N6-(4-trifluoromethoxybenzyl)-adenosine

ID: ALA489467

PubChem CID: 44563534

Max Phase: Preclinical

Molecular Formula: C18H18F3N5O5

Molecular Weight: 441.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  OC[C@@H]1O[C@H](n2cnc3c(NCc4ccc(OC(F)(F)F)cc4)ncnc32)[C@@H](O)[C@H]1O

Standard InChI:  InChI=1S/C18H18F3N5O5/c19-18(20,21)31-10-3-1-9(2-4-10)5-22-15-12-16(24-7-23-15)26(8-25-12)17-14(29)13(28)11(6-27)30-17/h1-4,7-8,11,13-14,17,27-29H,5-6H2,(H,22,23,24)/t11-,13-,14-,17-/m0/s1

Standard InChI Key:  SSQVUUSLAFSAAE-MJFSBKNWSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
   -2.3288    2.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3299    1.9213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6151    1.5083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8987    1.9217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9015    2.7522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6169    3.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6153    0.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9009    0.2706    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9011   -0.5543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6161   -0.9624    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6167   -1.7865    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9018   -2.2001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1878   -0.9604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1820   -1.7824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6016   -2.0308    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0800   -1.3623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5921   -0.7009    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666   -2.8143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3865   -3.4852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8761   -4.1492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6590   -3.8887    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6530   -3.0637    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3170   -2.5740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3299   -4.3688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6268   -4.9356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1790   -5.1128    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6194    3.9863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9061    4.4010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1940    4.8194    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4899    3.6888    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3232    5.1128    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  3  4  2  0
  7  8  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 13  1  0
 18 19  1  0
  8  9  1  0
  4  5  1  0
  9 10  2  0
  2  3  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 18  1  0
 18 15  1  6
 10 11  1  0
 22 23  1  1
  5  6  2  0
 21 24  1  1
 11 12  2  0
 20 25  1  6
 12 14  1  0
 25 26  1  0
 13  9  1  0
  6 27  1  0
 13 14  2  0
 27 28  1  0
  6  1  1  0
 28 29  1  0
  1  2  2  0
 28 30  1  0
  3  7  1  0
 28 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA489467

   (2S,3R,4S,5S)-2-(hydroxymethyl)-5-[6-[[4-(trifluoromethoxy)phenyl]methylamino]purin-9-yl]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: 441.37

Molecular Weight (Monoisotopic): 441.1260

AlogP: 0.95

#Rotatable Bonds: 6

Polar Surface Area: 134.78

Molecular Species: NEUTRAL

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.45

CX Basic pKa: 3.72

CX LogP: 1.37

CX LogD: 1.37

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.44

Np Likeness Score: 0.11

References

1. Trávnícek Z, Mikulík J, Cajan M, Zboril R, Popa I..  (2008)  Novel iron complexes bearing N6-substituted adenosine derivatives: synthesis, magnetic, 57Fe Mössbauer, DFT, and in vitro cytotoxicity studies.,  16  (18): [PMID:18723360] [10.1016/j.bmc.2008.07.082]

Source

Source(1):

• Scientific Literature