2-(6-Benzylsulfanyl-8-propylamino-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3,4-diol

ID: ALA609378

PubChem CID: 46877166

Max Phase: Preclinical

Molecular Formula: C20H25N5O4S

Molecular Weight: 431.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCNc1nc2c(SCc3ccccc3)ncnc2n1C1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C20H25N5O4S/c1-2-8-21-20-24-14-17(25(20)19-16(28)15(27)13(9-26)29-19)22-11-23-18(14)30-10-12-6-4-3-5-7-12/h3-7,11,13,15-16,19,26-28H,2,8-10H2,1H3,(H,21,24)/t13-,15-,16-,19?/m1/s1

Standard InChI Key:  SQDWHYNKFJICLC-XAUNWSGPSA-N

Molfile:  

     RDKit          2D

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    0.6625    0.1208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792   -2.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6000   -0.3042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1792    0.7833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6125    0.5208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0833   -2.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5000   -1.5750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9125   -2.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1625   -2.0542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208    0.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208   -0.7167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0375    0.5208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3208    1.7583    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0375   -0.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4875    0.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4042   -3.5250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4125   -3.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6208    2.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1625   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2042    2.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9958   -1.2292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9000    0.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167    1.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6167    2.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7250    0.8458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375    1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4375    1.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250    2.8833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8417    2.1625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  1  1  0
  4  1  1  0
  5  2  2  0
  6  4  2  0
  7  3  1  0
  8  3  1  0
  9  7  1  0
 10  8  1  0
 11  6  1  0
 12  4  1  0
 13 15  1  0
 14 11  1  0
 15 12  2  0
 16  2  1  0
  7 17  1  6
  9 18  1  6
 19 14  1  0
 10 20  1  1
 21 19  1  0
 22 20  1  0
 23 16  1  0
 24 21  2  0
 25 21  1  0
 26 23  1  0
 27 26  1  0
 28 24  1  0
 29 25  2  0
 30 29  1  0
  6  5  1  0
 10  9  1  0
 11 13  2  0
 28 30  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA609378

   (3R,4S,5R)-2-[6-benzylsulfanyl-8-(propylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

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: 431.52

Molecular Weight (Monoisotopic): 431.1627

AlogP: 1.55

#Rotatable Bonds: 8

Polar Surface Area: 125.55

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 2.77

CX LogP: 2.02

CX LogD: 2.02

Aromatic Rings: 3

Heavy Atoms: 30

QED Weighted: 0.31

Np Likeness Score: -0.31

References

1. Tromp RA, Spanjersberg RF, von Frijtag Drabbe Künzel JK, IJzerman AP..  (2005)  Inhibition of nucleoside transport proteins by C8-alkylamine-substituted purines.,  48  (1): [PMID:15634027] [10.1021/jm049303k]

Source

Source(1):

• Scientific Literature