(2R)-2,3-bis(phosphonooxy)propanoic acid sodium

• ChemBase ID: 155254
• Molecular Formular: C3H8NaO10P2
• Molecular Mass: 289.026912
• Monoisotopic Mass: 288.949039
• SMILES: C([C@H](C(=O)O)OP(=O)(O)O)OP(=O)(O)O.[Na]
• Canonical SMILES: OC(=O)[C@H](OP(=O)(O)O)COP(=O)(O)O.[Na]
• InChI: InChI=1S/C3H8O10P2.Na/c4-3(5)2(13-15(9,10)11)1-12-14(6,7)8;/h2H,1H2,(H,4,5)(H2,6,7,8)(H2,9,10,11);/t2-;/m1./s1
• InChIKey: VYCPLSQDXLSXBN-HSHFZTNMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2,3-bis(phosphonooxy)propanoic acid sodium
• IUPAC Traditional name: diphosphoglycerate sodium
• Synonyms: 2,3-DPG; D-Glycerate 2,3-diphosphate sodium salt; 2,3-Diphospho-D-glyceric acid pentasodium salt; D-甘油酸-2,3-二磷酸 钠盐; 2,3-二磷酸-D-甘油酸 五钠盐

Database IDs

• CAS Number: 102783-53-9
• MDL Number: MFCD00070074
• PubChem SID: 24893967; 162249392
• PubChem CID: 16219258

CALCULATED PROPERTIES

• Acid pKa: 0.4809322
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -8.739837
• LogD (pH = 7.4): -12.565099
• Log P: -1.7658715
• Molar Refractivity: 42.1293 cm^3
• Polarizability: 17.66306 Å^3
• Polar Surface Area: 170.82 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Impurities: 3-phosphoglyceric acid, essentially free
• Linear Formula: C3H3O10P2Na5

DETAILS

Sigma Aldrich - D5764

Biochem/physiol Actions
Metabolite of glycolysis within human erythrocytes produced by 2,3-diphosphoglycerate mutase in an alternative to the glycolytic pathway. Binds to hemaglobin to reduce oxygenation.
Application
D-Glycerate 2,3-diphosphate, cofactor of both phosphoglyceric acid mutase and hemoglobin, may be used as a reference compound in analysis of blood cell (erythrocyte) glycolysic cycle metabolites.