disodium (4R,5S,6R)-6-[(hydrogen phosphonatooxy)methyl]-2,4,5-trihydroxyoxane-2-carboxylate

• ChemBase ID: 165860
• Molecular Formular: C7H11Na2O10P
• Molecular Mass: 332.109541
• Monoisotopic Mass: 331.98852174
• SMILES: [C@@H]1([C@@H](CC(O[C@H]1COP(=O)(O)[O-])(O)C(=O)[O-])O)O.[Na+].[Na+]
• Canonical SMILES: O[C@@H]1CC(O)(O[C@H]([C@H]1O)COP(=O)(O)[O-])C(=O)[O-].[Na+].[Na+]
• InChI: InChI=1S/C7H13O10P.2Na/c8-3-1-7(12,6(10)11)17-4(5(3)9)2-16-18(13,14)15;;/h3-5,8-9,12H,1-2H2,(H,10,11)(H2,13,14,15);;/q;2*+1/p-2/t3-,4-,5+,7?;;/m1../s1
• InChIKey: HMVFXGRQDBAKQX-INIURBLLSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: disodium (4R,5S,6R)-6-[(hydrogen phosphonatooxy)methyl]-2,4,5-trihydroxyoxane-2-carboxylate
• IUPAC Traditional name: disodium (4R,5S,6R)-6-[(hydrogen phosphonatooxy)methyl]-2,4,5-trihydroxyoxane-2-carboxylate
• Synonyms: 3-Deoxy-D-arabino-2-heptulosonic Acid 7-(Dihydrogen Phosphate) Disodium; 3-Deoxy-2-keto-D-glucoheptonic Acid 7-Phosphate Disodium; DAHP Disodium; 3-Deoxy-D-arabinoheptulosonic Acid 7-Phosphate Disodium Salt

Database IDs

• PubChem SID: 162259993
• PubChem CID: 71315428

CALCULATED PROPERTIES

• Acid pKa: 1.2114459
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -7.081927
• LogD (pH = 7.4): -9.078286
• Log P: -2.1387985
• Molar Refractivity: 61.3434 cm^3
• Polarizability: 21.39857 Å^3
• Polar Surface Area: 179.64 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Yellow Solid
• Melting Point: >150°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D232050

It stands at the beginning of the enzyme-catalyzed cascade that starts with this seven-carbon carbohydrate and ends with the aromatic amino acids phenylalanine, tyrosine, and tryptophan.

REFERENCES

• Frost, J.W., et al.: Biochemistry, 23, 4465 (1984)