(2R)-2-amino-4-carbamoylbutanoic acid

• ChemBase ID: 1931
• Molecular Formular: C5H10N2O3
• Molecular Mass: 146.1445
• Monoisotopic Mass: 146.06914219
• SMILES: N[C@H](CCC(=O)N)C(=O)O
• Canonical SMILES: NC(=O)CC[C@H](C(=O)O)N
• InChI: InChI=1S/C5H10N2O3/c6-3(5(9)10)1-2-4(7)8/h3H,1-2,6H2,(H2,7,8)(H,9,10)/t3-/m1/s1
• InChIKey: ZDXPYRJPNDTMRX-GSVOUGTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-4-carbamoylbutanoic acid
• IUPAC Traditional name: D-glutamine
• Synonyms: D-Glutamic acid 5-amide; D-2-Aminoglutaramic acid; D-Glutamine; D-Glutamine

Database IDs

• CAS Number: 5959-95-5
• MDL Number: MFCD00065607
• Beilstein Number: 1723796
• PubChem SID: 160965386; 24872875; 24895357; 46508385
• PubChem CID: 5961; 145815

CALCULATED PROPERTIES

JChem

• Acid pKa: 2.1471426
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -4.001106
• LogD (pH = 7.4): -4.0058823
• Log P: -4.0011334
• Molar Refractivity: 33.1099 cm^3
• Polarizability: 13.317601 Å^3
• Polar Surface Area: 106.41 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -3.32
• LOG S: -0.17
• Solubility (Water): 9.78e+01 g/l

PROPERTIES

Physical Property

• Optical Rotation: [α]20/D -34±2°, c = 5% in 5 M HCl

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98% (TLC); ≥98.5% (NT); 97%
• Salt Data: Free Base
• Ignition Residue: ≤0.05% (as SO4)
• Loss on Drying: ≤0.05% loss on drying, 20 °C (HV)
• Empirical Formula (Hill Notation): C5H10N2O3

DETAILS

MP Biomedicals - 02101801

Crystalline

DrugBank - DB02174

• Drug Groups: experimental
• Description: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from glutamic acid and ammonia. It is the principal carrier of nitrogen in the body and is an important energy source for many cells. [PubChem]

Selleck Chemicals - S1893

Research Area

• Description: Metabolic Disease

Biological Activity

• Description: D-glutamine is a D type stereoisomer of glutamine which is one of the 20 amino acids encoded by the standard genetic code.
• In Vitro: In catabolic states of injury and illness, glutamine becomes conditionally-essential (requiring intake from food or supplements). Glutamine is the most abundant naturally occurring, non-essential amino acid in the human body and one of the few amino acids that can directly cross the blood–brain barrier. ^[1] Glutamine is a key pharmaconutrient in the body's response to stress and injury. Glutamine exerts its protective effects via multiple mechanisms, including direct protection of cells and tissue from injury, attenuation inflammation, and preservation of metabolic function. ^[1]
• In Vivo: Glutamine shows the greatest benefit when administered at doses greater than 0.35 g/kg/day, with optimal benefit potentially occurring at 0.5 g/kg/day. ^[2]

References

• References: [1] Lee WJ, et al. Am J Physiol, 1998, 274(4 Pt 1), C1101-C1107.
• References: [2] Kim M, et al. World Rev Nutr Diet, 2013, 105, 90-96.

Sigma Aldrich - G9003

Other Notes
Unnatural isomer of glutamine

Sigma Aldrich - 49410

Other Notes
Unnatural isomer of glutamine

REFERENCES

• Lee WJ, et al. Am J Physiol, 1998, 274(4 Pt 1), C1101-C1107.
• Kim M, et al. World Rev Nutr Diet, 2013, 105, 90-96.