sodium (2-(6-octadec-9-enamido-9H-purin-9-yl)ethoxy)methylphosphonate

ID: ALA1257009

PubChem CID: 52949749

Max Phase: Preclinical

Molecular Formula: C26H42N5Na2O5P

Molecular Weight: 537.64

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C26H44N5O5P.2Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-23(32)30-25-24-26(28-20-27-25)31(21-29-24)18-19-36-22-37(33,34)35;;/h9-10,20-21H,2-8,11-19,22H2,1H3,(H2,33,34,35)(H,27,28,30,32);;/q;2*+1/p-2/b10-9-;;

Standard InChI Key:  VVJBYSBFIOOZLF-XXAVUKJNSA-L

Molfile:  

     RDKit          2D

 39 38  0  0  0  0  0  0  0  0999 V2000
   -0.5373   -3.5623    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    5.6325   -1.6946    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6213   -2.5224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9016   -2.9242    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1910   -2.5019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2001   -1.6776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9220   -1.2721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9310   -0.4483    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.4020   -2.7523    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9255   -2.0747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4176   -1.4133    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9643   -3.4517    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1370   -3.4685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7410   -4.1926    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9136   -4.2094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5147   -4.9363    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    1.2416   -5.3354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1186   -5.6604    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2094   -4.5344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6515   -0.0429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6606    0.7837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3683   -0.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0822   -0.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7962   -0.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5102   -0.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2242   -0.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9382   -0.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6521   -0.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3661   -0.0390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0767   -0.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0794   -1.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3654   -1.6877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3680   -2.5127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6540   -2.9259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6567   -3.7509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9427   -4.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9453   -4.9890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2313   -5.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6265   -6.5272    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  9 12  1  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  2  0
  9 10  1  0
 30 31  1  0
 10 11  2  0
 31 32  1  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
 13 14  1  0
M  CHG  4   1   1  18  -1  19  -1  39   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: 537.64

Molecular Weight (Monoisotopic): 537.3080

AlogP: 5.95

#Rotatable Bonds: 21

Polar Surface Area: 139.46

Molecular Species: ACID

HBA: 7

HBD: 3

#RO5 Violations: 2

HBA (Lipinski): 10

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.29

CX Basic pKa: 2.22

CX LogP: 4.12

CX LogD: 2.81

Aromatic Rings: 2

Heavy Atoms: 37

QED Weighted: 0.10

Np Likeness Score: -0.23

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