(S)-5-(2,6-Diamino-purin-9-ylmethyl)-2-oxo-2lambda*5*-[1,4,2]dioxaphos phinan-2-ol

ID: ALA1255999

PubChem CID: 49781650

Max Phase: Preclinical

Molecular Formula: C9H13N6O4P

Molecular Weight: 300.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1nc(N)c2ncn(C[C@H]3COP(=O)(O)CO3)c2n1

Standard InChI:  InChI=1S/C9H13N6O4P/c10-7-6-8(14-9(11)13-7)15(3-12-6)1-5-2-19-20(16,17)4-18-5/h3,5H,1-2,4H2,(H,16,17)(H4,10,11,13,14)/t5-/m0/s1

Standard InChI Key:  RRXNXXPOEBRRMG-YFKPBYRVSA-N

Molfile:  

     RDKit          2D

 20 22  0  0  0  0  0  0  0  0999 V2000
    0.2774    0.1276    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9934    0.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9906    1.3719    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.2756    1.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4371    0.5420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4359    1.3698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2230    1.6256    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7082    0.9557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2250    0.2887    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2295   -0.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5176   -0.9502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5237   -1.7753    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1840   -2.1889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9028   -1.7864    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    0.9093   -0.9616    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1970   -0.5392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6068   -1.3686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7082    0.1295    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8946   -2.6024    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2732    2.6024    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
 15 16  1  0
 14 17  2  0
 15 14  1  0
  2 18  1  0
 14 19  1  0
  4 20  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA1255999

   9-[[(5S)-2-hydroxy-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: 300.21

Molecular Weight (Monoisotopic): 300.0736

AlogP: -0.45

#Rotatable Bonds: 2

Polar Surface Area: 151.40

Molecular Species: ACID

HBA: 9

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 10

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.25

CX Basic pKa: 6.04

CX LogP: -4.29

CX LogD: -3.53

Aromatic Rings: 2

Heavy Atoms: 20

QED Weighted: 0.63

Np Likeness Score: -0.22

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