sodium (2-(6-((octadec-7-enyloxy)carbonylamino)-9H-purin-9-yl)ethoxy)methylphosphonate

ID: ALA1257034

PubChem CID: 52943654

Max Phase: Preclinical

Molecular Formula: C27H44N5Na2O6P

Molecular Weight: 567.67

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCC/C=C\CCCCCCCCOC(=O)Nc1ncnc2c1ncn2CCOCP(=O)([O-])[O-].[Na+].[Na+]

Standard InChI:  InChI=1S/C27H46N5O6P.2Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-19-38-27(33)31-25-24-26(29-21-28-25)32(22-30-24)18-20-37-23-39(34,35)36;;/h9-10,21-22H,2-8,11-20,23H2,1H3,(H2,34,35,36)(H,28,29,31,33);;/q;2*+1/p-2/b10-9-;;

Standard InChI Key:  DFRYVOFEIHKTAO-XXAVUKJNSA-L

Molfile:  

     RDKit          2D

 41 40  0  0  0  0  0  0  0  0999 V2000
   -1.0661   -4.9353    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    5.9781   -2.2888    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9668   -3.1166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2471   -3.5185    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5364   -3.0960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5455   -2.2718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2674   -1.8663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2765   -1.0425    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7480   -3.3459    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2710   -2.6688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7630   -2.0075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2892   -4.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4617   -4.0241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0440   -4.7358    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2237   -4.7295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8005   -5.4434    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.5103   -5.8629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3843   -6.1555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0899   -5.0200    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9970   -0.6371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0061    0.1896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7138   -1.0464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4278   -0.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1417   -1.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8557   -0.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5697   -1.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2837   -0.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9977   -1.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7116   -0.6331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4256   -1.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1354   -0.6259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8535   -1.0320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8510   -1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1383   -2.2711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1435   -3.0961    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4307   -3.5115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4360   -4.3364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7233   -4.7518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7262   -5.5790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0108   -5.9974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8460   -6.5264    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  8 20  1  0
 20 21  2  0
 20 22  1  0
  2  3  1  0
 22 23  1  0
  3  4  2  0
 23 24  1  0
  4  5  1  0
 24 25  1  0
  5  6  2  0
 25 26  1  0
  6  7  1  0
 26 27  1  0
  7  8  1  0
 27 28  1  0
  2  7  2  0
 28 29  1  0
  5  9  1  0
 29 30  1  0
  9 10  1  0
 30 31  1  0
 10 11  2  0
 31 32  2  0
  6 11  1  0
 32 33  1  0
 12 13  1  0
 33 34  1  0
 14 15  1  0
 34 35  1  0
 16 17  2  0
 35 36  1  0
 16 18  1  0
 36 37  1  0
 16 19  1  0
 37 38  1  0
 15 16  1  0
 38 39  1  0
 13 14  1  0
 39 40  1  0
  9 12  1  0
M  CHG  4   1   1  18  -1  19  -1  41   1
M  END

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: 567.67

Molecular Weight (Monoisotopic): 567.3186

AlogP: 6.56

#Rotatable Bonds: 22

Polar Surface Area: 148.69

Molecular Species: ACID

HBA: 8

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 11

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 3

CX Acidic pKa: 1.22

CX Basic pKa: 1.93

CX LogP: 5.09

CX LogD: 3.61

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.08

Np Likeness Score: -0.17

References

1. Randhawa P, Zemlicka J, Sauerbrei A, Meier C, Hostetler KY, Beadle JR, Farasati NA, Huang Y, Bradley M..  (2008)  Anti-BK virus activity of nucleoside analogs.,  52  (4): [PMID:18285481] [10.1128/aac.01241-07]

Source

Source(1):

• Scientific Literature