(2R)-1-aminopyrrolidine-2-carboxylic acid

• ChemBase ID: 160439
• Molecular Formular: C5H10N2O2
• Molecular Mass: 130.1451
• Monoisotopic Mass: 130.07422757
• SMILES: C1CCN([C@H]1C(=O)O)N
• Canonical SMILES: NN1CCC[C@@H]1C(=O)O
• InChI: InChI=1S/C5H10N2O2/c6-7-3-1-2-4(7)5(8)9/h4H,1-3,6H2,(H,8,9)/t4-/m1/s1
• InChIKey: OUCUOMVLTQBZCY-SCSAIBSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-1-aminopyrrolidine-2-carboxylic acid
• IUPAC Traditional name: (2R)-1-aminopyrrolidine-2-carboxylic acid
• Synonyms: 1-Amino-D-proline; N-Amino-D-proline

Database IDs

• CAS Number: 10139-05-6
• PubChem SID: 162254574
• PubChem CID: 2737005

CALCULATED PROPERTIES

• Acid pKa: 4.2254643
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -2.6333618
• LogD (pH = 7.4): -3.6417117
• Log P: -2.6278133
• Molar Refractivity: 32.5484 cm^3
• Polarizability: 12.635251 Å^3
• Polar Surface Area: 66.56 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Light Yellow Crystals
• Melting Point: 155-156°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A628000

Hydrolysis of the vitamin B6 antagonist linatine, produces the toxic compound,1-amino-D-proline. The compound possesses bacteriostatic effect toward A. vinelandii. The mechanism by which aminoproline exerts its toxic effects is unknown.

REFERENCES

• Klosterman, H.J., et al.: Biochem., 6, 170 (1967)