(2R)-2-amino-5-(carbamoylamino)pentanoic acid

• ChemBase ID: 152756
• Molecular Formular: C6H13N3O3
• Molecular Mass: 175.18572
• Monoisotopic Mass: 175.09569129
• SMILES: C(C[C@H](C(=O)O)N)CNC(=O)N
• 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-/m1/s1
• InChIKey: RHGKLRLOHDJJDR-SCSAIBSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-5-(carbamoylamino)pentanoic acid
• IUPAC Traditional name: citrulline, L-
• Synonyms: (R)-2-Amino-5-ureidopentanoic acid; D-Citrulline; (R)-2-AMino-5-ureidopentanoic acid; (R)-2-氨基-5-脲戊酸; D-瓜氨酸

Database IDs

• CAS Number: 13594-51-9
• MDL Number: MFCD00216469
• Beilstein Number: 1725415
• PubChem SID: 162246899; 24856624
• PubChem CID: 637599

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

• Optical Rotation: [α]20/D -20.5±2.0°, c = 2% in 1 M HCl

Safety Information

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

Product Information

• Purity: ≥99.0%; 97%
• Empirical Formula (Hill Notation): C6H13N3O3

DETAILS

Sigma Aldrich - 27505

Packaging
500 mg in glass bottle