4-methylumbelliferone (YMDB00971)

Identification
YMDB IDYMDB00971
Name4-methylumbelliferone
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description4-Methylumbelliferone, also known as hymecromone or 4-MU, belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. 4-Methylumbelliferone is an extremely weak basic (essentially neutral) compound (based on its pKa).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • 2H-1-Benzopyran-2-one, 7-hydroxy-4-methyl-
  • 2H-1-Benzopyren-2-one, 7-hydroxy-4-methyl-
  • 4-Methyl-7-Hydroxycoumarin
  • 4-Methylumbelliferon
  • 4-Methylumbelliferone
  • 7-Hydroxy-4-methyl-2-oxo-2H-1-benzopyran
  • 7-Hydroxy-4-methyl-2-oxo-3-chromene
  • 7-Hydroxy-4-methyl-2H-1-benzopyran-2-one
  • 7-Hydroxy-4-methyl-2H-chromen-2-one
  • 7-Hydroxy-4-methylcoumarin
  • beta-Methylumbelliferone
  • Bilcolic
  • Bilicante
  • Biliton H
  • CantabbY
  • Cantabilin
  • Cantabiline
  • Cholestil
  • Cholonerton
  • Cholspasmin
  • Coumarin, 7-hydroxy-4-methyl-
  • Crodimon
  • Cumarote-C
  • Eurogale
  • Himecol
  • Hymecromon
  • Hymecromone
  • Imecromone
  • Imecromonoe
  • Medilla
  • Mendiaxon
  • METHYLUMBELLIFERONE, β
  • Methylumbelliferone, beta
  • Umbelliferone, 4-methyl-
  • 4-MU
  • Himecromona
  • Hymecromonum
  • b-Methylumbelliferone
  • Β-methylumbelliferone
  • 4 Methylumbelliferone
  • Methylumbelliferone
  • Resocyanine
  • 7-Hydroxy-4-methyl-coumarin
  • 7 Hydroxy 4 methyl coumarin
CAS number90-33-5
WeightAverage: 176.1687
Monoisotopic: 176.047344122
InChI KeyHSHNITRMYYLLCV-UHFFFAOYSA-N
InChIInChI=1S/C10H8O3/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5,11H,1H3
IUPAC Name7-hydroxy-4-methyl-2H-chromen-2-one
Traditional IUPAC Name4-methylumbelliferone
Chemical FormulaC10H8O3
SMILESCC1=CC(=O)OC2=CC(O)=CC=C12
Chemical Taxonomy
Description belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent7-hydroxycoumarins
Alternative Parents
Substituents
  • 7-hydroxycoumarin
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point195.5 °C
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogP1.90 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility1.99 g/LALOGPS
logP2.19ALOGPS
logP1.78ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)7.8ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.81 m³·mol⁻¹ChemAxon
Polarizability17.42 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002b-3900000000-9efd3962e332f4fe7d26JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002b-6900000000-936015a6cd7badae842dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f8a-2980000000-3aeee58378773e7d1219JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ugj-2960000000-f6994262beea96fffc26JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f89-2960000000-1ab50bc14647991bd5d2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0faj-2970000000-4b2dc64a826d132a7ac2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fna-9870000000-9adb76fb1e3b45a0c884JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fna-9870000000-4e4875af7ba45d8e6b44JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ugj-2970000000-884a310f76d9d267a70bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002b-3900000000-9efd3962e332f4fe7d26JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-002b-6900000000-936015a6cd7badae842dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f8a-2980000000-3aeee58378773e7d1219JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ugj-2960000000-f6994262beea96fffc26JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f89-2960000000-1ab50bc14647991bd5d2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0faj-2970000000-4b2dc64a826d132a7ac2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fna-9870000000-9adb76fb1e3b45a0c884JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fna-9870000000-4e4875af7ba45d8e6b44JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0ugj-2970000000-884a310f76d9d267a70bJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0059-0900000000-61e4a7e4dde1895885e1JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00ej-5790000000-01d3673ec552268394fbJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-00lr-0900000000-3fbf9ca915c0d92b76b8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-00lr-0900000000-3fbf9ca915c0d92b76b8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-00lr-0900000000-3fbf9ca915c0d92b76b8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0900000000-7310a945d17eac4e2059JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-00b9-0900000000-dbaabe103373f8223a00JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-00lr-0900000000-f5b0dc40956eb4d6a0c3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-15179f6a234b8a7d3cf6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-4a4f4d19d44ec53053cfJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0159-5900000000-67144e5ea0eccd502633JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-afc39113149e898d6ec7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-be2b46a238d108a6f9d3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-004i-0900000000-6e6f0d61b2f7d894a33fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , negativesplash10-001i-0900000000-bb66d78d1350716d5378JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00e9-0900000000-80bbdd2e5005d9ff91ddJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00e9-0900000000-99219a886e7805901941JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-00lr-0900000000-3fbf9ca915c0d92b76b8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-2900000000-4991f1c9aad4efc830aaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-2900000000-dde217681388bfa4bc93JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-86b0f5bf4b6d213d6c7dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-8291807d2225eacd271cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0900000000-ca6205f9f97f55456bf7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002r-4900000000-9f86a6318eefcf9b69ceJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-cc2b1e7f3f612901e8bdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-0900000000-7e08315e76bb28199f32JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0059-2900000000-8e6be50bdb9190fc6a05JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Fia, G., Giovani, G., Rosi, I. (2005). "Study of beta-glucosidase production by wine-related yeasts during alcoholic fermentation. A new rapid fluorimetric method to determine enzymatic activity." J Appl Microbiol 99:509-517.16108792
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17224
HMDB IDHMDB0059622
Pubchem Compound ID5280567
Kegg IDC03081
ChemSpider ID4444190
FOODB IDNot Available
Wikipedia4-methylumbelliferone
BioCyc IDCPD-182

Enzymes

Protein Details
1. S-formylglutathione hydrolase
General function:
Involved in carboxylesterase activity
Specific function:
Serine hydrolase involved in the detoxification of formaldehyde
Gene Name:
Not Available
Uniprot ID:
P40363
Molecular weight:
33934.0
Reactions
S-formylglutathione + H(2)O → glutathione + formate.
4-methylumbelliferyl acetate + H2O → 4-methylumbelliferone + acetate