(2R)-2-amino-5-carbamimidamidopentanoic acid hydrochloride

• ChemBase ID: 102232
• Molecular Formular: C6H15ClN4O2
• Molecular Mass: 210.6619
• Monoisotopic Mass: 210.08835342
• SMILES: Cl.N[C@H](CCCNC(=N)N)C(=O)O
• Canonical SMILES: NC(=N)NCCC[C@H](C(=O)O)N.Cl
• InChI: InChI=1S/C6H14N4O2.ClH/c7-4(5(11)12)2-1-3-10-6(8)9;/h4H,1-3,7H2,(H,11,12)(H4,8,9,10);1H/t4-;/m1./s1
• InChIKey: KWTQSFXGGICVPE-PGMHMLKASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-amino-5-carbamimidamidopentanoic acid hydrochloride
• IUPAC Traditional name: D-arginine hydrochloride
• Synonyms: D-ARGININE HCl; D-Arginine monohydrochloride; D-ARGININE HYDROCHLORIDE; (R)-(-)-Arginine hydrochloride; D-Arginine hydrochloride; D-精氨酸盐酸盐; D-精氨酸 单盐酸盐; (R)-(-)-精氨酸 盐酸盐; D-精氨酸 盐酸盐

Database IDs

• CAS Number: 627-75-8
• EC Number: 211-010-1
• MDL Number: MFCD00012620
• Beilstein Number: 5773432
• PubChem SID: 24846990; 24891136; 162090528
• PubChem CID: 12326

CALCULATED PROPERTIES

• Acid pKa: 2.4118392
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -6.1142516
• LogD (pH = 7.4): -5.121845
• Log P: -3.1615653
• Molar Refractivity: 53.9231 cm^3
• Polarizability: 16.904032 Å^3
• Polar Surface Area: 125.22 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 216-218 °C(lit.); 216-218°C; 216-218°C
• Optical Rotation: [α]20/D -21.8±0.5°, c = 5% in 5 M HCl; [α]23/D -21°, c = 2 in 6 M HCl

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• RTECS: CF1995000
• German water hazard class: 3
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98% (TLC); ≥99.0%; 98%; 99%
• Linear Formula: HN=C(NH2)NH(CH2)3CH(NH2)COOH · HCl
• Empirical Formula (Hill Notation): C6H14N4O2 · HCl

DETAILS

MP Biomedicals - 02100730

Hydrochloride

MP Biomedicals - 05211594

MP Biomedicals Rare Chemical collection

Sigma Aldrich - A6757

Application
D-arginine attenuates increased arginase expression, oxidative stress, endothelial dysfunction, and advanced glycation endproducts formation induced by methylgloxyl and high glucose. This attenuation by D-arginine is thought to occur through an endothelial NOS independent mechanism.