2-[6-Amino-2-(N'-naphthalen-1-ylmethylene-hydrazino)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol

ID: ALA608175

Max Phase: Preclinical

Molecular Formula: C21H21N7O4

Molecular Weight: 435.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N/N=C/c2cccc3ccccc23)nc2c1ncn2C1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C21H21N7O4/c22-18-15-19(28(10-23-15)20-17(31)16(30)14(9-29)32-20)26-21(25-18)27-24-8-12-6-3-5-11-4-1-2-7-13(11)12/h1-8,10,14,16-17,20,29-31H,9H2,(H3,22,25,26,27)/b24-8+/t14-,16-,17-,20?/m1/s1

Standard InChI Key:  BUYDXKBPOOYHPY-SHTSFZPOSA-N

Molfile:  

     RDKit          2D

 32 36  0  0  0  0  0  0  0  0999 V2000
    7.8667   -5.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.1167   -5.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8542   -7.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1125   -4.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4167   -6.0500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.8625   -4.6042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6125   -8.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3375   -5.2417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7375   -4.8542    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2167   -7.2750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4167   -4.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7375   -5.6542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8167   -8.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5750   -7.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3625   -5.6417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.0500   -6.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750   -4.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9625   -5.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1000   -9.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4167   -3.6625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6750   -6.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3167   -9.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2542   -4.3667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5667   -6.9417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7792   -6.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5375   -5.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2417   -6.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6917   -4.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5417   -4.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667   -3.5417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7000   -3.5542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9875   -3.1292    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 18  1  0
 18 21  1  0
  7 19  1  6
 20 11  1  0
 21 15  2  0
 13 22  1  6
 23 17  2  0
 14 24  1  1
 25 24  1  0
 26 27  1  0
 27 18  2  0
 28 17  1  0
 29 26  2  0
 30 23  1  0
 31 28  2  0
 32 31  1  0
  6  4  1  0
 14 13  1  0
 11  9  1  0
 29 23  1  0
 30 32  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA608175

   ---

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: 435.44

Molecular Weight (Monoisotopic): 435.1655

AlogP: 0.62

#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: 11.58

CX Basic pKa: 4.71

CX LogP: 1.40

CX LogD: 1.39

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.22

Np Likeness Score: -0.03

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