(S)-(3-(2,6-diamino-9H-purin-9-yl)-1-hydroxypropan-2-yloxy)methylphosphonic acid

ID: ALA261240

Cas Number: 113852-35-0

PubChem CID: 72254

Max Phase: Preclinical

Molecular Formula: C9H15N6O5P

Molecular Weight: 318.23

Molecule Type: Small molecule

Names and Identifiers

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

Standard InChI:  InChI=1S/C9H15N6O5P/c10-7-6-8(14-9(11)13-7)15(3-12-6)1-5(2-16)20-4-21(17,18)19/h3,5,16H,1-2,4H2,(H2,17,18,19)(H4,10,11,13,14)/t5-/m0/s1

Standard InChI Key:  XGTJCNSZEASLLL-YFKPBYRVSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
   -0.7954   -2.1999    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2803   -1.5324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7954   -0.8650    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0108   -1.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7037   -0.7074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4182   -1.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4182   -1.9449    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7037   -2.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0108   -1.9449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7037   -3.1824    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1326   -0.7074    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0503   -0.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4983    0.5327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3087    0.3612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7532    1.3174    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2012    1.9305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4562    2.7151    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7111    3.4997    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3285    2.9700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2408    2.4601    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8607    0.9743    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  1  9  1  0
  4  9  1  0
  8 10  1  0
  6 11  1  0
 12 13  1  0
 13 14  1  0
 15 16  1  0
 17 18  2  0
 17 19  1  0
 17 20  1  0
 16 17  1  0
 13 15  1  6
 14 21  1  0
  3 12  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA261240

   9-(3-Hydroxy-2-phosphonomethoxypropyl)-2,6-diaminopurine

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: 318.23

Molecular Weight (Monoisotopic): 318.0842

AlogP: -1.50

#Rotatable Bonds: 6

Polar Surface Area: 182.63

Molecular Species: ACID

HBA: 9

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 11

HBD (Lipinski): 7

#RO5 Violations (Lipinski): 2

CX Acidic pKa: 1.35

CX Basic pKa: 6.56

CX LogP: -5.30

CX LogD: -4.72

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.39

Np Likeness Score: 0.01

References

1. Lebeau I, Andrei G, Krecmerová M, De Clercq E, Holy A, Snoeck R..  (2007)  Inhibitory activities of three classes of acyclic nucleoside phosphonates against murine polyomavirus and primate simian virus 40 strains.,  51  (6): [PMID:17420214] [10.1128/aac.01422-06]

2. Duraffour S, Snoeck R, Krecmerová M, van Den Oord J, De Vos R, Holy A, Crance JM, Garin D, De Clercq E, Andrei G..  (2007)  Activities of several classes of acyclic nucleoside phosphonates against camelpox virus replication in different cell culture models.,  51  (12): [PMID:17893157] [10.1128/aac.00838-07]

3. 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]

4. Cheviet T, Lefebvre-Tournier I, Wein S, Peyrottes S..  (2019)  Plasmodium Purine Metabolism and Its Inhibition by Nucleoside and Nucleotide Analogues.,  62  (18): [PMID:30964283] [10.1021/acs.jmedchem.9b00182]

Source

Source(1):

• Scientific Literature