sodium (S)-3-(hexadecyloxy)propyl(1-(2,6-diamino-9H-purin-9-yl)-3-hydroxypropan-2-yloxy)methylphosphonate

ID: ALA1258896

PubChem CID: 49782094

Max Phase: Preclinical

Molecular Formula: C28H52N6NaO6P

Molecular Weight: 600.74

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCOCCCOP(=O)([O-])CO[C@H](CO)Cn1cnc2c(N)nc(N)nc21.[Na+]

Standard InChI:  InChI=1S/C28H53N6O6P.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-17-38-18-16-19-40-41(36,37)23-39-24(21-35)20-34-22-31-25-26(29)32-28(30)33-27(25)34;/h22,24,35H,2-21,23H2,1H3,(H,36,37)(H4,29,30,32,33);/q;+1/p-1/t24-;/m0./s1

Standard InChI Key:  OBHNOGRVUHLWKD-JIDHJSLPSA-M

Molfile:  

     RDKit          2D

 42 42  0  0  0  0  0  0  0  0999 V2000
    1.9156   -9.6217    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    5.4109  -11.3872    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0205   -7.8901    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6161   -7.3061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4061   -6.4969    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6064   -6.2786    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2194   -7.6641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0137   -6.8554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1884   -6.8005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8753   -7.5774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5162   -8.1075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7176   -8.9100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5084   -9.1381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7088   -9.9398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1025   -8.5638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5033  -10.1671    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7001  -10.9660    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.2880  -10.3847    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0767  -11.5083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8970   -8.7910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3980   -5.4746    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4173   -7.5309    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.1186  -11.8050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8383  -11.3990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5497  -11.8191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2694  -11.4130    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9762  -11.8278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6956  -11.4240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4055  -11.8412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1249  -11.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8348  -11.8546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5542  -11.4509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2641  -11.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9835  -11.4642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6934  -11.8813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4128  -11.4776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1226  -11.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8422  -11.4910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5519  -11.9082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2715  -11.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9813  -11.9215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7008  -11.5178    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 15 20  1  0
  6 21  1  0
  4 22  1  0
  2 23  1  0
 23 24  1  0
  7  3  1  0
 24 25  1  0
  3  4  2  0
 25 26  1  0
  4  5  1  0
 26 27  1  0
  5  6  2  0
 27 28  1  0
  6  8  1  0
 28 29  1  0
  7  8  2  0
 29 30  1  0
  8  9  1  0
 30 31  1  0
  9 10  2  0
 31 32  1  0
 10 11  1  0
 32 33  1  0
 11  7  1  0
 33 34  1  0
 11 12  1  0
 34 35  1  0
 12 13  1  0
 35 36  1  0
 13 14  1  0
 36 37  1  0
 13 15  1  1
 37 38  1  0
 14 16  1  0
 38 39  1  0
 16 17  1  0
 39 40  1  0
 17 18  2  0
 40 41  1  0
 17  2  1  0
 41 42  1  0
 17 19  1  0
M  CHG  2   1   1  19  -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: 600.74

Molecular Weight (Monoisotopic): 600.3764

AlogP: 5.42

#Rotatable Bonds: 26

Polar Surface Area: 180.86

Molecular Species: ACID

HBA: 11

HBD: 4

#RO5 Violations: 3

HBA (Lipinski): 12

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 4

CX Acidic pKa: 1.40

CX Basic pKa: 6.60

CX LogP: 1.51

CX LogD: 2.22

Aromatic Rings: 2

Heavy Atoms: 41

QED Weighted: 0.08

Np Likeness Score: 0.07

References

1. Krecmerová M, Holý A, Andrei G, Pomeisl K, Tichý T, Brehová P, Masojídková M, Dracínský M, Pohl R, Laflamme G, Naesens L, Hui H, Cihlar T, Neyts J, De Clercq E, Balzarini J, Snoeck R..  (2010)  Synthesis of ester prodrugs of 9-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]-2,6-diaminopurine (HPMPDAP) as anti-poxvirus agents.,  53  (19): [PMID:20809641] [10.1021/jm901828c]

Source

Source(1):

• Scientific Literature