(2R)-5-oxopyrrolidine-2-carboxylic acid

• ChemBase ID: 2791
• Molecular Formular: C5H7NO3
• Molecular Mass: 129.11398
• Monoisotopic Mass: 129.04259309
• SMILES: OC(=O)[C@H]1CCC(=O)N1
• Canonical SMILES: O=C1CC[C@@H](N1)C(=O)O
• InChI: InChI=1S/C5H7NO3/c7-4-2-1-3(6-4)5(8)9/h3H,1-2H2,(H,6,7)(H,8,9)/t3-/m1/s1
• InChIKey: ODHCTXKNWHHXJC-GSVOUGTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-5-oxopyrrolidine-2-carboxylic acid
• IUPAC Traditional name: 5-oxo-D-proline
• Synonyms: Pyroglutamic Acid; D-5-Oxo-2-pyrrolidinecarboxylic acid; (R)-(+)-2-Pyrrolidone-5-carboxylic acid; (R)-5-Oxopyrrolidine-2-carboxylic acid; H-D-Pyr-OH; (R)-(+)-2-Pyrrolidinone-5-carboxylic acid; D-Pyroglutamic acid; (R)-2-Pyrrolidone-5-carboxylic acid; (R)-5-Oxo-2-pyrrolidinecarboxylic acid; (D-5-Oxo-2-pyrrolidinecarboxylic acid); D-PYROGLUTAMIC ACID; D-Pyroglutamic acid; (2R)-5-Oxopyrrolidine-2-carboxylic acid; D-5-氧代-2-吡咯烷羧酸; D-焦谷氨酸; (R)-(+)-2-吡咯烷酮-5-羧酸; D-焦谷氨酸

Database IDs

• CAS Number: 4042-36-8; 98-79-3
• EC Number: 223-735-0
• MDL Number: MFCD00066212
• Beilstein Number: 82133
• PubChem SID: 46506886; 160966239; 24866442
• PubChem CID: 439685

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.6133544
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.7721438
• LogD (pH = 7.4): -4.2279973
• Log P: -0.8896697
• Molar Refractivity: 28.0878 cm^3
• Polarizability: 11.10192 Å^3
• Polar Surface Area: 66.4 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.01
• LOG S: 0.07
• Solubility (Water): 1.51e+02 g/l

PROPERTIES

Physical Property

• Melting Point: 155-156 °C(lit.); 155-156°C; 158-160°C
• Optical Rotation: [α]22/D +10°, c = 1.5 in H2O; +10.5 (c=5 in water)

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 95%; 97%; 98%; 98+%
• Empirical Formula (Hill Notation): C5H7NO3

DETAILS

MP Biomedicals - 02156461

(D-5-Oxo-2-pyrrolidinecarboxylic acid)

DrugBank - DB03088

• Drug Groups: experimental
• Description: A cyclized derivative of L-GLUTAMIC ACID. Elevated blood levels may be associated with problems of GLUTAMINE or GLUTATHIONE metabolism. [PubChem]

Sigma Aldrich - 422614

Packaging
1, 10 g in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 422614.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

• For applications, see next entry.