MiMeDB: Showing metabocard for Glucosamine (MMDBc0000199)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:39:29 UTC

Update Date

2024-04-30 19:31:27 UTC

Metabolite ID

MMDBc0000199

Metabolite Identification

Common Name

Glucosamine

Description

In the United States, glucosamine is not approved by the Food and Drug Administration for medical use in humans. Since glucosamine is classified as a dietary supplement, evidence of safety and efficacy is not required as long as it is not advertised as a treatment for a medical condition. Nevertheless, glucosamine is a popular alternative medicine used by consumers for the treatment of osteoarthritis. Glucosamine is also extensively used in veterinary medicine as an unregulated but widely accepted supplement (Nolen RS, 2002). Treatment with oral glucosamine is commonly used for the treatment of osteoarthritis. Since glucosamine is a precursor for glycosaminoglycans, and glycosaminoglycans are a major component of joint cartilage, supplemental glucosamine may help to rebuild cartilage and treat arthritis. However, there is little evidence that any clinical effect of glucosamine works this way (Laverty et al., 2005; Biggee et al., 2005). Its use as a therapy for osteoarthritis appears safe but there is conflicting evidence as to its effectiveness. Glucosamine (C6H14NO5) is an amino sugar that is an important precursor in the biochemical synthesis of glycosylated proteins and lipids.

Structure

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

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1296                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       7.908  -0.146   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       3.907   2.164   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0       3.907  -0.916   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       9.242   2.164   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       7.908  -3.226   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0       6.574   3.704   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       5.241   1.394   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.241  -0.146   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.574   2.164   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.574  -0.916   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.908   1.394   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.574  -2.456   0.000  0.00  0.00           C+0
CONECT    1   10   11                                                       
CONECT    2    7                                                            
CONECT    3    8                                                            
CONECT    4   11                                                            
CONECT    5   12                                                            
CONECT    6    9                                                            
CONECT    7    2    8    9                                                  
CONECT    8    3    7   10                                                  
CONECT    9    6    7   11                                                  
CONECT   10    1    8   12                                                  
CONECT   11    1    4    9                                                  
CONECT   12    5   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

Synonyms

Value	Source
2-Amino-2-deoxy-D-glucose	ChEBI
Chitosamine	ChEBI
D-Glucosamine	ChEBI
(+)-2-Amino-2-deoxy-D-glucopyranose	HMDB
(3R,4R,5S,6R)-3-Amino-6-(hydroxymethyl)oxane-2,4,5-triol	HMDB
2-Amino-2-deoxy-D-glucopyranose	HMDB
2-Amino-2-deoxyglucose	HMDB
2-Aminoglucose	HMDB
2-Deoxy-2-amino-D-glucose	HMDB
2-Deoxy-2-aminoglucose	HMDB
Cosamin	HMDB
D-(+)-Glucosamine	HMDB
Dona	HMDB
Fides ecopharma brand OF glucosamine sulfate	HMDB
Rottapharm brand OF glucosamine sulfate	HMDB
Xicil	HMDB
2 Amino 2 deoxyglucose	HMDB
Glucosamine sulfate	HMDB
Sulfate, glucosamine	HMDB
Dona S	HMDB
Opfermann brand OF glucosamine sulfate	HMDB
Hespercorbin	HMDB

Molecular Formula

C₆H₁₃NO₅

Average Mass

179.1711

Monoisotopic Mass

179.079372531

IUPAC Name

(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol

Traditional Name

glucosamine

CAS Registry Number

3416-24-8

SMILES

N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O

InChI Identifier

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

InChI Key

MSWZFWKMSRAUBD-IVMDWMLBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Hexoses

Alternative Parents

Substituents

Hexose monosaccharide
Amino saccharide
Oxane
1,2-aminoalcohol
Hemiacetal
Secondary alcohol
Polyol
Organoheterocyclic compound
Oxacycle
Primary amine
Primary alcohol
Organopnictogen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Alcohol
Amine
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

D-glucosamine (CHEBI:47977 )
Amino sugars (C00329 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	551 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-3	ChemAxon
logS	0.49	ALOGPS
pKa (Strongest Acidic)	11.73	ChemAxon
pKa (Strongest Basic)	8.23	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	116.17 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	37.58 m³·mol⁻¹	ChemAxon
Polarizability	16.87 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Cartilage
Epidermis
Feces
Fibroblasts
Intestine
Platelet
Saliva
Urine

Tissue Locations

Cartilage
Epidermis
Fibroblasts
Intestine
Platelet

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191880	Glucokinase	Enzyme	P35557	Homo sapiens
MMDBp0191882	Hexokinase-3	Enzyme	P52790	Homo sapiens
MMDBp0191883	Hexokinase-2	Enzyme	P52789	Homo sapiens
MMDBp0191885	Hexokinase-1	Enzyme	P19367	Homo sapiens
MMDBp0193140	N-sulphoglucosamine sulphohydrolase	Unknown	P51688	Homo sapiens
MMDBp0193406	Tumor necrosis factor	Enzyme	P01375	Homo sapiens
MMDBp0194148	Di-N-acetylchitobiase	Enzyme	Q01459	Homo sapiens
MMDBp0196216	Peptide-N(4)-(N-acetyl-beta-glucosaminyl)asparagine amidase	Enzyme	Q96IV0	Homo sapiens
MMDBp0196842	Putative hexokinase HKDC1	Unknown	Q2TB90

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0019251	N'-monoacetylchitobiose-6'-phosphate	Glucosamine	6-phospho-beta-glucosidase	Carbohydrate hydrolysis	PathBank	31602464

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
Bacteria/Eubacteria	Actinobacteria	99	Human feces; Human stool; Human ; Human saliva; Human mucosa; Human supragingival plaque; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human subgingival plaque	Microbial culture; Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	116	Human stool; Human ; Human feces; Human urine; Human appendix biopsy; Human gastric fluid; Human saliva; Human subgingival plaque; Human supragingival plaque	Microbial culture; Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	5	Human feces; Human saliva; Human supragingival plaque	Microbial culture; Unknown
Bacteria/Eubacteria	Firmicutes	287	Human stool; Human ; Human feces; Human urine; Pig ; Cattle ; Human subgingival plaque	Microbial culture; Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	170	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human subgingival plaque	Microbial culture; Metabolic reconstruction
Eukaryota	Euglenozoa	1		Microbial culture
Bacteria	Actinobacteria	10	Human feces; Human stool; Human ; Human saliva; Human mucosa; Human supragingival plaque; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human subgingival plaque	Microbial culture; Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	3	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	8	Human feces; Human	Metabolic reconstruction
Bacteria	Proteobacteria	11	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human subgingival plaque	Microbial culture; Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	18	Human stool; Human ; Human feces; Human urine; Pig ; Cattle ; Human subgingival plaque	Microbial culture; Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	3	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea/Archaea	Euryarchaeota	5
Archaea/Archaea	nah	1

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB
Human Urine	Detected and Quantified	1.45				umol/mmol creatinine	Adult (>18 years old)	Both	Normal	HMDB	19309105
Human Blood	Detected and Quantified	0.29		0.0	0.6	uM	Adult (>18 years old)	Both	Normal	HMDB	17353133
Human Saliva	Detected and Quantified	3.02	4.13			uM	Adult (>18 years old)	Male	Normal	HMDB	Sugimoto et al. (2013) Physiological and environmental parameters associated with mass spectrometry-based salivary metabolomic profiles.
Human Cartilage	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Intestine	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Platelet	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Urine	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified						Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0001514

DrugBank ID

DB01296

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022668

KNApSAcK ID

Not Available

Chemspider ID

388352

KEGG Compound ID

C00329

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

47977

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Cheung HS, Nicoloff JT, Kamiel MB, Spolter L, Nimni ME: Stimulation of fibroblast biosynthetic activity by serum of patients with pretibial myxedema. J Invest Dermatol. 1978 Jul;71(1):12-7. doi: 10.1111/1523-1747.ep12543646. [PubMed:355562 ]
Rhodes M, Allen A, Dowling RH, Murphy G, Lennard TW: Inhibition of human gall bladder mucus synthesis in patients undergoing cholecystectomy. Gut. 1992 Aug;33(8):1113-7. doi: 10.1136/gut.33.8.1113. [PubMed:1398238 ]
Cope GF, Heatley RV, Kelleher J, Axon AT: In vitro mucus glycoprotein production by colonic tissue from patients with ulcerative colitis. Gut. 1988 Feb;29(2):229-34. doi: 10.1136/gut.29.2.229. [PubMed:3345934 ]
Ruoslahti E, Engvall E, Hayman EG, Spiro RG: Comparative studies on amniotic fluid and plasma fibronectins. Biochem J. 1981 Jan 1;193(1):295-9. doi: 10.1042/bj1930295. [PubMed:7305927 ]
Morita H, Kettlewell MG, Jewell DP, Kent PW: Glycosylation and sulphation of colonic mucus glycoproteins in patients with ulcerative colitis and in healthy subjects. Gut. 1993 Jul;34(7):926-32. doi: 10.1136/gut.34.7.926. [PubMed:8344580 ]
McCarty MF: Glucosamine may retard atherogenesis by promoting endothelial production of heparan sulfate proteoglycans. Med Hypotheses. 1997 Mar;48(3):245-51. doi: 10.1016/s0306-9877(97)90328-5. [PubMed:9140889 ]
McCarty MF: Enhanced synovial production of hyaluronic acid may explain rapid clinical response to high-dose glucosamine in osteoarthritis. Med Hypotheses. 1998 Jun;50(6):507-10. doi: 10.1016/s0306-9877(98)90272-9. [PubMed:9710325 ]
Hoffer LJ, Kaplan LN, Hamadeh MJ, Grigoriu AC, Baron M: Sulfate could mediate the therapeutic effect of glucosamine sulfate. Metabolism. 2001 Jul;50(7):767-70. doi: 10.1053/meta.2001.24201. [PubMed:11436179 ]
Roseman S: Reflections on glycobiology. J Biol Chem. 2001 Nov 9;276(45):41527-42. doi: 10.1074/jbc.R100053200. Epub 2001 Sep 11. [PubMed:11553646 ]
GHOSH S, BLUMENTHAL HJ, DAVIDSON E, ROSEMAN S: Glucosamine metabolism. V. Enzymatic synthesis of glucosamine 6-phosphate. J Biol Chem. 1960 May;235:1265-73. [PubMed:13827775 ]
Thatte HS, Zagarins S, Khuri SF, Fischer TH: Mechanisms of poly-N-acetyl glucosamine polymer-mediated hemostasis: platelet interactions. J Trauma. 2004 Jul;57(1 Suppl):S13-21. doi: 10.1097/01.ta.0000136743.12440.89. [PubMed:15280745 ]
Valeri CR, Srey R, Tilahun D, Ragno G: In vitro effects of poly-N-acetyl glucosamine on the activation of platelets in platelet-rich plasma with and without red blood cells. J Trauma. 2004 Jul;57(1 Suppl):S22-5; discussion S25. doi: 10.1097/01.ta.0000136744.12440.47. [PubMed:15280746 ]
Laverty S, Sandy JD, Celeste C, Vachon P, Marier JF, Plaas AH: Synovial fluid levels and serum pharmacokinetics in a large animal model following treatment with oral glucosamine at clinically relevant doses. Arthritis Rheum. 2005 Jan;52(1):181-91. doi: 10.1002/art.20762. [PubMed:15641100 ]
Towheed TE, Maxwell L, Anastassiades TP, Shea B, Houpt J, Robinson V, Hochberg MC, Wells G: Glucosamine therapy for treating osteoarthritis. Cochrane Database Syst Rev. 2005 Apr 18;(2):CD002946. doi: 10.1002/14651858.CD002946.pub2. [PubMed:15846645 ]
Cibere J, Thorne A, Kopec JA, Singer J, Canvin J, Robinson DB, Pope J, Hong P, Grant E, Lobanok T, Ionescu M, Poole AR, Esdaile JM: Glucosamine sulfate and cartilage type II collagen degradation in patients with knee osteoarthritis: randomized discontinuation trial results employing biomarkers. J Rheumatol. 2005 May;32(5):896-902. [PubMed:15868627 ]
Biggee BA, Blinn CM, McAlindon TE, Nuite M, Silbert JE: Low levels of human serum glucosamine after ingestion of glucosamine sulphate relative to capability for peripheral effectiveness. Ann Rheum Dis. 2006 Feb;65(2):222-6. doi: 10.1136/ard.2005.036368. Epub 2005 Aug 3. [PubMed:16079170 ]
Huang TM, Cai L, Yang B, Zhou MX, Shen YF, Duan GL: Liquid chromatography with electrospray ionization mass spectrometry method for the assay of glucosamine sulfate in human plasma: validation and application to a pharmacokinetic study. Biomed Chromatogr. 2006 Mar;20(3):251-6. doi: 10.1002/bmc.558. [PubMed:16145658 ]
Uitterlinden EJ, Jahr H, Koevoet JL, Jenniskens YM, Bierma-Zeinstra SM, Degroot J, Verhaar JA, Weinans H, van Osch GJ: Glucosamine decreases expression of anabolic and catabolic genes in human osteoarthritic cartilage explants. Osteoarthritis Cartilage. 2006 Mar;14(3):250-7. doi: 10.1016/j.joca.2005.10.001. Epub 2005 Nov 18. [PubMed:16300972 ]
Buse MG: Hexosamines, insulin resistance, and the complications of diabetes: current status. Am J Physiol Endocrinol Metab. 2006 Jan;290(1):E1-E8. doi: 10.1152/ajpendo.00329.2005. [PubMed:16339923 ]
Zhang LJ, Huang TM, Fang XL, Li XN, Wang QS, Zhang ZW, Sha XY: Determination of glucosamine sulfate in human plasma by precolumn derivatization using high performance liquid chromatography with fluorescence detection: its application to a bioequivalence study. J Chromatogr B Analyt Technol Biomed Life Sci. 2006 Sep 14;842(1):8-12. doi: 10.1016/j.jchromb.2006.04.045. Epub 2006 Jun 5. [PubMed:16740419 ]

Showing metabocard for Glucosamine (MMDBc0000199)

MOL for #<Metabolite:0x00007f920e7c3448>

3D MOL for #<Metabolite:0x00007f920e7c3448>

3D SDF for #<Metabolite:0x00007f920e7c3448>

3D-SDF for #<Metabolite:0x00007f920e7c3448>

PDB for #<Metabolite:0x00007f920e7c3448>

3D PDB for #<Metabolite:0x00007f920e7c3448>

SMILES for #<Metabolite:0x00007f920e7c3448>

INCHI for #<Metabolite:0x00007f920e7c3448>

Structure for #<Metabolite:0x00007f920e7c3448>

3D Structure for #<Metabolite:0x00007f920e7c3448>