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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-10-30 10:32:48 UTC
Update Date2019-07-23 07:12:36 UTC
HMDB IDHMDB0059622
Secondary Accession Numbers
  • HMDB59622
Metabolite Identification
Common Name4-Methylumbelliferone
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). 4-methylumbelliferone is a substrate for: Liver carboxylesterase 1, Cocaine esterase, and S-formylglutathione hydrolase.
Structure
Data?1563865956
Synonyms
ValueSource
4-Methyl-7-hydroxycoumarinChEBI
4-MUChEBI
7-Hydroxy-4-methyl-2-oxo-2H-1-benzopyranChEBI
7-Hydroxy-4-methyl-2-oxo-3-chromeneChEBI
7-Hydroxy-4-methyl-2H-1-benzopyran-2-oneChEBI
7-Hydroxy-4-methylcoumarinChEBI
beta-MethylumbelliferoneChEBI
HimecromonaChEBI
HymecromoneChEBI
HymecromonumChEBI
ImecromoneChEBI
CantabilineKegg
b-MethylumbelliferoneGenerator
Β-methylumbelliferoneGenerator
4 MethylumbelliferoneHMDB
MethylumbelliferoneHMDB
ResocyanineHMDB
7-Hydroxy-4-methyl-coumarinHMDB
MendiaxonHMDB
7 Hydroxy 4 methyl coumarinHMDB
CholestilHMDB
4-MethylumbelliferoneMeSH
Chemical FormulaC10H8O3
Average Molecular Weight176.1687
Monoisotopic Molecular Weight176.047344122
IUPAC Name7-hydroxy-4-methyl-2H-chromen-2-one
Traditional Name4-methylumbelliferone
CAS Registry NumberNot Available
SMILES
CC1=CC(=O)OC2=C1C=CC(O)=C2
InChI Identifier
InChI=1S/C10H8O3/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5,11H,1H3
InChI KeyHSHNITRMYYLLCV-UHFFFAOYSA-N
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
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.99 g/LALOGPS
logP10(2.19) g/LALOGPS
logP10(1.78) g/LChemAxon
logS10(-2) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.91231661259
DarkChem[M-H]-134.42831661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
4-MethylumbelliferoneCC1=CC(=O)OC2=C1C=CC(O)=C22843.3Standard polar33892256
4-MethylumbelliferoneCC1=CC(=O)OC2=C1C=CC(O)=C21904.8Standard non polar33892256
4-MethylumbelliferoneCC1=CC(=O)OC2=C1C=CC(O)=C22064.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
4-Methylumbelliferone,1TMS,isomer #1CC1=CC(=O)OC2=CC(O[Si](C)(C)C)=CC=C122048.6Semi standard non polar33892256
4-Methylumbelliferone,1TBDMS,isomer #1CC1=CC(=O)OC2=CC(O[Si](C)(C)C(C)(C)C)=CC=C122299.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone EI-B (Non-derivatized)splash10-002b-3900000000-9efd3962e332f4fe7d262017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone EI-B (Non-derivatized)splash10-002b-6900000000-936015a6cd7badae842d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0f8a-2980000000-3aeee58378773e7d12192017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0ugj-2960000000-f6994262beea96fffc262017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0f89-2960000000-1ab50bc14647991bd5d22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0faj-2970000000-4b2dc64a826d132a7ac22017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0fna-9870000000-9adb76fb1e3b45a0c8842017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0fna-9870000000-4e4875af7ba45d8e6b442017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0ugj-2970000000-884a310f76d9d267a70b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone EI-B (Non-derivatized)splash10-002b-3900000000-9efd3962e332f4fe7d262018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone EI-B (Non-derivatized)splash10-002b-6900000000-936015a6cd7badae842d2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0f8a-2980000000-3aeee58378773e7d12192018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0ugj-2960000000-f6994262beea96fffc262018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0f89-2960000000-1ab50bc14647991bd5d22018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0faj-2970000000-4b2dc64a826d132a7ac22018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0fna-9870000000-9adb76fb1e3b45a0c8842018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0fna-9870000000-4e4875af7ba45d8e6b442018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 4-Methylumbelliferone GC-EI-TOF (Non-derivatized)splash10-0ugj-2970000000-884a310f76d9d267a70b2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methylumbelliferone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0059-0900000000-61e4a7e4dde1895885e12016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methylumbelliferone GC-MS (1 TMS) - 70eV, Positivesplash10-00ej-5790000000-01d3673ec552268394fb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 4-Methylumbelliferone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone ESI-TOF 30V, Negative-QTOFsplash10-00lr-0900000000-3fbf9ca915c0d92b76b82017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone ESI-TOF , Negative-QTOFsplash10-00lr-0900000000-3fbf9ca915c0d92b76b82017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone ESI-TOF 30V, Negative-QTOFsplash10-00lr-0900000000-3fbf9ca915c0d92b76b82017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone ESI-TOF , Negative-QTOFsplash10-004i-0900000000-7310a945d17eac4e20592017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone DI-ESI-qTof , Positive-QTOFsplash10-00b9-0900000000-dbaabe103373f8223a002017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone DI-ESI-qTof , Negative-QTOFsplash10-00lr-0900000000-f5b0dc40956eb4d6a0c32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-QTOF , negative-QTOFsplash10-004i-0900000000-15179f6a234b8a7d3cf62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-QTOF , negative-QTOFsplash10-004i-0900000000-4a4f4d19d44ec53053cf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-QTOF , negative-QTOFsplash10-0159-5900000000-67144e5ea0eccd5026332017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-afc39113149e898d6ec72017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-be2b46a238d108a6f9d32017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-ITFT , negative-QTOFsplash10-004i-0900000000-6e6f0d61b2f7d894a33f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-ITFT , negative-QTOFsplash10-001i-0900000000-bb66d78d1350716d53782017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone Linear Ion Trap , negative-QTOFsplash10-00e9-0900000000-80bbdd2e5005d9ff91dd2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone Linear Ion Trap , negative-QTOFsplash10-00e9-0900000000-99219a886e78059019412017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-TOF , negative-QTOFsplash10-00lr-0900000000-3fbf9ca915c0d92b76b82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-QTOF , positive-QTOFsplash10-004i-2900000000-4991f1c9aad4efc830aa2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-QTOF , positive-QTOFsplash10-004i-2900000000-dde217681388bfa4bc932017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 4-Methylumbelliferone LC-ESI-ITFT , positive-QTOFsplash10-004i-0900000000-86b0f5bf4b6d213d6c7d2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylumbelliferone 10V, Positive-QTOFsplash10-004i-0900000000-8291807d2225eacd271c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylumbelliferone 20V, Positive-QTOFsplash10-004i-0900000000-ca6205f9f97f55456bf72016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylumbelliferone 40V, Positive-QTOFsplash10-002r-4900000000-9f86a6318eefcf9b69ce2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylumbelliferone 10V, Negative-QTOFsplash10-004i-0900000000-cc2b1e7f3f612901e8bd2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylumbelliferone 20V, Negative-QTOFsplash10-004i-0900000000-7e08315e76bb28199f322016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 4-Methylumbelliferone 40V, Negative-QTOFsplash10-0059-2900000000-8e6be50bdb9190fc6a052016-08-03Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB07118
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4444190
KEGG Compound IDC03081
BioCyc IDCPD-182
BiGG IDNot Available
Wikipedia LinkHymecromone
METLIN IDNot Available
PubChem Compound5280567
PDB IDNot Available
ChEBI ID17224
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nakamura T, Ishikawa T, Nanashima N, Miura T, Nozaka H, Nakaoka R, Sato T: 4-Methylumbelliferone induces the expression of membrane type 1-matrix metalloproteinase in cultured human skin fibroblasts. Biochem Biophys Res Commun. 2002 Nov 15;298(5):646-50. [PubMed:12419303 ]
  2. Nakamura R, Kuwabara H, Yoneda M, Yoshihara S, Ishikawa T, Miura T, Nozaka H, Nanashima N, Sato T, Nakamura T: Suppression of matrix metalloproteinase-9 by 4-methylumbelliferone. Cell Biol Int. 2007 Sep;31(9):1022-6. Epub 2007 Mar 20. [PubMed:17470403 ]
  3. Saito T, Tamura D, Nakamura T, Makita Y, Ariyama H, Komiyama K, Yoshihara T, Asano R: 4-methylumbelliferone leads to growth arrest and apoptosis in canine mammary tumor cells. Oncol Rep. 2013 Jan;29(1):335-42. doi: 10.3892/or.2012.2100. Epub 2012 Oct 23. [PubMed:23124556 ]

Enzymes

General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
4-Methylumbelliferone → 3,4,5-trihydroxy-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylic aciddetails
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
4-Methylumbelliferyl acetate + Water → 4-Methylumbelliferone + Acetic aciddetails
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine.
Gene Name:
CES2
Uniprot ID:
O00748
Molecular weight:
68898.39
Reactions
4-Methylumbelliferyl acetate + Water → 4-Methylumbelliferone + Acetic aciddetails
General function:
Involved in carboxylesterase activity
Specific function:
Serine hydrolase involved in the detoxification of formaldehyde.
Gene Name:
ESD
Uniprot ID:
P10768
Molecular weight:
31462.545
Reactions
4-Methylumbelliferyl acetate + Water → 4-Methylumbelliferone + Acetic aciddetails