(2S)-2-amino-5-(carbamoylamino)(3,3,4,4,5,5-2H6)pentanoic acid

• ChemBase ID: 164590
• Molecular Formular: C6H13N3O3
• Molecular Mass: 175.18572
• Monoisotopic Mass: 175.09569129
• SMILES: NC(=O)NCCC[C@H](N)C(=O)O
• Canonical SMILES: NC(=O)NCCC[C@@H](C(=O)O)N
• InChI: InChI=1S/C6H13N3O3/c7-4(5(10)11)2-1-3-9-6(8)12/h4H,1-3,7H2,(H,10,11)(H3,8,9,12)/t4-/m0/s1
• InChIKey: RHGKLRLOHDJJDR-BYPYZUCNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-5-(carbamoylamino)(3,3,4,4,5,5-^2H₆)pentanoic acid
• IUPAC Traditional name: (2S)-2-amino-5-(carbamoylamino)(3,3,4,4,5,5-^2H₆)pentanoic acid
• Synonyms: N5-(Aminocarbonyl)-L-ornithine-d6; Citrulline-d6; N5-Carbamoyl-L-ornithine-d6; NSC 27425-d6; Nδ-Carbamylornithine-d6; α-Amino-δ-ureidovaleric Acid-d6; δ-Ureidonorvaline-d6; L-Citrulline-d6

Database IDs

• PubChem SID: 162258725
• PubChem CID: 46781035

CALCULATED PROPERTIES

• Acid pKa: 2.2682476
• H Acceptors: 4
• H Donor: 4
• LogD (pH = 5.5): -3.9319353
• LogD (pH = 7.4): -3.9377463
• Log P: -3.9319577
• Molar Refractivity: 41.329 cm^3
• Polarizability: 16.298895 Å^3
• Polar Surface Area: 118.44 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 202-205°C (dec.)

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C535702

Labelled L-Citrulline. An amino acid, first isolated from the juice of watermelon, Citrullus vulgaris Schrad., Cucurbitaceae. Used in the treatment of asthenia.

REFERENCES

• Rajantie, J., et al.: J. Pediatr., 97, 927 (1938)
• Carpenter, T.O., et al.: N. Engl. J. Med., 312, 290 (1938)
• Kurtz, et al.: J. Biol. Chem., 122, 477 (1938)