L-3'-amino-3'-deoxy-N6-methyladenosine-5'-N-methyluronamide

ID: ALA609872

PubChem CID: 16128913

Max Phase: Preclinical

Molecular Formula: C12H17N7O3

Molecular Weight: 307.31

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNC(=O)[C@@H]1O[C@H](n2cnc3c(NC)ncnc32)[C@@H](O)[C@H]1N

Standard InChI:  InChI=1S/C12H17N7O3/c1-14-9-6-10(17-3-16-9)19(4-18-6)12-7(20)5(13)8(22-12)11(21)15-2/h3-5,7-8,12,20H,13H2,1-2H3,(H,15,21)(H,14,16,17)/t5-,7+,8-,12+/m1/s1

Standard InChI Key:  YRQPFXUCXVGNQQ-GTPRZXKGSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    4.1230  -11.0179    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1218  -11.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8373  -12.2592    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8355  -10.6047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5514  -11.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5563  -11.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3489  -12.0984    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8339  -11.4226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3410  -10.7526    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8330   -9.7790    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1167   -9.3683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7559  -12.8111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5099  -13.5988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1766  -14.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8378  -13.5910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5795  -12.8120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1687  -14.9004    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7883  -14.0039    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6617  -13.5910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0746  -14.3060    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.0745  -12.8759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.9003  -14.3060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  1  0
 10 11  1  0
 12  7  1  1
 12 13  1  0
  2  3  1  0
  3  6  2  0
  1  2  2  0
  5  4  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 12  1  0
  6  7  1  0
 14 17  1  6
  7  8  1  0
 13 18  1  6
  8  9  2  0
 15 19  1  1
  9  5  1  0
 19 20  1  0
  4  1  1  0
 19 21  2  0
  4 10  1  0
 20 22  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA609872

   (2R,3R,4S,5S)-3-amino-4-hydroxy-N-methyl-5-[6-(methylamino)purin-9-yl]oxolane-2-carboxamide

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: 307.31

Molecular Weight (Monoisotopic): 307.1393

AlogP: -1.80

#Rotatable Bonds: 3

Polar Surface Area: 140.21

Molecular Species: NEUTRAL

HBA: 9

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.96

CX Basic pKa: 8.15

CX LogP: -2.16

CX LogD: -2.98

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.52

Np Likeness Score: 0.33

References

1. Kasiganesan H, Wright GL, Chiacchio MA, Gumina G..  (2009)  Novel l-adenosine analogs as cardioprotective agents.,  17  (14): [PMID:19502065] [10.1016/j.bmc.2008.12.011]

Source

Source(1):

• Scientific Literature