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

ID: ALA609377

PubChem CID: 46877165

Max Phase: Preclinical

Molecular Formula: C19H23N5O4S

Molecular Weight: 417.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCNc1nc2c(SCc3ccccc3)ncnc2n1C1O[C@H](CO)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C19H23N5O4S/c1-2-20-19-23-13-16(24(19)18-15(27)14(26)12(8-25)28-18)21-10-22-17(13)29-9-11-6-4-3-5-7-11/h3-7,10,12,14-15,18,25-27H,2,8-9H2,1H3,(H,20,23)/t12-,14-,15-,18?/m1/s1

Standard InChI Key:  FKHUTBKZORWKID-PZGKNFOESA-N

Molfile:  

     RDKit          2D

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    0.7750    0.1708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792   -2.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4958   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2792    0.8375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5000    0.5750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0167   -2.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958   -1.5167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8000   -2.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0583   -2.0042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208    0.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2083   -0.6667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9250    0.5708    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2208    1.8083    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9250   -0.2542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6000    0.1833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3167    2.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8833   -1.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042    0.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167    1.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7167    2.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375    0.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5417    1.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5375    2.9333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9542    2.2208    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
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 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 24  1  0
 28 25  2  0
 29 28  1  0
  6  5  1  0
 10  9  1  0
 11 13  2  0
 27 29  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA609377

   (3R,4S,5R)-2-[6-benzylsulfanyl-8-(ethylamino)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: 417.49

Molecular Weight (Monoisotopic): 417.1471

AlogP: 1.16

#Rotatable Bonds: 7

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: 1.50

CX LogD: 1.50

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.33

Np Likeness Score: -0.22

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