2-[4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecan-1-yl]acetic acid

• ChemBase ID: 127187
• Molecular Formular: C16H28N4O8
• Molecular Mass: 404.41552
• Monoisotopic Mass: 404.19071388
• SMILES: O=C(O)CN1CCN(CCN(CCN(CC1)CC(=O)O)CC(=O)O)CC(=O)O
• Canonical SMILES: OC(=O)CN1CCN(CCN(CCN(CC1)CC(=O)O)CC(=O)O)CC(=O)O
• InChI: InChI=1S/C16H28N4O8/c21-13(22)9-17-1-2-18(10-14(23)24)5-6-20(12-16(27)28)8-7-19(4-3-17)11-15(25)26/h1-12H2,(H,21,22)(H,23,24)(H,25,26)(H,27,28)
• InChIKey: WDLRUFUQRNWCPK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[4,7,10-tris(carboxymethyl)-1,4,7,10-tetraazacyclododecan-1-yl]acetic acid
• IUPAC Traditional name: DOTA
• Synonyms: DOTA; tetraxetan; DOTA (chelator); 1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic acid; 1,4,7,10-Tetraazacyclododecane-1,4,7,10-tetraacetic Acid Europium; Europium 1,4,7,10-Tetraazacyclododecane-N,N',N'',N'''-tetraacetic Acid; Eu-DOTA; NSC 681107-Eu; Eu-Tetraxetan; Europium DOTA; DOTA; 1,4,7,10-四氮杂环十二烷-1,4,7,10-四乙酸

Database IDs

• CAS Number: 60239-18-1
• MDL Number: MFCD00068657
• Beilstein Number: 1186987
• PubChem SID: 162221509; 24888763
• PubChem CID: 121841
• Wikipedia Title: DOTA_(chelator)

CALCULATED PROPERTIES

• Acid pKa: -0.48408458
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): -10.49421
• LogD (pH = 7.4): -13.800123
• Log P: -7.6706104
• Molar Refractivity: 96.4148 cm^3
• Polarizability: 37.894363 Å^3
• Polar Surface Area: 162.16 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: White crystalline solid

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38; R36/37/38
• Safety Statements: 26-36; S26, S36
• GHS Pictograms: GHS exclamation mark; GHS07
• GHS Signal Word: WARNING; Warning
• GHS Hazard statements: 315, 319, 335; H315-H319-H335
• GHS Precautionary statements: 261, 305+351+338; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥97.0% (CHN)
• Empirical Formula (Hill Notation): C16H28N4O8 · xH2O

DETAILS

Sigma Aldrich - 86734

Packaging
50, 250 mg in poly bottle

Toronto Research Chemicals - E939000

Bifunctional DOTA derivatives and their conjugation to peptides has become an established strategy for constructing target-specific metal containing agents including targeted MRI contrast agents and diagnostic and therapeutic radiopharmaceuticals.

REFERENCES

• Lewis, M., et al.: Bioconjug. Chem., 9, 72 (1998)
• Chappell, L., et al.: Bioorg. Med. Chem., 7, 2313 (1998)
• Prantner, A., et al.: Mol. Imaging, 2, 333 (1998)
• Allen, M., et al.: Chem. Biol., 11, 301 (1998)
• Weiner, R., et al.: BioDrugs, 19, 145 (1998)
• B