2-[6-Amino-2-(N'-thiophen-2-ylmethylene-hydrazino)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol

ID: ALA608176

Max Phase: Preclinical

Molecular Formula: C15H17N7O4S

Molecular Weight: 391.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N/N=C/c2cccs2)nc2c1ncn2C1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C15H17N7O4S/c16-12-9-13(20-15(19-12)21-18-4-7-2-1-3-27-7)22(6-17-9)14-11(25)10(24)8(5-23)26-14/h1-4,6,8,10-11,14,23-25H,5H2,(H3,16,19,20,21)/b18-4+/t8-,10-,11-,14?/m1/s1

Standard InChI Key:  CEBYJLIWMBILKB-OXISBLNKSA-N

Molfile:  

     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
    8.2792   -6.1375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5250   -5.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2625   -7.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5167   -5.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8292   -6.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2667   -4.8542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0167   -8.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7417   -5.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1417   -5.1042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6250   -7.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8292   -4.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1417   -5.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2250   -8.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9792   -7.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667   -5.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7667   -5.8917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2917   -5.0292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.0792   -6.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4542   -6.2917    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4917   -4.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667   -5.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5042   -9.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8250   -3.9125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7292   -9.4167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9792   -7.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875   -7.1875    0.0000 O   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 18  1  0
 16 19  1  0
 17 15  1  0
 18 16  2  0
 19 12  1  0
 20 17  1  0
 21 15  2  0
 22 21  1  0
  7 23  1  6
 24 11  1  0
 13 25  1  6
 14 26  1  1
 27 26  1  0
  6  4  1  0
 14 13  1  0
 11  9  1  0
 20 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA608176

   ---

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: 391.41

Molecular Weight (Monoisotopic): 391.1063

AlogP: -0.47

#Rotatable Bonds: 5

Polar Surface Area: 163.93

Molecular Species: NEUTRAL

HBA: 12

HBD: 5

#RO5 Violations: 1

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 10.52

CX Basic pKa: 4.57

CX LogP: 0.33

CX LogD: 0.30

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.29

Np Likeness Score: -0.38

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