N-(2-{2-[2-(2-{11-[({2-[2-(2-octadecanamidoethoxy)ethoxy]ethyl}carbamoyl)methyl]-3,13,16-trioxo-2,14,15-trioxa-5,8,11-triaza-1-gadolinabicyclo[6.6.3]heptadecan-5-yl}acetamido)ethoxy]ethoxy}ethyl)octadecanamide

• ChemBase ID: 131144
• Molecular Formular: C62H116GdN7O14
• Molecular Mass: 1340.87294
• Monoisotopic Mass: 1340.78212943
• SMILES: CCCCCCCCCCCCCCCCCC(=O)NCCOCCOCCNC(=O)CN1CCN2CCN(CC(=O)O[Gd](OC(=O)C2)OC(=O)C1)CC(=O)NCCOCCOCCNC(=O)CCCCCCCCCCCCCCCCC
• Canonical SMILES: CCCCCCCCCCCCCCCCCC(=O)NCCOCCOCCNC(=O)CN1CCN2CCN(CC(=O)NCCOCCOCCNC(=O)CCCCCCCCCCCCCCCCC)CC(=O)O[Gd](OC(=O)C1)OC(=O)C2
• InChI: InChI=1S/C62H119N7O14.Gd/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-56(70)63-35-43-80-47-49-82-45-37-65-58(72)51-68(54-61(76)77)41-39-67(53-60(74)75)40-42-69(55-62(78)79)52-59(73)66-38-46-83-50-48-81-44-36-64-57(71)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2;/h3-55H2,1-2H3,(H,63,70)(H,64,71)(H,65,72)(H,66,73)(H,74,75)(H,76,77)(H,78,79);/q;+3/p-3
• InChIKey: YCQABDWULYMBBW-UHFFFAOYSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(2-{2-[2-(2-{11-[({2-[2-(2-octadecanamidoethoxy)ethoxy]ethyl}carbamoyl)methyl]-3,13,16-trioxo-2,14,15-trioxa-5,8,11-triaza-1-gadolinabicyclo[6.6.3]heptadecan-5-yl}acetamido)ethoxy]ethoxy}ethyl)octadecanamide
• IUPAC Traditional name: N-(2-{2-[2-(2-{11-[({2-[2-(2-octadecanamidoethoxy)ethoxy]ethyl}carbamoyl)methyl]-3,13,16-trioxo-2,14,15-trioxa-5,8,11-triaza-1-gadolinabicyclo[6.6.3]heptadecan-5-yl}acetamido)ethoxy]ethoxy}ethyl)octadecanamide
• Synonyms: Diethylenetriaminepentaacetic acid α,ω-bis(8-stearoylamido-3,6-dioxaoctylamide) gadolinium salt

Database IDs

• MDL Number: MFCD01632609
• PubChem SID: 162225422
• PubChem CID: 71308392

CALCULATED PROPERTIES

• Acid pKa: 14.335376
• H Acceptors: 14
• H Donor: 4
• LogD (pH = 5.5): 7.29862
• LogD (pH = 7.4): 7.4764943
• Log P: 7.4793
• Molar Refractivity: 323.3493 cm^3
• Polarizability: 134.06218 Å^3
• Polar Surface Area: 241.94 Å^2
• Rotatable Bonds: 54
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ~99% (TLC)

DETAILS

Sigma Aldrich - D0559

Application
DTPA-based chelator lipid useful as a liposome component. The paramagnetic gadolinium ligand makes the liposome traceable by magnetic resonance imaging (MRI).
Legal Information
U.S. Patent No. 5,512,294.