3-(4-{[6-Amino-9-(3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-hydrazonomethyl}-phenyl)-propionic acid

ID: ALA607604

Max Phase: Preclinical

Molecular Formula: C20H23N7O6

Molecular Weight: 457.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N/N=C/c2ccc(CCC(=O)O)cc2)nc2c1ncn2C1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C20H23N7O6/c21-17-14-18(27(9-22-14)19-16(32)15(31)12(8-28)33-19)25-20(24-17)26-23-7-11-3-1-10(2-4-11)5-6-13(29)30/h1-4,7,9,12,15-16,19,28,31-32H,5-6,8H2,(H,29,30)(H3,21,24,25,26)/b23-7+/t12-,15-,16-,19?/m1/s1

Standard InChI Key:  RMOLMLSFQKBAFR-VFWWHRCQSA-N

Molfile:  

     RDKit          2D

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    5.7250   -2.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4625   -4.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7167   -1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.9417   -1.9667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -1.5792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.8250   -4.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9667   -2.3667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1667    0.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.2792   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9292   -5.8917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5500   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5667   -2.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1542   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8792   -0.2667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1792   -3.6667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5583   -1.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8542   -2.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5792   -1.5125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1500   -2.3292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8667   -1.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3875   -3.6625    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
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 12  5  1  0
 13  7  1  0
 14 10  1  0
 15 17  1  0
 16 23  1  0
 17 12  1  0
 18 16  2  0
  7 19  1  6
 20 11  1  0
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 13 22  1  6
 23 28  1  0
 24 21  1  0
 25 32  2  0
 26 16  1  0
 14 27  1  1
 28 25  1  0
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 30 24  2  0
 31 29  2  0
 32 30  1  0
 33 27  1  0
  6  4  1  0
 14 13  1  0
 11  9  1  0
 31 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA607604

   ---

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: 457.45

Molecular Weight (Monoisotopic): 457.1710

AlogP: -0.52

#Rotatable Bonds: 8

Polar Surface Area: 201.23

Molecular Species: ACID

HBA: 12

HBD: 6

#RO5 Violations: 2

HBA (Lipinski): 13

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 4.22

CX Basic pKa: 4.81

CX LogP: -0.49

CX LogD: -2.54

Aromatic Rings: 3

Heavy Atoms: 33

QED Weighted: 0.19

Np Likeness Score: 0.19

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