(2S)-2-[bis(carboxymethyl)amino]-6-(16-sulfanylhexadecanamido)hexanoic acid

• ChemBase ID: 154087
• Molecular Formular: C26H48N2O7S
• Molecular Mass: 532.73352
• Monoisotopic Mass: 532.31822289
• SMILES: C(CCCCCCCC(=O)NCCCC[C@@H](C(=O)O)N(CC(=O)O)CC(=O)O)CCCCCCCS
• Canonical SMILES: SCCCCCCCCCCCCCCCC(=O)NCCCC[C@H](N(CC(=O)O)CC(=O)O)C(=O)O
• InChI: InChI=1S/C26H48N2O7S/c29-23(17-12-10-8-6-4-2-1-3-5-7-9-11-15-19-36)27-18-14-13-16-22(26(34)35)28(20-24(30)31)21-25(32)33/h22,36H,1-21H2,(H,27,29)(H,30,31)(H,32,33)(H,34,35)/t22-/m0/s1
• InChIKey: GIASYAZZSODPPA-QFIPXVFZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[bis(carboxymethyl)amino]-6-(16-sulfanylhexadecanamido)hexanoic acid
• IUPAC Traditional name: (2S)-2-[bis(carboxymethyl)amino]-6-(16-sulfanylhexadecanamido)hexanoic acid
• Synonyms: N2,N2-Bis(carboxymethyl)-N6-(16-mercapto-1-oxohexadecyl)-L-lysine; N-[Nα,Nα-Bis(carboxymethyl)-L-lysine]-16-mercaptohexadecanamide

Database IDs

• CAS Number: 681239-94-1
• MDL Number: MFCD11114062
• PubChem SID: 162248226
• PubChem CID: 12150889

CALCULATED PROPERTIES

• Acid pKa: 2.3020391
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): 0.08501079
• LogD (pH = 7.4): -4.2955737
• Log P: 4.2255826
• Molar Refractivity: 141.889 cm^3
• Polarizability: 56.00341 Å^3
• Polar Surface Area: 144.24 Å^2
• Rotatable Bonds: 26
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97% (CHN); 97%
• Grade: for complexometry
• Empirical Formula (Hill Notation): C26H48N2O7S

DETAILS

Sigma Aldrich - 07408

Other Notes
Currently available only in Europe.
Application
N-[Nα,Nα-Bis(carboxymethyl)-L-lysine]-16-mercaptohexadecanamide is used in protein separation by linking Ni2+ and Au by coordinating with the nickel and providing a strong interaction betwenn Au-S 1.