Page last updated: 2024-11-06

4-methylumbelliferyl sulfate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

4-methylumbelliferyl sulfate (4-MUS) is a synthetic compound used as a substrate for the enzyme sulfatase. 4-MUS is hydrolyzed by sulfatases to produce 4-methylumbelliferone, a fluorescent compound that can be easily detected and quantified. This property makes 4-MUS a valuable tool for studying sulfatase activity in various biological samples, including cells, tissues, and biological fluids. 4-MUS is also used in diagnostic assays for sulfatase deficiency diseases, such as mucopolysaccharidoses. The synthesis of 4-MUS involves the reaction of 4-methylumbelliferone with sulfuric acid or sulfuryl chloride. The reaction is typically carried out in an organic solvent, such as pyridine or dimethylformamide, under mild conditions. 4-MUS is a useful tool for research in various fields, including enzymology, biochemistry, and clinical diagnostics.'

4-methylumbelliferyl sulfate: RN given refers to parent cpd [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

4-methylumbelliferone sulfate : A member of the class of coumarins that is umbelliferone sulfate which carries a methyl group at position 4. It is a metabolite of 4-methylumbelliferone. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID84843
CHEMBL ID2074784
CHEBI ID1905
SCHEMBL ID25184
MeSH IDM0071970

Synonyms (24)

Synonym
4-methylumbelliferyl sulfate
25892-63-1
4-methylumbelliferone sulfate
hymecromone sulfate
2h-1-benzopyran-2-one, 4-methyl-7-(sulfooxy)-
(4-methyl-2-oxochromen-7-yl) hydrogen sulfate
AC1L38AP ,
AC1Q6XJI ,
(4-methyl-2-oxidanylidene-chromen-7-yl) hydrogen sulfate
mux ,
CHEMBL2074784
chebi:1905 ,
SCHEMBL25184
4-methyl-7-(sulfooxy)-2h-1-benzopyran-2-one
4-methyl-2-oxo-2h-1-benzopyran-7-yl hydrogen sulfate
7-sulfooxy-4-methylcoumarin
4-methyl-2-oxo-2h-chromen-7-yl hydrogen sulfate
hymecromone 7-sulfate
(4-methyl-2-oxo-chromen-7-yl) hydrogen sulfate
DTXSID60864564
mfcd00870208
Q27105524
W17110
4-methyl-2-oxo-2h-chromen-7-ylhydrogensulfate
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
human xenobiotic metaboliteAny human metabolite produced by metabolism of a xenobiotic compound in humans.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
aryl sulfate
coumarins
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (1)

Other Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Broad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)Km13.00004.00005.40006.8000AID680975
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (14)

Processvia Protein(s)Taxonomy
lipid transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
organic anion transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
urate transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
biotin transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
sphingolipid biosynthetic processBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
riboflavin transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
urate metabolic processBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
transmembrane transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
transepithelial transportBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
renal urate salt excretionBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
export across plasma membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
transport across blood-brain barrierBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
cellular detoxificationBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
xenobiotic transport across blood-brain barrierBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (14)

Processvia Protein(s)Taxonomy
protein bindingBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
ATP bindingBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
organic anion transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
ABC-type xenobiotic transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
urate transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
biotin transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
efflux transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
ATP hydrolysis activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
riboflavin transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
ATPase-coupled transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
identical protein bindingBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
protein homodimerization activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
xenobiotic transmembrane transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
sphingolipid transporter activityBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
nucleoplasmBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
plasma membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
apical plasma membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
brush border membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
mitochondrial membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
membrane raftBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
external side of apical plasma membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
plasma membraneBroad substrate specificity ATP-binding cassette transporter ABCG2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID1624937Substrate activity at Helix pomatia arylsulfatase assessed as enzyme-mediated compound hydrolysis by measuring parent compound remaining using 0.1 U of enzyme measured after 30 mins by UPLC-MS/MS analysis2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Comprehensive kinetic and substrate specificity analysis of an arylsulfatase from Helix pomatia using mass spectrometry.
AID681172TP_TRANSPORTER: uptake (vesicle) in membrane vesicles from ABCG2-expressing P388 cells2003The Journal of biological chemistry, Jun-20, Volume: 278, Issue:25
ABCG2 transports sulfated conjugates of steroids and xenobiotics.
AID680975TP_TRANSPORTER: uptake (vesicle) in membrane vesicle from ABCG2-expressing mouse lymphoma(P388)cells2003The Journal of biological chemistry, Jun-20, Volume: 278, Issue:25
ABCG2 transports sulfated conjugates of steroids and xenobiotics.
AID1624946Substrate activity at Helix pomatia arylsulfatase assessed as enzyme-mediated compound hydrolysis by measuring Vmax by UPLC-MS/MS analysis2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Comprehensive kinetic and substrate specificity analysis of an arylsulfatase from Helix pomatia using mass spectrometry.
AID1624945Substrate activity at Helix pomatia arylsulfatase assessed as enzyme-mediated compound hydrolysis by measuring Km by UPLC-MS/MS analysis2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Comprehensive kinetic and substrate specificity analysis of an arylsulfatase from Helix pomatia using mass spectrometry.
AID1624942Stability of the compound in pH 7 ammonium acetate buffer by UPLC-MS/MS analysis2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Comprehensive kinetic and substrate specificity analysis of an arylsulfatase from Helix pomatia using mass spectrometry.
AID1624943Substrate activity at Helix pomatia arylsulfatase assessed as enzyme-mediated compound hydrolysis using 1 U of enzyme measured after 30 mins by UPLC-MS/MS analysis2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Comprehensive kinetic and substrate specificity analysis of an arylsulfatase from Helix pomatia using mass spectrometry.
AID1624935Substrate activity at Helix pomatia arylsulfatase assessed as enzyme-mediated compound hydrolysis using 5 U of enzyme measured immediately by UPLC-MS/MS analysis2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Comprehensive kinetic and substrate specificity analysis of an arylsulfatase from Helix pomatia using mass spectrometry.
AID1624936Substrate activity at Helix pomatia arylsulfatase assessed as enzyme-mediated compound hydrolysis using 5 U of enzyme measured after 30 mins by UPLC-MS/MS analysis2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Comprehensive kinetic and substrate specificity analysis of an arylsulfatase from Helix pomatia using mass spectrometry.
AID1624948Substrate activity at Helix pomatia arylsulfatase assessed as enzyme-mediated compound hydrolysis by measuring catalytic efficiency by UPLC-MS/MS analysis2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Comprehensive kinetic and substrate specificity analysis of an arylsulfatase from Helix pomatia using mass spectrometry.
AID1624934Drug metabolism in pH 7 ammonium acetate buffer assessed as 7-hydroxy-4-methyl-2H-chromen-2-one formation2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Comprehensive kinetic and substrate specificity analysis of an arylsulfatase from Helix pomatia using mass spectrometry.
AID680203TP_TRANSPORTER: inhibition of E1S uptake (E1S: 0.05 uM, 4-methylumbelliferyl sulfate: 500 uM) in Xenopus laevis oocytes2000The Journal of biological chemistry, Feb-11, Volume: 275, Issue:6
Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta.
AID1624947Substrate activity at Helix pomatia arylsulfatase assessed as enzyme-mediated compound hydrolysis by measuring Kcat by UPLC-MS/MS analysis2019Bioorganic & medicinal chemistry, 03-15, Volume: 27, Issue:6
Comprehensive kinetic and substrate specificity analysis of an arylsulfatase from Helix pomatia using mass spectrometry.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (39)

TimeframeStudies, This Drug (%)All Drugs %
pre-199012 (30.77)18.7374
1990's11 (28.21)18.2507
2000's11 (28.21)29.6817
2010's5 (12.82)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 18.21

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index18.21 (24.57)
Research Supply Index3.69 (2.92)
Research Growth Index4.26 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (18.21)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other39 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]