(2S,4S)-4-hydroxy(3,3,4,5,5-2H5)pyrrolidine-2-carboxylic acid

• ChemBase ID: 170993
• 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-/m0/s1
• InChIKey: PMMYEEVYMWASQN-IMJSIDKUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S)-4-hydroxy(3,3,4,5,5-^2H₅)pyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2S,4S)-4-hydroxy(3,3,4,5,5-^2H₅)pyrrolidine-2-carboxylic acid
• Synonyms: (4S)-4-Hydroxy-L-proline-d5; (2S,4S)-4-Hydroxyproline-d5; (S)-Allo-hydroxyproline-d5; (2S,4S)-4-Hydroxypyrrolidine-2-carboxylic Acid-d5; L-Allohydroxyproline-d5; cis-4-Hydroxyproline-d5; cis-Hydroxyproline-d5; cis-4-Hydroxy-L-proline-d5(Mixture of Diastereomers)

Database IDs

• PubChem SID: 164226903
• PubChem CID: 71749211

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 - H952377

Labelled Hydroxyprolines are valuable chiral building blocks for organic synthesis of pharmaceuticals. Several microorganisms producing proline trans-4- and cis-3-hydroxylase were discovered and these enzymes were applied to the industrial production of t

REFERENCES

• Lawrence, C., et al.: Biochem. J., 313, 185 (1996)
• Mori, H., et al.: J. Bacteriol., 179, 5677 (1996)
• Clifton, I., et al.: Eur. J. Biochem., 268, 6625 (1996)