1-(phosphonooxy)cyclopropane-1-carboxylic acid; bis(cyclohexanamine)

• ChemBase ID: 170402
• Molecular Formular: C16H33N2O6P
• Molecular Mass: 380.416781
• Monoisotopic Mass: 380.20762342
• SMILES: C1(CC1)(OP(=O)(O)O)C(=O)O.C1CCC(CC1)N.C1CCC(CC1)N
• Canonical SMILES: OC(=O)C1(CC1)OP(=O)(O)O.NC1CCCCC1.NC1CCCCC1
• InChI: InChI=1S/2C6H13N.C4H7O6P/c2*7-6-4-2-1-3-5-6;5-3(6)4(1-2-4)10-11(7,8)9/h2*6H,1-5,7H2;1-2H2,(H,5,6)(H2,7,8,9)
• InChIKey: YQFYDXKZAMOLHZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-(phosphonooxy)cyclopropane-1-carboxylic acid; bis(cyclohexanamine)
• IUPAC Traditional name: 1-(phosphonooxy)cyclopropane-1-carboxylic acid; bis(cyclohexylamine)
• Synonyms: 1-(Phosphonooxy)cyclopropanecarboxylic Acid with Cyclohexanamine; 1-Hydroxycyclopropanecarboxylic Acid Phosphate, Biscyclohexylamine Salt

Database IDs

• CAS Number: 94017-79-5
• PubChem SID: 164226312
• PubChem CID: 71748960

CALCULATED PROPERTIES

• Acid pKa: 1.1075586
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -4.8340297
• LogD (pH = 7.4): -7.3036323
• Log P: -0.4704481
• Molar Refractivity: 32.4698 cm^3
• Polarizability: 13.301378 Å^3
• Polar Surface Area: 104.06 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Crystalline Solid
• Melting Point: 173-175°C

DETAILS

Toronto Research Chemicals - H927500

A potent reversible inhibitor of enzymes utilizing phosphoenolpyruvate (PEP), such as phosphoenolpyruvate carboxylase which catalyzes the carboxylation of PEP to give oxaloacetate.

REFERENCES

• O’Leary, M.H., et al.: Biochem. Biophys. Res. Commun., 100, 1320 (1981)