(acetyloxy)methyl 2-({2-[(acetyloxy)methoxy]-2-oxoethyl}[2-(5-{[(acetyloxy)methoxy]carbonyl}-1,3-oxazol-2-yl)-5-(2-{2-[bis({2-[(acetyloxy)methoxy]-2-oxoethyl})amino]-5-methylphenoxy}ethoxy)-1-benzofuran-6-yl]amino)acetate

• ChemBase ID: 103582
• Molecular Formular: C44H47N3O24
• Molecular Mass: 1001.84968
• Monoisotopic Mass: 1001.2549494
• SMILES: CC(=O)OCOC(=O)CN(CC(=O)OCOC(=O)C)c1ccc(C)cc1OCCOc1cc2c(oc(c2)c2ncc(o2)C(=O)OCOC(=O)C)cc1N(CC(=O)OCOC(=O)C)CC(=O)OCOC(=O)C
• Canonical SMILES: CC(=O)OCOC(=O)CN(c1cc2oc(cc2cc1OCCOc1cc(C)ccc1N(CC(=O)OCOC(=O)C)CC(=O)OCOC(=O)C)c1ncc(o1)C(=O)OCOC(=O)C)CC(=O)OCOC(=O)C
• InChI: InChI=1S/C44H47N3O24/c1-25-7-8-32(46(16-39(53)65-20-60-26(2)48)17-40(54)66-21-61-27(3)49)35(11-25)58-9-10-59-36-12-31-13-37(43-45-15-38(71-43)44(57)69-24-64-30(6)52)70-34(31)14-33(36)47(18-41(55)67-22-62-28(4)50)19-42(56)68-23-63-29(5)51/h7-8,11-15H,9-10,16-24H2,1-6H3
• InChIKey: VPSRLGDRGCKUTK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (acetyloxy)methyl 2-({2-[(acetyloxy)methoxy]-2-oxoethyl}[2-(5-{[(acetyloxy)methoxy]carbonyl}-1,3-oxazol-2-yl)-5-(2-{2-[bis({2-[(acetyloxy)methoxy]-2-oxoethyl})amino]-5-methylphenoxy}ethoxy)-1-benzofuran-6-yl]amino)acetate
• IUPAC Traditional name: fura-2-acetoxymethyl ester
• Synonyms: 1-[6-Amino-2-(5-carboxy-2-oxazolyl)-5-benzofuranyloxy]-2-(2-amino-5-methylphenoxy) ethane-N,N,N',N'-tetraacetic acid, pentaacetoxymethyl ester; FURA 2-AM; Fura-2AM; Fura-2-acetoxymethyl ester; Fura-2 pentakis(acetoxymethyl) ester; Fura 2-AM

Database IDs

• CAS Number: 108964-32-5
• MDL Number: MFCD00036976
• Beilstein Number: 8183748
• PubChem SID: 24894734; 162102884; 24871658
• PubChem CID: 3364574
• Chemspider ID: 2610364
• Wikipedia Title: Fura-2-acetoxymethyl_ester

CALCULATED PROPERTIES

• H Acceptors: 15
• H Donor: 0
• LogD (pH = 5.5): 1.9595287
• LogD (pH = 7.4): 1.9595287
• Log P: 1.9595287
• Molar Refractivity: 238.0855 cm^3
• Polarizability: 92.136955 Å^3
• Polar Surface Area: 327.11 Å^2
• Rotatable Bonds: 37
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO: soluble
• Apperance: yellow powder
• Fluorescence: λex 355 nm; λem 495 nm in 0.1 M Tris pH 8.0, esterase; 10 mM Ca2+

Safety Information

• Storage Condition: -20°C
• 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: ≥95.0% (HPLC)
• Suitability: suitable for fluorescence
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C44H47N3O24

DETAILS

MP Biomedicals - 02152286

This is the acetoxymethyl ester of FURA 2. Able to permeate cell membranes and load FURA 2 into cells. Inside cells, FURA 2-AM is rapidly hydrolyzed by cytoplasmic esterases.

Sigma Aldrich - 47989

Other Notes
Membrane-permeable derivative of Fura-2. Used to load the chelator into cells. Hydrolysed enzymatically in the cell to yield Fura-2 which remains within the cell1,2,3,4

Sigma Aldrich - F0888

Application
Cell permeable fluorescent probe for Ca2+ used to determine cystolic Ca2+; metabolized in vivo to the active ligand Fura 2.