tetrapotassium 2-[(2-{2-[5-(3-aminopropyl)-2-[bis(carboxylatomethyl)amino]phenoxy]ethoxy}-4-methylphenyl)(carboxylatomethyl)amino]acetate

• ChemBase ID: 81818
• Molecular Formular: C26H29K4N3O10
• Molecular Mass: 699.91576
• Monoisotopic Mass: 699.04012086
• SMILES: N(c1c(cc(cc1)C)OCCOc1c(ccc(c1)CCCN)N(CC(=O)[O-])CC(=O)[O-])(CC(=O)[O-])CC(=O)[O-].[K+].[K+].[K+].[K+]
• Canonical SMILES: NCCCc1ccc(c(c1)OCCOc1cc(C)ccc1N(CC(=O)[O-])CC(=O)[O-])N(CC(=O)[O-])CC(=O)[O-].[K+].[K+].[K+].[K+]
• InChI: InChI=1S/C26H33N3O10.4K/c1-17-4-6-19(28(13-23(30)31)14-24(32)33)21(11-17)38-9-10-39-22-12-18(3-2-8-27)5-7-20(22)29(15-25(34)35)16-26(36)37;;;;/h4-7,11-12H,2-3,8-10,13-16,27H2,1H3,(H,30,31)(H,32,33)(H,34,35)(H,36,37);;;;/q;4*+1/p-4
• InChIKey: KQVVJEZWKUHNGT-UHFFFAOYSA-J

NAMES AND DATABASE IDS

Names

• IUPAC name: tetrapotassium 2-[(2-{2-[5-(3-aminopropyl)-2-[bis(carboxylatomethyl)amino]phenoxy]ethoxy}-4-methylphenyl)(carboxylatomethyl)amino]acetate
• IUPAC Traditional name: tetrapotassium ion 2-[(2-{2-[5-(3-aminopropyl)-2-[bis(carboxylatomethyl)amino]phenoxy]ethoxy}-4-methylphenyl)(carboxylatomethyl)amino]acetate; tetrapotassium 2-[(2-{2-[5-(3-aminopropyl)-2-[bis(carboxylatomethyl)amino]phenoxy]ethoxy}-4-methylphenyl)(carboxylatomethyl)amino]acetate
• Synonyms: BAPTA-APM; 5-(3-Aminopropyl)-5'-methyl-bis-(2-aminophenoxy-methylene)-N,N,N',N'-tetraacetate, tetrapotassium salt; N-[4-(3-Aminopropyl)-2-[2-[2-[bis(carboxymethyl)amino]-5-methylphenoxy]ethoxy]phenyl]-N-(carboxymethyl)glycine Tetrapotassium Salt; 5-(3-Aminopropyl)-5'-methyl-bis-(2-aminophenoxymethylene-N,N,N',N'-tetraacetate Tetrapotassium Salt; BAPTA-APM

Database IDs

• CAS Number: 352000-08-9
• MDL Number: MFCD08445442
• PubChem SID: 162068937
• PubChem CID: 2735436

CALCULATED PROPERTIES

• Acid pKa: 2.888716
• H Acceptors: 13
• H Donor: 1
• LogD (pH = 5.5): -5.5620255
• LogD (pH = 7.4): -10.202028
• Log P: -0.6146979
• Molar Refractivity: 182.488 cm^3
• Polarizability: 52.5072 Å^3
• Polar Surface Area: 211.48 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Ethanol; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: >190°C (dec.); 255-260°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Storage Warning: Irritant/Store at -20°C

DETAILS

Apollo Scientific Ltd - OR2450

A new fluorescent chelating indicator to study the physiological role of free cytosolic calcium.

Toronto Research Chemicals - B124500

BAPTA-APM is a lipophilic diester of BAPTA used for inhibition of proteolytic activities of certain metalloproteinases, calpain and TACE.

REFERENCES

• Li, B., et al.: Brain Res., 1226, 199 (2008)
• Chen, W., et al.: Mol. Endocrinol., 22, 1754 (2008)
• Tonkikh, A., et al.: Neurosci., 159, 1300 (2008)