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

ID: ALA609662

PubChem CID: 46877168

Max Phase: Preclinical

Molecular Formula: C18H21N5O4S

Molecular Weight: 403.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CNc1nc2c(SCc3ccccc3)ncnc2n1C1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C18H21N5O4S/c1-19-18-22-12-15(23(18)17-14(26)13(25)11(7-24)27-17)20-9-21-16(12)28-8-10-5-3-2-4-6-10/h2-6,9,11,13-14,17,24-26H,7-8H2,1H3,(H,19,22)/t11-,13-,14-,17?/m1/s1

Standard InChI Key:  KKNJFNBLFLWUJS-IKYDMHQPSA-N

Molfile:  

     RDKit          2D

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   -0.3958   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3875    0.8708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1167   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2875   -1.4875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7000   -2.7542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.8250    0.6000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125    1.8375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8250   -0.2167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7000    0.2125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4167    2.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7833   -1.1417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1125    0.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8167    1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8167    2.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6375    2.9625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    2.2500    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
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  9  7  1  0
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 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
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  6  5  1  0
 10  9  1  0
 11 13  2  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA609662

   (3R,4S,5R)-2-[6-benzylsulfanyl-8-(methylamino)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: 403.46

Molecular Weight (Monoisotopic): 403.1314

AlogP: 0.77

#Rotatable Bonds: 6

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: 1.14

CX LogD: 1.14

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.35

Np Likeness Score: -0.11

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