NP-MRD: Showing NP-Card for Glucosamine (NP0000355)

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Record Information

Version

2.0

Created at

2005-11-16 15:48:42 UTC

Updated at

2024-09-17 15:41:45 UTC

NP-MRD ID

NP0000355

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Glucosamine

Description

Glucosamine (C6H13NO5) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. Glucosamine is part of the structure of two polysaccharides, chitosan and chitin. Glucosamine is one of the most abundant monosaccharides. Produced commercially by the hydrolysis of shellfish exoskeletons or, less commonly, by fermentation of a grain such as corn or wheat, glucosamine has many names depending on country. Although a common dietary supplement, there is little evidence that it is effective for relief of arthritis or pain, and is not an approved prescription drug. 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. 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. Its use as a therapy for osteoarthritis appears safe but there is conflicting evidence as to its effectiveness. Glucosamine is naturally present in the shells of shellfish, animal bones, bone marrow, and fungi. D-Glucosamine is made naturally in the form of glucosamine-6-phosphate, and is the biochemical precursor of all nitrogen-containing sugars. Specifically in humans, glucosamine-6-phosphate is synthesized from fructose 6-phosphate and glutamine by glutamine—fructose-6-phosphate transaminase as the first step of the hexosamine biosynthesis pathway. The end-product of this pathway is uridine diphosphate N-acetylglucosamine (UDP-GlcNAc), which is then used for making glycosaminoglycans, proteoglycans, and glycolipids. As the formation of glucosamine-6-phosphate is the first step for the synthesis of these products, glucosamine may be important in regulating their production; however, the way that the hexosamine biosynthesis pathway is actually regulated, and whether this could be involved in contributing to human disease remains unclear.

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

View in JSmol View NMR Assignments

Synonyms

Value	Source
2-Amino-2-deoxy-D-glucose	ChEBI
Chitosamine	ChEBI
D-Glucosamine	ChEBI
WURCS=2.0/1,1,0/[a2122h-1x_1-5_2*n]/1/	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

Chemical Formula

C₆H₁₃NO₅

Average Mass

179.1711 Da

Monoisotopic Mass

179.07937 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Cannabis sativa	CannabisDB	Not Available
Capra aegagrus hircus	FooDB	FooDB
Capsicum annuum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Daphnia pulex	LOTUS Database	35616633
Daucus carota ssp. sativus	FooDB	David M. Alabran, and Ahmed F. Mabrouk. Carrot flavor. Sugars and free nitrogenous compounds in f...
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Glycine max	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Juncus roemerianus	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Matricaria recutita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Mus musculus	LOTUS Database	35616633
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phaseolus vulgaris	KNApSAcK Database	22123792
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Ramalina fraxinea	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB
Trypanosoma brucei	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Aspergillus niger	KNApSAcK Database	22123792

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 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	88 °C	Not Available
Boiling Point	449.00 to 450.00 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	330 mg/mL	Not Available
LogP	-2.175 (est)	The Good Scents Company Information System

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

External Links

HMDB ID

HMDB0001514

DrugBank ID

DB01296

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

47977

Good Scents ID

rw1365631

References

General References

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. [PubMed:15280745 ]
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. [PubMed:7305927 ]
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. [PubMed:1398238 ]
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 ]
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. [PubMed:8344580 ]
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. Epub 2006 Jun 5. [PubMed:16740419 ]
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. [PubMed:11436179 ]
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. [PubMed:16145658 ]
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. Epub 2005 Aug 3. [PubMed:16079170 ]
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. [PubMed:9710325 ]
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. Epub 2005 Nov 18. [PubMed:16300972 ]
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. [PubMed:3345934 ]
McCarty MF: Glucosamine may retard atherogenesis by promoting endothelial production of heparan sulfate proteoglycans. Med Hypotheses. 1997 Mar;48(3):245-51. [PubMed:9140889 ]
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. [PubMed:355562 ]
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. [PubMed:15280746 ]
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 ]
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. [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. [PubMed:15846645 ]
Buse MG: Hexosamines, insulin resistance, and the complications of diabetes: current status. Am J Physiol Endocrinol Metab. 2006 Jan;290(1):E1-E8. [PubMed:16339923 ]

Showing NP-Card for Glucosamine (NP0000355)

MOL for NP0000355 (Glucosamine)

3D MOL for NP0000355 (Glucosamine)

3D SDF for NP0000355 (Glucosamine)

3D-SDF for NP0000355 (Glucosamine)

PDB for NP0000355 (Glucosamine)

3D PDB for NP0000355 (Glucosamine)

SMILES for NP0000355 (Glucosamine)

INCHI for NP0000355 (Glucosamine)

Structure for NP0000355 (Glucosamine)

3D Structure for NP0000355 (Glucosamine)