potassium 2-(hydrogen phosphonatooxy)prop-2-enoic acid

• ChemBase ID: 133861
• Molecular Formular: C3H4KO6P
• Molecular Mass: 206.132321
• Monoisotopic Mass: 205.93825616
• SMILES: C=C(C(=O)O)OP(=O)(O)[O-].[K+]
• Canonical SMILES: OC(=O)C(=C)OP(=O)(O)[O-].[K+]
• InChI: InChI=1S/C3H5O6P.K/c1-2(3(4)5)9-10(6,7)8;/h1H2,(H,4,5)(H2,6,7,8);/q;+1/p-1
• InChIKey: SOSDSEAIODNVPX-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: potassium 2-(hydrogen phosphonatooxy)prop-2-enoic acid
• IUPAC Traditional name: potassium 2-(hydrogen phosphonatooxy)prop-2-enoic acid
• Synonyms: PEP monopotassium salt; Phospho(enol)pyruvate potassium salt; mono-Potassium phosphoenolpyruvate; Monopotassium phosphoenolpyruvate; Phosphoenolpyruvic acid monopotassium salt; PEP-K; Phospho(enol)pyruvic acid monopotassium salt; PEP 单钾盐; 磷酸烯醇丙酮酸盐 钾盐; 磷酸烯醇丙酮酸酯一钾; 2-(膦酰氧基)-2-丙烯酸 单钾盐; 磷酸烯醇丙酮酸单钾盐; 磷烯醇丙酮酸 单钾盐

Database IDs

• CAS Number: 4265-07-0
• EC Number: 224-247-0
• MDL Number: MFCD00044476
• Beilstein Number: 4603446
• PubChem SID: 24888496; 162228138; 24898822
• PubChem CID: 23678879

CALCULATED PROPERTIES

• Acid pKa: 0.7594135
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -5.068693
• LogD (pH = 7.4): -7.721958
• Log P: -0.63957554
• Molar Refractivity: 29.01 cm^3
• Polarizability: 11.825219 Å^3
• Polar Surface Area: 106.89 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 175 °C (dec.)(lit.); ca 170°C dec.

Safety Information

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

Product Information

• Purity: ≥97% (enzymatic); 99%
• Salt Data: K+
• Linear Formula: KOP(O)(OH)OC(=CH2)CO2H
• Classification: Rare Derivatives of Natural Compounds

DETAILS

Sigma Aldrich - P7127

Biochem/physiol Actions
Phospho(enol)pyruvic acid (PEP) is involved in glycolysis and gluconeogeneis. In glycolysis, PEP is metabolized by Pyruvate Kinase to yield pyruvate. In plants, PEP is involved in the formation of aromatic amino acids as well as in the carbon fixation pathway.

Sigma Aldrich - 860077

Application
Substrate for many kinase reactions.
Packaging
1 g in glass bottle
250 mg in glass bottle

REFERENCES

• Used for regeneration of ATP from ADP in enzyme-catalyzed syntheses: J. Org. Chem., 47, 3765 (1982); 50,1076 (1985); J. Am. Chem. Soc., 107, 7019 (1985).