trisodium (3R,4S,5R)-4,5-dihydroxy-3-(phosphonatooxy)cyclohex-1-ene-1-carboxylate

• ChemBase ID: 177759
• Molecular Formular: C7H8Na3O8P
• Molecular Mass: 320.076691
• Monoisotopic Mass: 319.96498669
• SMILES: [C@@H]1([C@H]([C@@H](CC(=C1)C(=O)[O-])O)O)OP(=O)([O-])[O-].[Na+].[Na+].[Na+]
• Canonical SMILES: O[C@H]1[C@H](O)CC(=C[C@H]1OP(=O)([O-])[O-])C(=O)[O-].[Na+].[Na+].[Na+]
• InChI: InChI=1S/C7H11O8P.3Na/c8-4-1-3(7(10)11)2-5(6(4)9)15-16(12,13)14;;;/h2,4-6,8-9H,1H2,(H,10,11)(H2,12,13,14);;;/q;3*+1/p-3/t4-,5-,6+;;;/m1.../s1
• InChIKey: SQZCNOWSDNBSGQ-PFYBVYJXSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trisodium (3R,4S,5R)-4,5-dihydroxy-3-(phosphonatooxy)cyclohex-1-ene-1-carboxylate
• IUPAC Traditional name: trisodium 3-phosphoshikimate
• Synonyms: (3R,4S,5R)-4,5-Dihydroxy-3-(phosphonooxy)-1-cyclohexene-1-carboxylic Acid Sodium Salt; [3R-(3α,4α,5β)]-4,5-Dihydroxy-3-(phosphonooxy)-1-cyclohexene-1-carboxylic Acid Trisodium Salt; S-3-P Trisodium; Shikimate-3-phosphate Trisodium Salt 90%

Database IDs

• CAS Number: 143393-03-7
• PubChem SID: 164233669
• PubChem CID: 11771565

CALCULATED PROPERTIES

• Acid pKa: 1.3157644
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -5.590323
• LogD (pH = 7.4): -8.215488
• Log P: -1.7636402
• Molar Refractivity: 58.4269 cm^3
• Polarizability: 19.479197 Å^3
• Polar Surface Area: 153.01 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White to Off-White Solid
• Melting Point: >135°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - S357026

S-3-p is the substrate for 5-Enolpyruvoyl-shikimate 3-phosphate synthase (EPSPS) which is the target for the broad-spectrum herbicide N-(phosphonomethyl)glycine(glyphosate).

REFERENCES

• Chahoua, L., et al.: J. Org. Chem., 57, 5798 (1992)