GLUCOSAMINE

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Search structure


Synonyms	Chitosamine Glucosamine Mediflex
Status
Molecule Category	Free-form
ATC	M01AX05
UNII	N08U5BOQ1K


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	MSWZFWKMSRAUBD-IVMDWMLBSA-N
Smiles	N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O
InChI	InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6?/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C6H13NO5
Molecular Weight	179.17
AlogP	-3.25
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	5.0
Number of Rotational Bond	1.0
Polar Surface Area	116.17
Molecular species	NEUTRAL
Aromatic Rings	0.0
Heavy Atoms	12.0

Bioactivity

Mechanism of Action	Action	Reference
Supplement	None	PubMed DailyMed PubMed

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters	-	-	-	-	14

Assay Description	Organism	Bioactivity	Reference
Antiinflammatory activity against carrageenan-induced paw edema in Wistar rat assessed as reduction of paw edema at 250 mg/kg after 3 hrs relative to control	Rattus norvegicus	15.17 %
Antiinflammatory activity against carrageenan-induced paw edema in Wistar rat assessed as reduction of paw edema at 250 mg/kg after 4 hrs relative to control	Rattus norvegicus	16.12 %
Antiarthritic activity against Mycobacterium tuberculosis-induced rat arthritic model assessed as inhibition of chronic phase inflammation at 250 mg/kg relative to control	Rattus norvegicus	21.61 %
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy	Homo sapiens	13.9 %
Antidegenerative activity against bovine cartilage explant assessed as inhibition of IL1-induced of GAG release at 10 mM for 1 day before IL-1 treatment measured after 6 days by colorimetric analysis relative to control	Bos taurus	19.0 %
Antidegenerative activity against bovine cartilage explant assessed as inhibition of IL1-induced of GAG release at 1 mM for 1 day before IL-1 treatment measured after 6 days by colorimetric analysis relative to control	Bos taurus	3.4 %
Antidegenerative activity against bovine cartilage explant assessed as inhibition of IL1-induced of GAG release at 0.1 mM for 1 day before IL-1 treatment measured after 6 days by colorimetric analysis relative to control	Bos taurus	0.8 %
Antidegenerative activity against human cartilage explant assessed as inhibition of IL1-induced of GAG release at 10 uM for 1 day before IL-1 treatment measured after 6 days by colorimetric analysis relative to control	Homo sapiens	10.3 %
Antidegenerative activity against human cartilage explant assessed as inhibition of IL1-induced of GAG release at 250 uM for 1 day before IL-1 treatment measured after 6 days by colorimetric analysis relative to control	Homo sapiens	14.1 %
Binding affinity to V5-His tagged FIBCD1 ecto-domain (54 to 461 residues) (unknown origin) assessed as reduction in binding between FIBCD1 and acetylated BSA at 50 mM by ELISA relative to control	Homo sapiens	50.0 %

Related Entries

Cross References

Resources	Reference
ChEBI	47977
ChEMBL	CHEMBL493287
DrugBank	DB01296
DrugCentral	1307
FDA SRS	N08U5BOQ1K
Human Metabolome Database	HMDB0001514
KEGG	C00329
PharmGKB	PA164747613
PubChem	3034366
SureChEMBL	SCHEMBL167831

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).