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4-Methylumbelliferyl glucoside

PubChem CID
2733779
Structure
4-Methylumbelliferyl glucoside_small.png
4-Methylumbelliferyl glucoside_3D_Structure.png
Molecular Formula
Synonyms
  • 18997-57-4
  • 4-Methylumbelliferyl glucoside
  • 4-Methylumbelliferyl-beta-D-glucopyranoside
  • 4-Methylumbelliferyl beta-D-glucopyranoside
  • 4-Methylumbelliferyl |A-D-Glucopyranoside
Molecular Weight
338.31 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-07-19
  • Modify:
    2025-01-18
Description
4-methylumbelliferyl beta-D-glucoside is a beta-D-glucoside having a 4-methylumbelliferyl substituent at the anomeric position. It has a role as a chromogenic compound. It is a member of coumarins, a monosaccharide derivative and a beta-D-glucoside. It is functionally related to a 4-methylumbelliferone.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
4-Methylumbelliferyl glucoside.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-methyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C16H18O8/c1-7-4-12(18)23-10-5-8(2-3-9(7)10)22-16-15(21)14(20)13(19)11(6-17)24-16/h2-5,11,13-17,19-21H,6H2,1H3/t11-,13-,14+,15-,16-/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

YUDPTGPSBJVHCN-YMILTQATSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC1=CC(=O)OC2=C1C=CC(=C2)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C16H18O8
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 ChEBI ID

2.3.4 ChEMBL ID

2.3.5 DrugBank ID

2.3.6 DSSTox Substance ID

2.3.7 Metabolomics Workbench ID

2.3.8 Nikkaji Number

2.3.9 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 4-methylumbelliferyl glucoside
  • 4-methylumbelliferyl glucoside, (alpha)-isomer
  • 4-methylumbelliferyl-alpha-D-glucopyranoside
  • 4-methylumbelliferyl-beta-D-glucopyranoside
  • 4-MU-alpha-glucoside
  • 4-MU-glucoside
  • MUbetaGlu

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
338.31 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
-0.8
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
338.10016753 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
338.10016753 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
126 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
24
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
506
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
5
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Physical Description

White solid; [Sigma-Aldrich MSDS]

3.2.2 Dissociation Constants

Acidic pKa
2.82
Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds. Pharm Res. 2014; 31(4):1082-95. DOI:10.1007/s11095-013-1232-z. PMID:24249037

3.3 Chemical Classes

Other Uses -> Biochemical Research

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

Instrument Name
Varian CFT-20
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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4.1.2 13C NMR Spectra

Source of Sample
Fluka AG, Buchs, Switzerland
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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4.2 Mass Spectrometry

4.2.1 LC-MS

1 of 12
View All
Authors
Nogawa T, Okano A, CSRS, RIKEN
Instrument
ABSciex API3200 LC/MS system
Instrument Type
LC-ESI-QQQ
MS Level
MS
Ionization Mode
POSITIVE
Precursor Adduct
[M+H]+
Top 5 Peaks

177.3 999

339.2 998

339 960

338.7 853

339.1 803

Thumbnail
Thumbnail
License
CC BY
2 of 12
View All
Authors
Nogawa T, Okano A, CSRS, RIKEN
Instrument
Agilent 6410 Triple Quadrupole LC/MS system
Instrument Type
LC-ESI-QQQ
MS Level
MS2
Ionization Mode
POSITIVE
Precursor Adduct
[M+H]+
Top 5 Peaks

177.1 99

177.2 97

177 93

177.3 86

176.9 79

Thumbnail
Thumbnail
License
CC BY

4.3 IR Spectra

4.3.1 FTIR Spectra

Technique
KBr WAFER
Source of Sample
Fluka Chemie AG, Buchs, Switzerland
Catalog Number
69600
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 Biochemical Reactions

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 GHS Classification

Note
This chemical does not meet GHS hazard criteria for 100% (3 of 3) of all reports. Pictograms displayed are for < 0.1% (0 of 3) of reports that indicate hazard statements.
GHS Hazard Statements

Not Classified

Reported as not meeting GHS hazard criteria by 3 of 3 companies. For more detailed information, please visit ECHA C&L website.

ECHA C&L Notifications Summary

Aggregated GHS information provided per 3 reports by companies from 1 notifications to the ECHA C&L Inventory.

Reported as not meeting GHS hazard criteria per 3 of 3 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 0 notifications provided by 0 of 3 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

8.1.2 Hazard Classes and Categories

Not Classified

8.1.3 Hazards Summary

May cause irritation; [Sigma-Aldrich MSDS]

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Springer Nature References

9.4 Nature Journal References

9.5 Chemical Co-Occurrences in Literature

9.6 Chemical-Gene Co-Occurrences in Literature

9.7 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 WIPO PATENTSCOPE

10.3 Chemical Co-Occurrences in Patents

10.4 Chemical-Disease Co-Occurrences in Patents

10.5 Chemical-Gene Co-Occurrences in Patents

11 Interactions and Pathways

11.1 Chemical-Target Interactions

11.2 Drug-Drug Interactions

11.3 Pathways

12 Biological Test Results

12.1 BioAssay Results

13 Classification

13.1 MeSH Tree

13.2 ChEBI Ontology

13.3 ChEMBL Target Tree

13.4 UN GHS Classification

13.5 NORMAN Suspect List Exchange Classification

13.6 EPA DSSTox Classification

13.7 MolGenie Organic Chemistry Ontology

14 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
    4-Methylumbelliferyl β-D-glucopyranoside
    https://commonchemistry.cas.org/detail?cas_rn=18997-57-4
  2. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
    4-methylumbelliferyl beta-D-glucoside
    https://www.drugbank.ca/drugs/DB13177
  3. EPA DSSTox
    4-Methylumbelliferyl β-D-glucopyranoside
    https://comptox.epa.gov/dashboard/DTXSID901275261
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    7-(β-D-glucopyranosyloxy)-4-methyl-2H-1-benzopyran-2-one
    https://echa.europa.eu/substance-information/-/substanceinfo/100.038.836
    7-(β-D-glucopyranosyloxy)-4-methyl-2H-1-benzopyran-2-one (EC: 242-736-7)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/41058
  5. ChEBI
  6. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  7. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  8. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
    4-Methylumbelliferyl glucoside
    https://haz-map.com/Agents/11186
  9. Japan Chemical Substance Dictionary (Nikkaji)
  10. MassBank Europe
    7-Hydroxy-4-methyl-2H-1-benzopyran-2-one, 9CI, O-beta-D-Glucopyranoside
    https://massbank.eu/MassBank/Result.jsp?inchikey=YUDPTGPSBJVHCN-YMILTQATSA-N
  11. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  12. Metabolomics Workbench
  13. Nature Chemical Biology
  14. SpectraBase
    7-[(beta-D-GLUCOPYRANOSYL)OXY]-4-METHYLCOUMARIN
    https://spectrabase.com/spectrum/FRV6E9nY9Ae
    7-[(beta-D-glucopyranosyl)oxy]-4-methylcoumarin
    https://spectrabase.com/spectrum/CHTx3udBBVV
    7-[(beta-D-GLUCOPYRANOSYL)OXY]-4-METHYLCOUMARIN
    https://spectrabase.com/spectrum/HuC0MhKHSaI
  15. Springer Nature
  16. Wikidata
    4-Methylumbelliferyl-beta-D-Glucose
    https://www.wikidata.org/wiki/Q27093599
  17. PubChem
  18. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    4-methylumbelliferyl glucoside
    https://www.ncbi.nlm.nih.gov/mesh/67014110
  19. GHS Classification (UNECE)
  20. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  21. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  22. PATENTSCOPE (WIPO)
CONTENTS