sodium-2-((2R,3S,4S,5S,6S)-3,4,5-trihydroxy-6-methoxytetrahydro-2H-pyran-2-yl)vinylphosphonate

ID: ALA470777

PubChem CID: 25169390

Max Phase: Preclinical

Molecular Formula: C8H13Na2O8P

Molecular Weight: 270.17

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CO[C@H]1O[C@H](/C=C/P(=O)([O-])[O-])[C@@H](O)[C@H](O)[C@@H]1O.[Na+].[Na+]

Standard InChI:  InChI=1S/C8H15O8P.2Na/c1-15-8-7(11)6(10)5(9)4(16-8)2-3-17(12,13)14;;/h2-11H,1H3,(H2,12,13,14);;/q;2*+1/p-2/b3-2+;;/t4-,5-,6+,7+,8+;;/m1../s1

Standard InChI Key:  VFWYEPQEPXMHEC-UMWXGPIZSA-L

Molfile:  

     RDKit          2D

 19 17  0  0  0  0  0  0  0  0999 V2000
   -0.7188   -6.0312    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
    2.9784   -7.5340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2626   -7.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2626   -8.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9784   -9.1840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5467   -9.1840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5467  -10.0090    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8350   -8.7715    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1191   -9.1840    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8350   -7.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5467   -7.5340    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1192   -7.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3084   -7.5340    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7209   -8.2457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5925   -7.9465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0243   -7.1215    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8959   -6.8181    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6926   -7.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1250   -7.0313    0.0000 Na  0  0  0  0  0 15  0  0  0  0  0  0
  3  2  1  6
  3  4  1  0
  4  5  1  1
  4  6  1  0
  6  7  1  1
  6  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 10 12  1  1
  3 11  1  0
 13 14  2  0
 13 15  1  0
 13 16  1  0
 13 17  1  0
 12 15  2  0
  2 18  1  0
M  CHG  4   1   1  16  -1  17  -1  19   1
M  END

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: 270.17

Molecular Weight (Monoisotopic): 270.0505

AlogP: -1.87

#Rotatable Bonds: 3

Polar Surface Area: 136.68

Molecular Species: ACID

HBA: 6

HBD: 5

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.54

CX Basic pKa: ┄

CX LogP: -2.79

CX LogD: -5.11

Aromatic Rings: ┄

Heavy Atoms: 17

QED Weighted: 0.38

Np Likeness Score: 1.99

References

1. Jeanjean A, Gary-Bobo M, Nirdé P, Leiris S, Garcia M, Morère A..  (2008)  Synthesis of new sulfonate and phosphonate derivatives for cation-independent mannose 6-phosphate receptor targeting.,  18  (23): [PMID:18929485] [10.1016/j.bmcl.2008.09.101]

Source

Source(1):

• Scientific Literature