MiMeDB: Showing metabocard for 4-methylumbelliferone (MMDBc0033194)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:38:33 UTC

Update Date

2024-04-30 20:02:42 UTC

Metabolite ID

MMDBc0033194

Metabolite Identification

Common Name

4-methylumbelliferone

Description

4-methylumbelliferone is a substrate for: Liver carboxylesterase 1, Cocaine esterase, and S-formylglutathione hydrolase.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 4MU                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.339  -1.594   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.673  -0.824   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.673   0.716   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.662   0.716   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.662  -0.824   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.329  -1.594   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.996   1.486   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       1.329   1.486   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.329  -3.134   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.005  -0.824   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.005   0.716   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.339   1.486   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.006   1.486   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1    3                                                       
CONECT    3    2   12   13                                                  
CONECT    4    5    7    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    9   10                                                  
CONECT    7    4                                                            
CONECT    8    4   11                                                       
CONECT    9    6                                                            
CONECT   10    1    6   11                                                  
CONECT   11    8   10   12                                                  
CONECT   12    3   11                                                       
CONECT   13    3                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

Synonyms

Value	Source
4-Methyl-7-hydroxycoumarin	ChEBI
4-MU	ChEBI
7-Hydroxy-4-methyl-2-oxo-2H-1-benzopyran	ChEBI
7-Hydroxy-4-methyl-2-oxo-3-chromene	ChEBI
7-Hydroxy-4-methyl-2H-1-benzopyran-2-one	ChEBI
7-Hydroxy-4-methylcoumarin	ChEBI
beta-Methylumbelliferone	ChEBI
Himecromona	ChEBI
Hymecromone	ChEBI
Hymecromonum	ChEBI
Imecromone	ChEBI
Cantabiline	Kegg
b-Methylumbelliferone	Generator
Β-methylumbelliferone	Generator
4 Methylumbelliferone	HMDB
Methylumbelliferone	HMDB
Resocyanine	HMDB
7-Hydroxy-4-methyl-coumarin	HMDB
Mendiaxon	HMDB
7 Hydroxy 4 methyl coumarin	HMDB
Cholestil	HMDB
4-Methylumbelliferone	MeSH

Molecular Formula

C₁₀H₈O₃

Average Mass

176.1687

Monoisotopic Mass

176.047344122

IUPAC Name

7-hydroxy-4-methyl-2H-chromen-2-one

Traditional Name

4-methylumbelliferone

CAS Registry Number

90-33-5

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 Key

HSHNITRMYYLLCV-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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

7-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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxycoumarin (CHEBI:17224 )
a small molecule (CPD-182 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.99 g/L	ALOGPS
logP	2.19	ALOGPS
logP	1.78	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	7.8	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	47.81 m³·mol⁻¹	ChemAxon
Polarizability	17.42 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-002b-3900000000-9efd3962e332f4fe7d26	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-002b-6900000000-936015a6cd7badae842d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f8a-2980000000-3aeee58378773e7d1219	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ugj-2960000000-f6994262beea96fffc26	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f89-2960000000-1ab50bc14647991bd5d2	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0faj-2970000000-4b2dc64a826d132a7ac2	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fna-9870000000-9adb76fb1e3b45a0c884	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fna-9870000000-4e4875af7ba45d8e6b44	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ugj-2970000000-884a310f76d9d267a70b	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-002b-3900000000-9efd3962e332f4fe7d26	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-002b-6900000000-936015a6cd7badae842d	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f8a-2980000000-3aeee58378773e7d1219	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ugj-2960000000-f6994262beea96fffc26	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0f89-2960000000-1ab50bc14647991bd5d2	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0faj-2970000000-4b2dc64a826d132a7ac2	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fna-9870000000-9adb76fb1e3b45a0c884	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fna-9870000000-4e4875af7ba45d8e6b44	2018-05-18	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ugj-2970000000-884a310f76d9d267a70b	2018-05-18	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0059-0900000000-61e4a7e4dde1895885e1	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00ej-5790000000-01d3673ec552268394fb	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-00lr-0900000000-3fbf9ca915c0d92b76b8	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-00lr-0900000000-3fbf9ca915c0d92b76b8	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-00lr-0900000000-3fbf9ca915c0d92b76b8	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0900000000-7310a945d17eac4e2059	2017-09-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-00b9-0900000000-dbaabe103373f8223a00	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-00lr-0900000000-f5b0dc40956eb4d6a0c3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-0900000000-15179f6a234b8a7d3cf6	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-0900000000-4a4f4d19d44ec53053cf	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-0159-5900000000-67144e5ea0eccd502633	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0900000000-afc39113149e898d6ec7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0900000000-be2b46a238d108a6f9d3	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0900000000-6e6f0d61b2f7d894a33f	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-001i-0900000000-bb66d78d1350716d5378	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00e9-0900000000-80bbdd2e5005d9ff91dd	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00e9-0900000000-99219a886e7805901941	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-00lr-0900000000-3fbf9ca915c0d92b76b8	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-2900000000-4991f1c9aad4efc830aa	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-004i-2900000000-dde217681388bfa4bc93	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-004i-0900000000-86b0f5bf4b6d213d6c7d	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0900000000-8291807d2225eacd271c	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0900000000-ca6205f9f97f55456bf7	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-002r-4900000000-9f86a6318eefcf9b69ce	2016-08-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-cc2b1e7f3f612901e8bd	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-0900000000-7e08315e76bb28199f32	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0059-2900000000-8e6be50bdb9190fc6a05	2016-08-03	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192140	UDP-glucuronosyltransferase 1-1	Enzyme	P22309	Homo sapiens
MMDBp0192154	Liver carboxylesterase 1	Enzyme	P23141	Homo sapiens
MMDBp0192155	Cocaine esterase	Enzyme	O00748	Homo sapiens
MMDBp0192157	S-formylglutathione hydrolase	Enzyme	P10768	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0059622

DrugBank ID

DB07118

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4444190

KEGG Compound ID

C03081

BioCyc ID

CPD-182

BiGG ID

Not Available

Wikipedia Link

Hymecromone

METLIN ID

Not Available

PubChem Compound

5280567

PDB ID

Not Available

ChEBI ID

17224

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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. doi: 10.1016/s0006-291x(02)02516-0. [PubMed:12419303 ]
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. doi: 10.1016/j.cellbi.2007.03.016. Epub 2007 Mar 20. [PubMed:17470403 ]
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 ]

Showing metabocard for 4-methylumbelliferone (MMDBc0033194)

MOL for #<Metabolite:0x00007fecdd7bcd30>

3D MOL for #<Metabolite:0x00007fecdd7bcd30>

3D SDF for #<Metabolite:0x00007fecdd7bcd30>

3D-SDF for #<Metabolite:0x00007fecdd7bcd30>

PDB for #<Metabolite:0x00007fecdd7bcd30>

3D PDB for #<Metabolite:0x00007fecdd7bcd30>

SMILES for #<Metabolite:0x00007fecdd7bcd30>

INCHI for #<Metabolite:0x00007fecdd7bcd30>

Structure for #<Metabolite:0x00007fecdd7bcd30>

3D Structure for #<Metabolite:0x00007fecdd7bcd30>