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

ID: ALA1257278

PubChem CID: 49781653

Max Phase: Preclinical

Molecular Formula: C11H16F3N6O5P

Molecular Weight: 400.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2ncn(C[C@@H](CO)OCP(=O)(O)OCC(F)(F)F)c2n1

Standard InChI:  InChI=1S/C11H16F3N6O5P/c12-11(13,14)3-25-26(22,23)5-24-6(2-21)1-20-4-17-7-8(15)18-10(16)19-9(7)20/h4,6,21H,1-3,5H2,(H,22,23)(H4,15,16,18,19)/t6-/m0/s1

Standard InChI Key:  LULPAXGGDASONW-LURJTMIESA-N

Molfile:  

     RDKit          2D

 26 27  0  0  0  0  0  0  0  0999 V2000
    0.1182   -2.4934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3612    1.2323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3593    1.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3564    2.4843    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3630    2.8933    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0800    1.6492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0788    2.4822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8707    2.7395    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3589    2.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8727    1.3944    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8772    0.5685    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1652    0.1522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1697   -0.6727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4486    0.5607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4576   -1.0889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4651   -1.9101    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.2472   -1.4936    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9149   -2.2798    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4981   -2.8631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0321   -3.3955    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4141   -3.7222    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.3589   -2.7773    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1815   -2.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2634    0.1444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3655    3.7222    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8472    1.3683    0.0000 N   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
 19 21  1  0
 19 22  1  0
 16 23  1  0
 14 24  1  0
  5 25  1  0
  3 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1257278

   [(2S)-1-(2,6-diaminopurin-9-yl)-3-hydroxypropan-2-yl]oxymethyl-(2,2,2-trifluoroethoxy)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: 400.25

Molecular Weight (Monoisotopic): 400.0872

AlogP: 0.09

#Rotatable Bonds: 8

Polar Surface Area: 171.63

Molecular Species: ACID

HBA: 10

HBD: 4

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 6

#RO5 Violations (Lipinski): 2

CX Acidic pKa: -0.13

CX Basic pKa: 6.60

CX LogP: -3.87

CX LogD: -3.10

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.45

Np Likeness Score: -0.26

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