Pivaloyloxymethyl Ester 9-(S)-[3-Hydroxy-2-(phosphonomethoxy)propyl]-2,6-diaminopurine

ID: ALA1258897

PubChem CID: 49781651

Max Phase: Preclinical

Molecular Formula: C15H25N6O7P

Molecular Weight: 432.37

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(C)(C)C(=O)OCOP(=O)(O)CO[C@H](CO)Cn1cnc2c(N)nc(N)nc21

Standard InChI:  InChI=1S/C15H25N6O7P/c1-15(2,3)13(23)26-7-28-29(24,25)8-27-9(5-22)4-21-6-18-10-11(16)19-14(17)20-12(10)21/h6,9,22H,4-5,7-8H2,1-3H3,(H,24,25)(H4,16,17,19,20)/t9-/m0/s1

Standard InChI Key:  KOTPMDMFHKRZJS-VIFPVBQESA-N

Molfile:  

     RDKit          2D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -0.3550   -2.7385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8344    0.9877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1138    1.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1167    2.2399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8362    2.6490    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5532    1.4048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5520    2.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3441    2.4951    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8324    1.8211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3461    1.1498    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3506    0.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6385   -0.0925    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6430   -0.9175    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9218    0.3160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9308   -1.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9382   -2.1552    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2258   -1.7385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4419   -2.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0252   -3.1083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8220   -2.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4054   -3.4781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0356   -2.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8324   -1.8844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4522   -1.5146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2449   -1.2969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2097   -0.1003    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3742    1.1237    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8386    3.4781    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6549   -2.5635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  7  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  6  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  2  0
 16  1  1  0
  1 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 22 25  1  0
 14 26  1  0
  3 27  1  0
  5 28  1  0
 16 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1258897

   [(1S)-1-[(2,6-diaminopurin-9-yl)methyl]-2-hydroxy-ethoxy]methyl-(2,2-dimethylpropanoyloxymethoxy)phosphinic acid

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: 432.37

Molecular Weight (Monoisotopic): 432.1522

AlogP: 0.07

#Rotatable Bonds: 9

Polar Surface Area: 197.93

Molecular Species: ACID

HBA: 12

HBD: 4

#RO5 Violations: 1

HBA (Lipinski): 13

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 0.84

CX Basic pKa: 6.60

CX LogP: -3.04

CX LogD: -2.29

Aromatic Rings: 2

Heavy Atoms: 29

QED Weighted: 0.24

Np Likeness Score: 0.19

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