(2R)-2-{[(1S)-4-carbamimidamido-1-carboxybutyl]amino}pentanedioic acid

• ChemBase ID: 128651
• Molecular Formular: C11H20N4O6
• Molecular Mass: 304.2997
• Monoisotopic Mass: 304.13828438
• SMILES: C(C[C@@H](C(=O)O)N[C@H](CCC(=O)O)C(=O)O)CNC(=N)N
• Canonical SMILES: NC(=N)NCCC[C@@H](C(=O)O)N[C@@H](C(=O)O)CCC(=O)O
• InChI: InChI=1S/C11H20N4O6/c12-11(13)14-5-1-2-6(9(18)19)15-7(10(20)21)3-4-8(16)17/h6-7,15H,1-5H2,(H,16,17)(H,18,19)(H,20,21)(H4,12,13,14)/t6-,7+/m0/s1
• InChIKey: LMKYZBGVKHTLTN-NKWVEPMBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-{[(1S)-4-carbamimidamido-1-carboxybutyl]amino}pentanedioic acid
• IUPAC Traditional name: D-nopaline
• Synonyms: Nopaline

Database IDs

• PubChem SID: 162222958
• PubChem CID: 108012; 426
• Chemspider ID: 413
• Wikipedia Title: Nopaline

CALCULATED PROPERTIES

• Acid pKa: 2.5150635
• H Acceptors: 10
• H Donor: 7
• LogD (pH = 5.5): -7.143796
• LogD (pH = 7.4): -8.742455
• Log P: -5.8777494
• Molar Refractivity: 80.0666 cm^3
• Polarizability: 27.35534 Å^3
• Polar Surface Area: 185.83 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false