methyl 9-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-8-methoxy-2-oxo-2H-benzo[g]chromene-3-carboxylate

• ChemBase ID: 155992
• Molecular Formular: C20H13NO7
• Molecular Mass: 379.31972
• Monoisotopic Mass: 379.06920176
• SMILES: COc1ccc2cc3cc(c(=O)oc3cc2c1N1C(=O)C=CC1=O)C(=O)OC
• Canonical SMILES: COC(=O)c1cc2cc3ccc(c(c3cc2oc1=O)N1C(=O)C=CC1=O)OC
• InChI: InChI=1S/C20H13NO7/c1-26-14-4-3-10-7-11-8-13(19(24)27-2)20(25)28-15(11)9-12(10)18(14)21-16(22)5-6-17(21)23/h3-9H,1-2H3
• InChIKey: NCSDVQRATCBRRJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl 9-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)-8-methoxy-2-oxo-2H-benzo[g]chromene-3-carboxylate
• IUPAC Traditional name: methyl 9-(2,5-dioxopyrrol-1-yl)-8-methoxy-2-oxobenzo[g]chromene-3-carboxylate
• Synonyms: Methyl 9-maleimido-8-methoxy-2-oxo-2H-naphtho[2,3-b]pyran-3-carboxylate; Methyl 9-maleinimido-8-methoxy-6,7-benzocumarin-3-carboxylate; ThioGlo™-5

Database IDs

• CAS Number: 168639-87-0
• MDL Number: MFCD03453277
• Beilstein Number: 7231414
• PubChem SID: 162250130; 24889949
• PubChem CID: 3283500

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 1.8541207
• LogD (pH = 7.4): 1.8541213
• Log P: 1.8541213
• Molar Refractivity: 97.2731 cm^3
• Polarizability: 37.868618 Å^3
• Polar Surface Area: 99.21 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 285-291 °C
• Fluorescence: λex 285 nm; λem 515 nm±3 nm in 0.1 M phosphate pH 7.0 (after derivatization with glutathione)

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99.0% (TLC)
• Grade: fluorescence indicator
• Empirical Formula (Hill Notation): C20H13NO7

DETAILS

Sigma Aldrich - 94024

Other Notes
SH reactive label; reacts very quickly with proteins; products are more stable (also photostable) to hydolysis than fluorescein maleimide (FM) and 7-diethylamino-3-(4′-maleimidyl phenyl)-4-methyl coumarin (CPM) derivatives, with very large Stokes shift1
Legal Information
ThioGlo is a trademark of Covalent Associates, Inc.