4-({5-[bis(carboxymethyl)amino]-5-carboxypentyl}carbamoyl)-2-(2,7-dichloro-6-hydroxy-3-oxo-8a,10a-dihydro-3H-xanthen-9-yl)benzoic acid

• ChemBase ID: 162237
• Molecular Formular: C31H28Cl2N2O12
• Molecular Mass: 691.46622
• Monoisotopic Mass: 690.10192971
• SMILES: C1(=O)C(=CC2=C(C3C(OC2=C1)C=C(C(=C3)Cl)O)c1cc(ccc1C(=O)O)C(=O)NCCCCC(N(CC(=O)O)CC(=O)O)C(=O)O)Cl
• Canonical SMILES: OC(=O)CN(C(C(=O)O)CCCCNC(=O)c1ccc(c(c1)C1=C2C=C(Cl)C(=O)C=C2OC2C1C=C(Cl)C(=C2)O)C(=O)O)CC(=O)O
• InChI: InChI=1S/C31H28Cl2N2O12/c32-19-8-17-24(10-22(19)36)47-25-11-23(37)20(33)9-18(25)28(17)16-7-14(4-5-15(16)30(43)44)29(42)34-6-2-1-3-21(31(45)46)35(12-26(38)39)13-27(40)41/h4-5,7-11,17,21,24,36H,1-3,6,12-13H2,(H,34,42)(H,38,39)(H,40,41)(H,43,44)(H,45,46)
• InChIKey: NZSQEWYDDVANME-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-({5-[bis(carboxymethyl)amino]-5-carboxypentyl}carbamoyl)-2-(2,7-dichloro-6-hydroxy-3-oxo-8a,10a-dihydro-3H-xanthen-9-yl)benzoic acid
• IUPAC Traditional name: 4-({5-[bis(carboxymethyl)amino]-5-carboxypentyl}carbamoyl)-2-(2,7-dichloro-3-hydroxy-6-oxo-4a,9a-dihydroxanthen-9-yl)benzoic acid
• Synonyms: NTA-DFC; N-[5-(Biscarboxymethyl-amino)-5-carboxy-pentyl)]-2-(2,7-dichloro-6-hydroxy-3-oxo-3H-xanthen-9-yl)-terephthalamic Acid

Database IDs

• PubChem SID: 162256372
• PubChem CID: 45038366

CALCULATED PROPERTIES

• Acid pKa: 3.0139015
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): -5.56314
• LogD (pH = 7.4): -11.689978
• Log P: 1.3843825
• Molar Refractivity: 170.7752 cm^3
• Polarizability: 63.062416 Å^3
• Polar Surface Area: 228.07 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Orange Powder
• Melting Point: 182°C dec.

DETAILS

Toronto Research Chemicals - B417200

A small, yet highly fluorescent label for polyhistidine sequences.

REFERENCES

• Goldsmith, C.R., et al.: J.A.C.S., 128, 418 (2006)