3-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid; 4-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid

• ChemBase ID: 155813
• Molecular Formular: C50H30N2O18
• Molecular Mass: 946.7758
• Monoisotopic Mass: 946.14936213
• SMILES: c1cc(c(c(c1)C(=O)ON1C(=O)CCC1=O)c1c2ccc(cc2oc2cc(=O)ccc12)O)C(=O)O.c1cc(c(cc1C(=O)ON1C(=O)CCC1=O)c1c2ccc(cc2oc2cc(=O)ccc12)O)C(=O)O
• Canonical SMILES: O=c1ccc2c(c1)oc1c(c2c2c(cccc2C(=O)ON2C(=O)CCC2=O)C(=O)O)ccc(c1)O.O=c1ccc2c(c1)oc1c(c2c2cc(ccc2C(=O)O)C(=O)ON2C(=O)CCC2=O)ccc(c1)O
• InChI: InChI=1S/2C25H15NO9/c27-13-2-5-16-19(10-13)34-20-11-14(28)3-6-17(20)23(16)18-9-12(1-4-15(18)24(31)32)25(33)35-26-21(29)7-8-22(26)30;27-12-4-6-14-18(10-12)34-19-11-13(28)5-7-15(19)22(14)23-16(24(31)32)2-1-3-17(23)25(33)35-26-20(29)8-9-21(26)30/h1-6,9-11,27H,7-8H2,(H,31,32);1-7,10-11,27H,8-9H2,(H,31,32)
• InChIKey: YVTPVJDECOUTJW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid; 4-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid
• IUPAC Traditional name: 3-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid; 4-{[(2,5-dioxopyrrolidin-1-yl)oxy]carbonyl}-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
• Synonyms: 5(6)-FAM SE; FLUOS; 5(6)-Carboxyfluorescein N-hydroxysuccinimide ester

Database IDs

• CAS Number: 117548-22-8
• MDL Number: MFCD04119713
• PubChem SID: 162249951; 24853087
• PubChem CID: 16211573

CALCULATED PROPERTIES

• Acid pKa: 3.5519955
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 0.13300191
• LogD (pH = 7.4): -2.1558456
• Log P: 1.8339618
• Molar Refractivity: 131.2226 cm^3
• Polarizability: 45.01695 Å^3
• Polar Surface Area: 147.51 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMF: soluble; DMSO: soluble
• Fluorescence: λex 492 nm; λem 517 nm in DMF

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥80% (HPLC); ≥90% (HPLC)
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C25H15NO9

DETAILS

Sigma Aldrich - 21878

Application
Fluorescent label for primary and secondary amine groups on proteins and other biomolecules.
Has been used to prepare fluorescent derivatives of tubulin and for the preparation of a phenytoin tracer for the determination of this drug in serum and plasma by fluorescence polarization immunoassay (FPIA)

Sigma Aldrich - C1609

Application
Fluorescent label for primary and secondary amine groups on proteins and other biomolecules.
Has been used to prepare fluorescent derivatives of tubulin and for the preparation of a phenytoin tracer for the determination of this drug in serum and plasma by fluorescence polarization immunoassay (FPIA)
Reacts with primary and secondary amine groups on proteins and other biomolecules.