(2S)-2-amino-5-(3,3-dimethylcarbamimidamido)pentanoic acid

• ChemBase ID: 125970
• Molecular Formular: C8H18N4O2
• Molecular Mass: 202.25412
• Monoisotopic Mass: 202.14297584
• SMILES: CN(C)C(=N)NCCC[C@H](N)C(=O)O
• Canonical SMILES: OC(=O)[C@H](CCCNC(=N)N(C)C)N
• InChI: InChI=1S/C8H18N4O2/c1-12(2)8(10)11-5-3-4-6(9)7(13)14/h6H,3-5,9H2,1-2H3,(H2,10,11)(H,13,14)/t6-/m0/s1
• InChIKey: YDGMGEXADBMOMJ-LURJTMIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-5-(3,3-dimethylcarbamimidamido)pentanoic acid
• IUPAC Traditional name: dimethyl-L-arginine
• Synonyms: 2-Amino-5-[(amino-dimethylaminomethylene)amino]pentanoic acid; Asymmetric dimethylarginine

Database IDs

• CAS Number: 30315-93-6
• Beilstein Number: 2261521 S
• PubChem SID: 162220313
• PubChem CID: 123831; 501
• CHEBI ID: 17929
• CHEMBL: 457530
• Chemspider ID: 487
• DrugBank ID: DB01686
• KEGG ID: C03626
• MeSH Name: N,N-dimethylarginine
• Wikipedia Title: Asymmetric_dimethylarginine

CALCULATED PROPERTIES

• Acid pKa: 2.5396655
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -5.525824
• LogD (pH = 7.4): -4.299206
• Log P: -2.6065567
• Molar Refractivity: 63.9924 cm^3
• Polarizability: 20.554567 Å^3
• Polar Surface Area: 102.44 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Partition Coefficient: -0.716
• pKa: 2.497
• pKb: 11.500