(2S)-2-[(2S,5S,8S,11S)-4,10-bis[(1S)-1-carboxyethyl]-2,5,8,11-tetramethyl-7-[(1S)-1-{[2-(pyridin-2-yldisulfanyl)ethyl]carbamoyl}ethyl]-1,4,7,10-tetraazacyclododecan-1-yl]propanoic acid

• ChemBase ID: 174848
• Molecular Formular: C31H52N6O7S2
• Molecular Mass: 684.91058
• Monoisotopic Mass: 684.33389003
• SMILES: N1(C[C@@H](N(C[C@@H](N(C[C@@H](N(C[C@@H]1C)[C@H](C(=O)NCCSSc1ccccn1)C)C)[C@@H](C)C(=O)O)C)[C@@H](C)C(=O)O)C)[C@@H](C)C(=O)O
• Canonical SMILES: C[C@H]1CN([C@@H](C)CN([C@H](CN([C@H](CN1[C@H](C(=O)NCCSSc1ccccn1)C)C)[C@H](C(=O)O)C)C)[C@H](C(=O)O)C)[C@H](C(=O)O)C
• InChI: InChI=1S/C31H52N6O7S2/c1-19-16-35(24(6)29(39)40)21(3)18-37(26(8)31(43)44)22(4)17-36(25(7)30(41)42)20(2)15-34(19)23(5)28(38)33-13-14-45-46-27-11-9-10-12-32-27/h9-12,19-26H,13-18H2,1-8H3,(H,33,38)(H,39,40)(H,41,42)(H,43,44)/t19-,20-,21-,22-,23-,24-,25-,26-/m0/s1
• InChIKey: BVEXZTXAUQXVNC-CAQMSIDYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S,5S,8S,11S)-4,10-bis[(1S)-1-carboxyethyl]-2,5,8,11-tetramethyl-7-[(1S)-1-{[2-(pyridin-2-yldisulfanyl)ethyl]carbamoyl}ethyl]-1,4,7,10-tetraazacyclododecan-1-yl]propanoic acid
• IUPAC Traditional name: (2S)-2-[(2S,5S,8S,11S)-4,10-bis[(1S)-1-carboxyethyl]-2,5,8,11-tetramethyl-7-[(1S)-1-{[2-(pyridin-2-yldisulfanyl)ethyl]carbamoyl}ethyl]-1,4,7,10-tetraazacyclododecan-1-yl]propanoic acid
• Synonyms: (α1S,α4S,α7S,2S,5S,8S,11S)-α1,α4,α7,2,5,8,11-Heptamethyl-10-[(1S)-1-methyl-2-oxo-2-[[2-(2-pyridinyldithio)ethyl]amino]ethyl]-1,4,7,10-tetraazacyclododecane-1,4,7-triacetic Acid; (S)-M8-SPy

Database IDs

• CAS Number: 1192364-56-9
• PubChem SID: 164230758
• PubChem CID: 71750862

CALCULATED PROPERTIES

• Acid pKa: 1.14648
• H Acceptors: 12
• H Donor: 4
• LogD (pH = 5.5): -3.5192215
• LogD (pH = 7.4): -5.2270336
• Log P: -2.6133168
• Molar Refractivity: 179.8584 cm^3
• Polarizability: 71.65329 Å^3
• Polar Surface Area: 166.85 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M755300

A new lanthanide chelating tag (M8) for paramagnetic labeling of biomols. is presented, which is based on an eight-fold, stereoselectively methyl-substituted DOTA that can be covalently linked to the host molecule by a single disulfide bond. The steric ov

REFERENCES

• Ebright, Y., et al.: Biochemistry, 31, 10664 (1992)
• Gaponenko, V., et al.: Biochemistry, 2000, 39, 15217 (1992)
• Su, X., et al.: ChemBioChem., 7, 1599 (1992)