
 11  9  1  0
 26 24  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA608174

   ---

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: 417.40

Molecular Weight (Monoisotopic): 417.1561

AlogP: 0.00

#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: 11.45

CX Basic pKa: 4.57

CX LogP: 0.40

CX LogD: 0.39

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.28

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]

Source

Source(1):

• Scientific Literature