cis-2-(Hexadecyloxy)ethyl Ester of 9-{[(5S)-2-Hydroxy-2-oxido-1,4,2-dioxaphosphinan-5-yl]methyl}-2,6-diaminopurine

ID: ALA1258328

PubChem CID: 49782093

Max Phase: Preclinical

Molecular Formula: C27H49N6O5P

Molecular Weight: 568.70

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCCCCCCCCCOCCO[P@@]1(=O)CO[C@@H](Cn2cnc3c(N)nc(N)nc32)CO1

Standard InChI:  InChI=1S/C27H49N6O5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-35-17-18-37-39(34)22-36-23(20-38-39)19-33-21-30-24-25(28)31-27(29)32-26(24)33/h21,23H,2-20,22H2,1H3,(H4,28,29,31,32)/t23-,39-/m0/s1

Standard InChI Key:  SMZAMWIGTHPGIO-YMUVDJRFSA-N

Molfile:  

     RDKit          2D

 39 41  0  0  0  0  0  0  0  0999 V2000
   -5.7463    0.9559    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0242    1.3742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0270    2.2107    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7481    2.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4668    1.3737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4655    2.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2593    2.4665    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7485    1.7910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2613    1.1183    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2658    0.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5479   -0.1310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5542   -0.9631    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8404   -1.3802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1156   -0.9743    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1091   -0.1425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8274    0.2835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4015   -0.5487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1115   -1.8052    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3935   -2.2150    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3895   -3.0417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6715   -3.4515    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9610   -3.0372    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2470   -3.4464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5331   -3.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8191   -3.4422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1051   -3.0289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6089   -3.4380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3228   -3.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0368   -3.4339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7508   -3.0205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4648   -3.4297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1787   -3.0163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8927   -3.4255    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6067   -3.0121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3206   -3.4214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0345   -3.0080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7485   -3.4172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7506    3.4515    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3034    0.9578    0.0000 N   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  2  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
  9 10  1  0
 11 10  1  1
 11 12  1  0
 11 16  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 14 17  2  0
 14 18  1  1
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
  4 38  1  0
  2 39  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1258328

   9-[[(2S,5S)-2-(2-hexadecoxyethoxy)-2-oxo-1,4,2lambda5-dioxaphosphinan-5-yl]methyl]purine-2,6-diamine

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: 568.70

Molecular Weight (Monoisotopic): 568.3502

AlogP: 6.07

#Rotatable Bonds: 21

Polar Surface Area: 149.63

Molecular Species: NEUTRAL

HBA: 11

HBD: 2

#RO5 Violations: 3

HBA (Lipinski): 11

HBD (Lipinski): 4

#RO5 Violations (Lipinski): 3

CX Acidic pKa: ┄

CX Basic pKa: 6.04

CX LogP: 5.52

CX LogD: 5.50

Aromatic Rings: 2

Heavy Atoms: 39

QED Weighted: 0.13

Np Likeness Score: -0.23

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