4-Methylumbelliferyl beta-D-glucuronide

HCID 91553
NotesReactions
Substructure searchFind similar structures

Basic information

CAS
6160-80-1
Standard SMILES
Cc1cc(=O)oc2cc(O[C@@H]3O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]3O)ccc12
InChIKey
ARQXEQLMMNGFDU-JHZZJYKESA-N
Molecular formula
C16H16O9
Average molar mass
352.29 g/mol
Monoisotopic mass
352.07943209

Overview

4-methylumbelliferone beta-D-glucuronide is a beta-D-glucosiduronic acid having a 4-methylumbelliferyl substituent at the anomeric position. A hyaluronan synthesis inhibitor, it is anti-tumourigenic for various malignant tumours. It has a role as a hyaluronan synthesis inhibitor, an antineoplastic agent and a chromogenic compound. It is a beta-D-glucosiduronic acid, a member of coumarins and a monosaccharide derivative. It is functionally related to a 4-methylumbelliferone. It is a conjugate acid of a 4-methylumbelliferone beta-D-glucuronide(1-).

Names & identifiers

Preferred name
4-Methylumbelliferyl beta-D-glucuronide
IUPAC
(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-methyl-2-oxochromen-7-yl)oxyoxane-2-carboxylic acid
English name
4-Methylumbelliferyl-beta-D-glucuronide
Molecular formula
C16H16O9
Molecular weight
352.3

Names & synonyms

6160-80-14-Methylumbelliferyl-beta-D-glucuronide4-Methylumbelliferyl glucuronide4-Methylumbelliferyl beta-glucuronidehymecromone glucuronide4-METHYLUMBELLIFERYL beta-D-GLUCURONIDE4-MUGDTXSID10891502(2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-methyl-2-oxo-chromen-7-yl)oxy-tetrahydropyran-2-carboxylic acidbeta-D-Glucopyranosiduronic acid, 4-methyl-2-oxo-2H-1-benzopyran-7-ylRefChem:912705DTXCID101030603
Show more names
4-methylumbelliferylglucuronideMUGMUGLCU4MU-GlcA4-MUG trihydrate4-Mu-beta-d-glca dihydrateHymecromone-beta-D-Glucuronide4-MethylumbelliferylalucuronideMethylumbelliferyl-b-D-glucuronide
228-186-04-Methylumbelliferone glucuronide(2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-((4-methyl-2-oxo-2H-chromen-7-yl)oxy)tetrahydro-2H-pyran-2-carboxylic acid4-methylumbelliferone beta-d-glucuronide4-methylumbelliferyl--d-glucuronideMUG trihydrate4-Methylumbelliferyl-|A-D-glucuronideMolMap_000057

Database identifiers

CAS
6160-80-1
PubChem CID
91553
DTXSID
DTXSID10891502
ChEMBL
CHEMBL1592343
ChEBI
CHEBI:1904
EC Number
228-186-0
Nikkaji
J211.426G

Properties

Computed structural properties

XLogP
-0.5
Topological polar surface area
143 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
9
Rotatable bonds
3
Heavy atoms
25

Experimental & physicochemical properties

LogP-0.39

Physicochemical properties

Melting point
102 °C · 102 °C
alpha
-105 · -105 º (c=0.25, water 30 ºC)
Boiling point
683.1 · 683.1±55.0 °C(Predicted)
Density
1.632 · 1.632±0.06 g/cm3(Predicted)
storage temp.
20 °C · −20°C
solubility
Methanol (Slightly), Water (Slightly)

Safety & regulation

GHS classification

GHS Classification · 3 items

This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.

Not Classified

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 3 items

Chemical: .beta.-D-Glucopyranosiduronic acid, 4-methyl-2-oxo-2H-1-benzopyran-7-yl

PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

.beta.-D-Glucopyranosiduronic acid, 4-methyl-2-oxo-2H-1-benzopyran-7-yl: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

Hazard Classes and CategoriesNot Classified

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
hs_code
29329990
risk_code
22-40
Signal word
Warning

Chemistry & industry

Pharmacology

Metabolism/Metabolites4-Methylumbelliferone O-glucuronide is a known human metabolite of 4-Methylumbelliferone.
MeSH Pharmacological Classification · 1 item

Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags.

Uses & manufacturing

General Manufacturing Information.beta.-D-Glucopyranosiduronic acid, 4-methyl-2-oxo-2H-1-benzopyran-7-yl: ACTIVE
Applications · 4 items

Description4-Methylumbelliferyl-beta-D-glucuronide is a fluorescent substrate of β-glucuronidase. Once cleaved, 4-Methylumbelliferyl-beta-D-glucuronide yields blue fluorescence seen under UV light which is pH-dependent with excitation maxima of 320 and 360 nm at low (1.97-6.72) and high (7.12-10.3) pH, respectively. It is ideal for working with Escherichia coli and plant molecular studies.

Uses4-Methylumbelliferyl β-D-glucuronide dihydrate is a useful building block and a fluorophore.

Uses4-Methylumbelliferyl-beta-D-glucuronide is a substrate for glucuronidase. Also used as a test for coliform bacteria in water. Fluorescence: max. Abs. 316nm; max. Em. 375nm; e x 10-3: 12

UsesSubstrate for -D-glucuronidase assay. MUG is widely used as component of selective microbial culture media.

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
上海康朗生物科技有限公司021-61998208 18217752821 · [email protected]
河北创海生物科技有限公司+86-86-13131129325 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]

Additional notes

DefinitionChEBI: A beta-D-glucosiduronic acid having a 4-methylumbelliferyl substituent at the anomeric position.

Related reactions

4 records
New reaction record

Compound notes

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