[(1R*,3R*,4R*)-3-(6-Thio-9H-purin-9-yl)bicyclo[2.2.1]hept-1-yl]methanol

ID: ALA3353009

PubChem CID: 118719389

Max Phase: Preclinical

Molecular Formula: C13H16N4OS

Molecular Weight: 276.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@]12CC[C@H](C1)[C@H](n1cnc3c(=S)[nH]cnc31)C2

Standard InChI:  InChI=1S/C13H16N4OS/c18-5-13-2-1-8(3-13)9(4-13)17-7-16-10-11(17)14-6-15-12(10)19/h6-9,18H,1-5H2,(H,14,15,19)/t8-,9-,13-/m1/s1

Standard InChI Key:  GISDVNVWVFSCCT-JRKPZEMJSA-N

Molfile:  

     RDKit          2D

 20 23  0  0  0  0  0  0  0  0999 V2000
   22.2207   -3.5769    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.9304   -3.1674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9276   -2.3448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.2189   -1.9395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5127   -3.1679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5139   -2.3514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7377   -2.0979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.2567   -2.7578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7357   -3.4190    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.4821   -4.1958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7069   -4.4446    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7057   -5.2618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4826   -5.5155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.9638   -4.8550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0439   -5.7411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2978   -5.4076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2812   -5.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5400   -5.4314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7505   -4.6390    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   22.2152   -1.1223    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  6  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9  5  1  0
 10  9  1  1
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 10  1  0
 12 15  1  1
 15 16  1  0
 12 17  1  0
 14 18  1  0
 17 18  1  0
 14 19  1  1
  4 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA3353009

   ---

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: 276.36

Molecular Weight (Monoisotopic): 276.1045

AlogP: 2.21

#Rotatable Bonds: 2

Polar Surface Area: 66.73

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 10.89

CX Basic pKa: 1.31

CX LogP: 0.76

CX LogD: 0.76

Aromatic Rings: 2

Heavy Atoms: 19

QED Weighted: 0.83

Np Likeness Score: 0.50

References

1. Dejmek M, Šála M, Hřebabecký H, Dračínský M, Procházková E, Chalupská D, Klíma M, Plačková P, Hájek M, Andrei G, Naesens L, Leyssen P, Neyts J, Balzarini J, Boura E, Nencka R..  (2015)  Norbornane-based nucleoside and nucleotide analogues locked in North conformation.,  23  (1): [PMID:25435471] [10.1016/j.bmc.2014.11.011]

Source

Source(1):

• Scientific Literature