(2S,4R)-4-hydroxy(2,5,5-2H3)pyrrolidine-2-carboxylic acid

• ChemBase ID: 170994
• Molecular Formular: C5H9NO3
• Molecular Mass: 131.12986
• Monoisotopic Mass: 131.05824315
• SMILES: C1[C@@H](C[C@H](N1)C(=O)O)O
• Canonical SMILES: O[C@H]1CN[C@@H](C1)C(=O)O
• InChI: InChI=1S/C5H9NO3/c7-3-1-4(5(8)9)6-2-3/h3-4,6-7H,1-2H2,(H,8,9)/t3-,4+/m1/s1
• InChIKey: PMMYEEVYMWASQN-DMTCNVIQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4R)-4-hydroxy(2,5,5-^2H₃)pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2S,4R)-4-hydroxy(2,5,5-^2H₃)pyrrolidine-2-carboxylic acid
• Synonyms: (R)-4-Hydroxy-(S)-proline-d3; 4(R)-Hydroxy-2(S)-pyrrolidinecarboxylic Acid-d3; 4-trans-Hydroxy-L-proline-d3; L-Hypro-d3; NSC 46704-d3; trans-4-Hydroxy-L-proline-d3; trans-4-Hydroxy-L-proline-2,5,5-d3; (-)-4-Hydroxy-2-pyrrolidinecarboxylic Acid-d3; (2S,4R)-(-)-4-Hydroxyproline-d3

Database IDs

• PubChem SID: 164226904
• PubChem CID: 71749212

CALCULATED PROPERTIES

• Acid pKa: 1.641382
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -3.7163465
• LogD (pH = 7.4): -3.7165344
• Log P: -3.7163188
• Molar Refractivity: 29.3822 cm^3
• Polarizability: 11.9828205 Å^3
• Polar Surface Area: 69.56 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H952378

A labelled trans-4-Hydroxy-L-proline. A natural constituent of animal structural proteins such as collagen and elastin. Several microorganisms producing proline trans-4- and cis-3-hydroxylase were discovered and these enzymes were applied to the industria

REFERENCES

• Langmaier, F. et al.: Int. J. Cosm. Sci., 24, 273 (2002)
• Lawrence, C., et al.: Biochem. J., 313, 185 (2002)
• Mori, H., et al.: J. Bacteriol.; 179, 5677 (2002)
• Clifton, I., et al.: Eur. J. Biochem., 268, 6625 (2002)