disodium [(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl phosphonato]oxy}phosphonate

• ChemBase ID: 154649
• Molecular Formular: C16H23N5Na2O16P2
• Molecular Mass: 649.304782
• Monoisotopic Mass: 649.0410415
• SMILES: c1nc2c(=O)[nH]c(nc2n1[C@H]1[C@@H]([C@@H]([C@H](O1)COP(=O)([O-])OP(=O)([O-])O[C@@H]1[C@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O)N.[Na+].[Na+]
• Canonical SMILES: OC[C@H]1O[C@H](OP(=O)(OP(=O)(OC[C@H]2O[C@H]([C@@H]([C@@H]2O)O)n2cnc3c2nc(N)[nH]c3=O)[O-])[O-])[C@H]([C@H]([C@@H]1O)O)O.[Na+].[Na+]
• InChI: InChI=1S/C16H25N5O16P2.2Na/c17-16-19-12-6(13(28)20-16)18-3-21(12)14-10(26)8(24)5(34-14)2-33-38(29,30)37-39(31,32)36-15-11(27)9(25)7(23)4(1-22)35-15;;/h3-5,7-11,14-15,22-27H,1-2H2,(H,29,30)(H,31,32)(H3,17,19,20,28);;/q;2*+1/p-2/t4-,5-,7-,8-,9+,10-,11+,14-,15-;;/m1../s1
• InChIKey: XOAGKSFNHBWACO-RAUZPKMFSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium [(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl phosphonato]oxy}phosphonate
• IUPAC Traditional name: disodium gdp-α-D-mannose(2-)
• Synonyms: GDP-D-mannose disodium salt; Guanosine 5′-diphospho-α-D-mannose disodium salt

Database IDs

• CAS Number: 148296-46-2
• MDL Number: MFCD00799981
• PubChem SID: 162248787
• PubChem CID: 11571023

CALCULATED PROPERTIES

• Acid pKa: 1.3106657
• H Acceptors: 16
• H Donor: 8
• LogD (pH = 5.5): -9.680665
• LogD (pH = 7.4): -10.0345745
• Log P: -5.495553
• Molar Refractivity: 116.2679 cm^3
• Polarizability: 47.437122 Å^3
• Polar Surface Area: 333.09 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥95.0% (HPLC)
• Empirical Formula (Hill Notation): C16H23N5Na2O16P2

DETAILS

Sigma Aldrich - 07508

Biochem/physiol Actions
Intermediate in fructose and mannose metabolism, ascorbate and aldarate metabolism1,2, amino sugar and nucleotide sugar metabolism and N-Glycan biosynthesis.