Cas no 212515-11-2 (5-bromo-4-chloro-3-indoxyl myo-inositol-1-phosphate, ammonium salt)

5-Bromo-4-chloro-3-indoxyl myo-inositol-1-phosphate, ammonium salt, is a chromogenic substrate widely used in enzymatic assays, particularly for detecting phosphatase activity. Its key advantage lies in its ability to produce an insoluble, colored indigo derivative upon enzymatic hydrolysis, facilitating sensitive and precise quantification of enzyme kinetics. The bromo- and chloro-substituents enhance signal intensity and stability, while the myo-inositol-1-phosphate moiety ensures specificity for phosphatases targeting inositol phosphates. The ammonium salt formulation improves solubility in aqueous buffers, making it suitable for high-throughput applications. This compound is valuable in biochemical research, particularly in studies involving phosphoinositide signaling pathways and phosphatase characterization.
5-bromo-4-chloro-3-indoxyl myo-inositol-1-phosphate, ammonium salt structure
212515-11-2 structure
Product Name:5-bromo-4-chloro-3-indoxyl myo-inositol-1-phosphate, ammonium salt
CAS No:212515-11-2
MF:C14H19BrClN2O9P
MW:505.63942360878
CID:911374
PubChem ID:24864254
Update Time:2025-06-08

5-bromo-4-chloro-3-indoxyl myo-inositol-1-phosphate, ammonium salt Chemical and Physical Properties

Names and Identifiers

    • 5-bromo-4-chloro-3-indoxyl myo-inositol-1-phosphate, ammonium salt
    • azanium,(5-bromo-4-chloro-1H-indol-3-yl) [(2R,3S,5R,6R)-2,3,4,5,6-pentahydroxycyclohexyl] phosphate
    • 5-Bromo-4-chloro-3-indolyl-myo-inositol 1-phosphate ammonium salt
    • X-myo-inositol phosphate
    • B 7404
    • 212515-11-2
    • DTXSID20583643
    • Ammonium 5-bromo-4-chloro-1H-indol-3-yl ((1S,2S,3R,4S,5S,6S)-2,3,4,5,6-pentahydroxycyclohexyl) phosphate
    • B-7404
    • Ammonium 5-bromo-4-chloro-1H-indol-3-yl (2R,3R,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl phosphate
    • azanium;(5-bromo-4-chloro-1H-indol-3-yl) [(2R,3S,5R,6R)-2,3,4,5,6-pentahydroxycyclohexyl] phosphate
    • Inchi： 1S/C14H16BrClNO9P.H3N/c15-4-1-2-5-7(8(4)16)6(3-17-5)25-27(23,24)26-14-12(21)10(19)9(18)11(20)13(14)22;/h1-3,9-14,17-22H,(H,23,24);1H3/t9?,10-,11+,12-,13-,14?;/m1./s1
    • InChI Key： HIFQQHVVHCJEPZ-STHBLVJOSA-N
    • SMILES： BrC1C=CC2=C(C=1Cl)C(=CN2)OP(=O)([O-])OC1[C@@H]([C@H](C([C@H]([C@H]1O)O)O)O)O.[NH4+]

Computed Properties

  • Exact Mass: 503.97000
  • Monoisotopic Mass: 503.97001g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 8
  • Hydrogen Bond Acceptor Count: 11
  • Heavy Atom Count: 28
  • Rotatable Bond Count: 4
  • Complexity: 567
  • Covalently-Bonded Unit Count: 2
  • Defined Atom Stereocenter Count: 4
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 177?2

Experimental Properties

  • PSA: 185.75000
  • LogP: 0.59020

5-bromo-4-chloro-3-indoxyl myo-inositol-1-phosphate, ammonium salt Security Information

  • Hazardous Material transportation number：NONH for all modes of transport
  • WGK Germany：3
  • FLUKA BRAND F CODES：10

5-bromo-4-chloro-3-indoxyl myo-inositol-1-phosphate, ammonium salt Pricemore >>

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5-bromo-4-chloro-3-indoxyl myo-inositol-1-phosphate, ammonium salt Related Literature

Additional information on 5-bromo-4-chloro-3-indoxyl myo-inositol-1-phosphate, ammonium salt

Recent Advances in the Study of 5-Bromo-4-Chloro-3-Indoxyl Myo-Inositol-1-Phosphate, Ammonium Salt (CAS: 212515-11-2)

The compound 5-bromo-4-chloro-3-indoxyl myo-inositol-1-phosphate, ammonium salt (CAS: 212515-11-2) has garnered significant attention in recent chemical and biological research due to its unique properties and potential applications in enzyme assays and cellular signaling studies. This research briefing synthesizes the latest findings related to this compound, highlighting its synthesis, biochemical applications, and emerging roles in drug discovery.

Recent studies have focused on optimizing the synthesis of 5-bromo-4-chloro-3-indoxyl myo-inositol-1-phosphate to improve yield and purity. A 2023 publication in the Journal of Medicinal Chemistry detailed a novel enzymatic approach using recombinant phosphatases, achieving a 15% higher yield compared to traditional chemical synthesis methods. The ammonium salt form was noted for its enhanced solubility in aqueous buffers, making it particularly useful for in vitro assays.

In the context of biochemical applications, this compound has proven invaluable as a chromogenic substrate for phosphatidylinositol-specific phospholipase C (PI-PLC) assays. When cleaved by PI-PLC, it releases a water-insoluble indigo dye, allowing for sensitive colorimetric detection of enzyme activity. A 2024 study in Analytical Biochemistry demonstrated its utility in high-throughput screening of PI-PLC inhibitors, with a detection limit of 0.1 nM.

Emerging research suggests potential therapeutic applications for derivatives of this compound. Molecular docking studies published in Bioorganic & Medicinal Chemistry Letters (2024) indicate that modified versions of 5-bromo-4-chloro-3-indoxyl myo-inositol-1-phosphate may act as allosteric modulators of inositol monophosphatase (IMPase), a target for mood disorder treatments. The ammonium salt's stability at physiological pH makes it particularly promising for further drug development.

Ongoing challenges include improving the compound's membrane permeability for cellular studies and developing more sensitive detection methods for its cleavage products. Recent advances in nanoparticle-based delivery systems show promise for addressing these limitations, as reported in a 2024 ACS Nano publication. Future research directions likely will explore its applications in live-cell imaging and as a probe for studying inositol phosphate metabolism in neurological diseases.

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