MiMeDB: Showing metabocard for Glucosamine (MMDBc0000199)

Microbial

Record Information

Version

2.0

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

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-06tr-9300000000-7e2a89f48724cdda814c	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0ul9-9847700000-b4779809586433e7ec78	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-4900000000-364d52fc6e7e423f52bb	2018-05-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-762e016c89a40a9e3f49	2018-05-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9000000000-bd04d561d78f2abad229	2018-05-25	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9500000000-9bfc2897a4b66f71c7a1	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9000000000-f842b779439be8970cd9	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-074i-9000000000-622ec0743231c0cbaca6	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-9700000000-5087af92679b2640ba6c	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-b9ba212915cbdaed8628	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-2d1825b518f09745e036	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03la-9100000000-3da7ee17d7512a59e3ef	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-9400000000-cca17ef05a47a7be4d43	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01x0-9500000000-5fbd02d318d3ec58f98b	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0abc-9000000000-11e86d324c183174364e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-001i-0900000000-3ba18bb57823024db64e	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-9500000000-52f44695a6cfb6459105	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9800000000-264ee54a99e01e0d4e30	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9000000000-08f87dc3e44979542ca2	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-06r6-9000000000-635fa893be82ffdeca97	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-03e9-9600000000-09232c8766303805f765	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0900000000-4c88765919efa0ec2d2d	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ea-6900000000-301590fbe90692448d5e	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052g-9100000000-d6a51790ce1df14a067a	2016-08-02	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-9400000000-e43a7a5cb44f6c461544	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-053r-9800000000-56b95ef43b164db5524d	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-1434c5ce1e9649c1cbf1	2016-08-03	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-25	View Spectrum
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)		2018-05-25	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2018-05-25	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (eluted)	2025-10-23	517.6
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	409.8
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (void)	2025-10-23	43.0
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	223.8
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	296.9
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (void)	2025-10-23	299.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	434.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	912.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	777.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	176.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	601.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (void)	2025-10-23	186.9
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	27.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	384.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	790.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	82.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-23	325.1
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	648.0
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	549.9

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	Glucosamine_TMS_1	C[Si](C)(C)OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1N	standard non polar	2025-10-23	1871.98
Gas Chromatography	Glucosamine_TMS_2	C[Si](C)(C)OC[C@H]1OC(O)[C@H](N)[C@@H](O)[C@@H]1O	standard non polar	2025-10-23	1739.15
Gas Chromatography	Glucosamine_TMS_3	C[Si](C)(C)O[C@@H]1[C@@H](CO)OC(O)[C@H](N)[C@H]1O	standard non polar	2025-10-23	1680.91
Gas Chromatography	Glucosamine_TMS_4	C[Si](C)(C)O[C@@H]1[C@@H](N)C(O)O[C@H](CO)[C@H]1O	standard non polar	2025-10-23	1693.8
Gas Chromatography	Glucosamine_TMS_5	C[Si](C)(C)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O	standard non polar	2025-10-23	2008.95
Gas Chromatography	Glucosamine_TMS_6	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](N)[C@@H](O)[C@@H]1O	standard non polar	2025-10-23	1908.67
Gas Chromatography	Glucosamine_TMS_7	C[Si](C)(C)OC1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1N	standard non polar	2025-10-23	2151.09
Gas Chromatography	Glucosamine_TMS_8	C[Si](C)(C)OC1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1N	standard non polar	2025-10-23	1899.67
Gas Chromatography	Glucosamine_TMS_9	C[Si](C)(C)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O	standard non polar	2025-10-23	1642.01
Gas Chromatography	Glucosamine_TMS_10	C[Si](C)(C)OC[C@H]1OC(O)[C@H](N)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard non polar	2025-10-23	2105.83
Gas Chromatography	Glucosamine_TMS_11	C[Si](C)(C)OC[C@H]1OC(O)[C@H](N)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	2245.06
Gas Chromatography	Glucosamine_TMS_12	C[Si](C)(C)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O	standard non polar	2025-10-23	2089.49
Gas Chromatography	Glucosamine_TMS_13	C[Si](C)(C)O[C@@H]1[C@@H](CO)OC(O)[C@H](N)[C@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1864.1
Gas Chromatography	Glucosamine_TMS_14	C[Si](C)(C)N[C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard non polar	2025-10-23	1498.06
Gas Chromatography	Glucosamine_TMS_15	C[Si](C)(C)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	2118.17
Gas Chromatography	Glucosamine_TMS_16	C[Si](C)(C)N([C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C	standard non polar	2025-10-23	1882.68
Gas Chromatography	Glucosamine_TMS_17	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](N)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard non polar	2025-10-23	2358.39
Gas Chromatography	Glucosamine_TMS_18	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](N)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1440.27
Gas Chromatography	Glucosamine_TMS_19	C[Si](C)(C)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O	standard non polar	2025-10-23	2023.52
Gas Chromatography	Glucosamine_TMS_20	C[Si](C)(C)OC1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1N	standard non polar	2025-10-23	1633.06
Gas Chromatography	Glucosamine_TMS_21	C[Si](C)(C)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard non polar	2025-10-23	1630.84
Gas Chromatography	Glucosamine_TMS_22	C[Si](C)(C)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1800.26
Gas Chromatography	Glucosamine_TMS_23	C[Si](C)(C)OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	2039.9
Gas Chromatography	Glucosamine_TMS_24	C[Si](C)(C)OC[C@H]1OC(O)[C@H](N)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1774.83
Gas Chromatography	Glucosamine_TMS_25	C[Si](C)(C)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	2515.13
Gas Chromatography	Glucosamine_TMS_26	C[Si](C)(C)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard non polar	2025-10-23	1456.23
Gas Chromatography	Glucosamine_TMS_27	C[Si](C)(C)OC[C@H]1OC(O)[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@@H]1O	standard non polar	2025-10-23	1668.34
Gas Chromatography	Glucosamine_TMS_28	C[Si](C)(C)N[C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1722.42
Gas Chromatography	Glucosamine_TMS_29	C[Si](C)(C)O[C@@H]1[C@@H](CO)OC(O)[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H]1O	standard non polar	2025-10-23	1474.97
Gas Chromatography	Glucosamine_TMS_30	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)OC(O)[C@@H]1N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	2247.06
Gas Chromatography	Glucosamine_TMS_31	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](N)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	2252.96
Gas Chromatography	Glucosamine_TMS_32	C[Si](C)(C)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1679.19
Gas Chromatography	Glucosamine_TMS_33	C[Si](C)(C)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard non polar	2025-10-23	2633.13
Gas Chromatography	Glucosamine_TMS_34	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@@H]1O	standard non polar	2025-10-23	1427.48
Gas Chromatography	Glucosamine_TMS_35	C[Si](C)(C)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	2172.49
Gas Chromatography	Glucosamine_TMS_36	C[Si](C)(C)OC1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	1810.55
Gas Chromatography	Glucosamine_TMS_37	C[Si](C)(C)OC1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	2696.5
Gas Chromatography	Glucosamine_TMS_38	C[Si](C)(C)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	2133.09
Gas Chromatography	Glucosamine_TMS_39	C[Si](C)(C)OC[C@H]1OC(O)[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard non polar	2025-10-23	2366.21
Gas Chromatography	Glucosamine_TMS_40	C[Si](C)(C)OC[C@H]1OC(O)[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	2752.73
Gas Chromatography	Glucosamine_TMS_41	C[Si](C)(C)O[C@@H]1[C@@H](CO)OC(O)[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H]1O[Si](C)(C)C	standard non polar	2025-10-23	2426.04
Gas Chromatography	Glucosamine_TMS_42	C[Si](C)(C)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1724.41
Gas Chromatography	Glucosamine_TMS_43	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard non polar	2025-10-23	1998.23
Gas Chromatography	Glucosamine_TMS_44	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1596.53
Gas Chromatography	Glucosamine_TMS_45	C[Si](C)(C)OC1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1N([Si](C)(C)C)[Si](C)(C)C	standard non polar	2025-10-23	2343.61
Gas Chromatography	Glucosamine_TMS_46	C[Si](C)(C)OC[C@H]1OC(O)[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	1836.65
Gas Chromatography	Glucosamine_TMS_47	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard non polar	2025-10-23	2022.23
Gas Chromatography	Glucosamine_TMS_1	C[Si](C)(C)OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1N	standard polar	2025-10-23	2152.81
Gas Chromatography	Glucosamine_TMS_2	C[Si](C)(C)OC[C@H]1OC(O)[C@H](N)[C@@H](O)[C@@H]1O	standard polar	2025-10-23	1520.38
Gas Chromatography	Glucosamine_TMS_3	C[Si](C)(C)O[C@@H]1[C@@H](CO)OC(O)[C@H](N)[C@H]1O	standard polar	2025-10-23	2052.04
Gas Chromatography	Glucosamine_TMS_4	C[Si](C)(C)O[C@@H]1[C@@H](N)C(O)O[C@H](CO)[C@H]1O	standard polar	2025-10-23	2337.96
Gas Chromatography	Glucosamine_TMS_5	C[Si](C)(C)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O	standard polar	2025-10-23	1945.57
Gas Chromatography	Glucosamine_TMS_6	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](N)[C@@H](O)[C@@H]1O	standard polar	2025-10-23	2418.64
Gas Chromatography	Glucosamine_TMS_7	C[Si](C)(C)OC1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1N	standard polar	2025-10-23	2039.19
Gas Chromatography	Glucosamine_TMS_8	C[Si](C)(C)OC1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1N	standard polar	2025-10-23	1540.65
Gas Chromatography	Glucosamine_TMS_9	C[Si](C)(C)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O	standard polar	2025-10-23	1810.08
Gas Chromatography	Glucosamine_TMS_10	C[Si](C)(C)OC[C@H]1OC(O)[C@H](N)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard polar	2025-10-23	2098.33
Gas Chromatography	Glucosamine_TMS_11	C[Si](C)(C)OC[C@H]1OC(O)[C@H](N)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	2046.74
Gas Chromatography	Glucosamine_TMS_12	C[Si](C)(C)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O	standard polar	2025-10-23	2305.16
Gas Chromatography	Glucosamine_TMS_13	C[Si](C)(C)O[C@@H]1[C@@H](CO)OC(O)[C@H](N)[C@H]1O[Si](C)(C)C	standard polar	2025-10-23	2301.23
Gas Chromatography	Glucosamine_TMS_14	C[Si](C)(C)N[C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard polar	2025-10-23	1725.46
Gas Chromatography	Glucosamine_TMS_15	C[Si](C)(C)N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	1847.28
Gas Chromatography	Glucosamine_TMS_16	C[Si](C)(C)N([C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O)[Si](C)(C)C	standard polar	2025-10-23	1891.31
Gas Chromatography	Glucosamine_TMS_17	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](N)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard polar	2025-10-23	1885.72
Gas Chromatography	Glucosamine_TMS_18	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](N)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	2100.24
Gas Chromatography	Glucosamine_TMS_19	C[Si](C)(C)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O	standard polar	2025-10-23	1510.43
Gas Chromatography	Glucosamine_TMS_20	C[Si](C)(C)OC1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1N	standard polar	2025-10-23	2201.58
Gas Chromatography	Glucosamine_TMS_21	C[Si](C)(C)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard polar	2025-10-23	2318.85
Gas Chromatography	Glucosamine_TMS_22	C[Si](C)(C)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	2081.27
Gas Chromatography	Glucosamine_TMS_23	C[Si](C)(C)OC1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	1378.86
Gas Chromatography	Glucosamine_TMS_24	C[Si](C)(C)OC[C@H]1OC(O)[C@H](N)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	1344.34
Gas Chromatography	Glucosamine_TMS_25	C[Si](C)(C)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	2233.95
Gas Chromatography	Glucosamine_TMS_26	C[Si](C)(C)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard polar	2025-10-23	1507.74
Gas Chromatography	Glucosamine_TMS_27	C[Si](C)(C)OC[C@H]1OC(O)[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@@H]1O	standard polar	2025-10-23	2338.31
Gas Chromatography	Glucosamine_TMS_28	C[Si](C)(C)N[C@H]1C(O)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	1838.62
Gas Chromatography	Glucosamine_TMS_29	C[Si](C)(C)O[C@@H]1[C@@H](CO)OC(O)[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H]1O	standard polar	2025-10-23	1411.63
Gas Chromatography	Glucosamine_TMS_30	C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](CO)OC(O)[C@@H]1N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	1929.93
Gas Chromatography	Glucosamine_TMS_31	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](N)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	3025.36
Gas Chromatography	Glucosamine_TMS_32	C[Si](C)(C)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	1911.15
Gas Chromatography	Glucosamine_TMS_33	C[Si](C)(C)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard polar	2025-10-23	2060.71
Gas Chromatography	Glucosamine_TMS_34	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@@H]1O	standard polar	2025-10-23	2185.28
Gas Chromatography	Glucosamine_TMS_35	C[Si](C)(C)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	2087.69
Gas Chromatography	Glucosamine_TMS_36	C[Si](C)(C)OC1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O)[C@H]1N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2314.68
Gas Chromatography	Glucosamine_TMS_37	C[Si](C)(C)OC1O[C@H](CO)[C@@H](O)[C@H](O[Si](C)(C)C)[C@H]1N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	1193.52
Gas Chromatography	Glucosamine_TMS_38	C[Si](C)(C)N[C@H]1C(O)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	2193.13
Gas Chromatography	Glucosamine_TMS_39	C[Si](C)(C)OC[C@H]1OC(O)[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard polar	2025-10-23	2169.28
Gas Chromatography	Glucosamine_TMS_40	C[Si](C)(C)OC[C@H]1OC(O)[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	1926.55
Gas Chromatography	Glucosamine_TMS_41	C[Si](C)(C)O[C@@H]1[C@@H](CO)OC(O)[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@H]1O[Si](C)(C)C	standard polar	2025-10-23	2619.01
Gas Chromatography	Glucosamine_TMS_42	C[Si](C)(C)N[C@H]1C(O[Si](C)(C)C)O[C@H](CO[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	3195.76
Gas Chromatography	Glucosamine_TMS_43	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O	standard polar	2025-10-23	1884.88
Gas Chromatography	Glucosamine_TMS_44	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	2786.86
Gas Chromatography	Glucosamine_TMS_45	C[Si](C)(C)OC1O[C@H](CO)[C@@H](O[Si](C)(C)C)[C@H](O[Si](C)(C)C)[C@H]1N([Si](C)(C)C)[Si](C)(C)C	standard polar	2025-10-23	2354.27
Gas Chromatography	Glucosamine_TMS_46	C[Si](C)(C)OC[C@H]1OC(O)[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	2213.23
Gas Chromatography	Glucosamine_TMS_47	C[Si](C)(C)OC[C@H]1OC(O[Si](C)(C)C)[C@H](N([Si](C)(C)C)[Si](C)(C)C)[C@@H](O[Si](C)(C)C)[C@@H]1O[Si](C)(C)C	standard polar	2025-10-23	2192.56

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

Microbial Pathways

Pathways

Name	SMPDB/PathBank	Species
Chitobiose Degradation		Escherichia coli Escherichia coli SMS-3-5 Escherichia coli UTI89 Escherichia coli 55989 Escherichia coli SE11 Acinetobacter sp. ADP1 Escherichia coli CFT073 Myxococcus xanthus DK 1622 Klebsiella pneumoniae Bacillus cereus Pseudomonas fluorescens Pf-5 Clostridium saccharoperbutylacetonicum N1-4(HMT) Salmonella enterica Acidaminococcus fermentans DSM 20731 Acidaminococcus intestini RyC-MR95 Acinetobacter baumannii Anaerostipes caccae Anaerostipes hadrus Bacillus cereus AH187 (F4810/72) Bacillus halodurans C-125 Bacteroides cellulosilyticus Blautia obeum ATCC 29174 Brevibacillus brevis NBRC 100599 Clostridium beijerinckii NCIMB 8052 Enterococcus faecalis Geobacter metallireducens Methylobacterium nodulans Parabacteroides distasonis Parabacteroides distasonis ATCC 8503 Burkholderia cepacia Bradyrhizobium japonicum Mesorhizobium loti Acidiphilium cryptum Chromobacterium violaceum Citrobacter koseri Proteus mirabilis Shigella boydii Shigella sonnei Vibrio vulnificus Bacteroides uniformis Syntrophomonas wolfei Desulfovibrio salexigens Acidithiobacillus ferrooxidans Cytophaga hutchinsonii Rhodopseudomonas palustris Streptococcus equinus Enterococcus gallinarum Bacillus licheniformis Bacillus mycoides Bacillus thuringiensis Clostridium butyricum Lactobacillus plantarum Lactobacillus sakei Listeria monocytogenes Pelobacter propionicus Enterococcus avium Veillonella atypica Veillonella dispar Enterococcus cecorum Mitsuokella multacida Burkholderia vietnamiensis Holdemania filiformis Enterobacter cancerogenus Bacillus clausii Bacillus selenitireducens Achromobacter xylosoxidans Burkholderia multivorans Burkholderia cenocepacia Syntrophobacter fumaroxidans Citrobacter youngae Collinsella stercoris Burkholderia ambifaria Ilyobacter polytropus Alicycliphilus denitrificans Desulfovibrio magneticus Methylocella silvestris Escherichia albertii Dialister invisus Geobacter bemidjiensis Geobacter lovleyi Streptococcus gallolyticus Bacteroides intestinalis Bacteroides oleiciplenus Blautia obeum Clostridium beijerinckii Enterococcus faecium Klebsiella variicola Lactobacillus rhamnosus Veillonella parvula Achromobacter xylosoxidans A8 Acinetobacter baumannii SDF Acinetobacter baumannii ACICU Acinetobacter baumannii AB0057 Acinetobacter baumannii AB307-0294 Bacillus cereus ATCC 10987 Bacillus thuringiensis serovar konkukian str. 97-27 Bacillus licheniformis ATCC 14580 Bacillus clausii KSM-K16 Bacillus cereus B4264 Bacillus cereus AH820 Bacillus cereus G9842 Bacillus cereus Q1 Bradyrhizobium japonicum USDA 110 Citrobacter koseri ATCC BAA-895 Dyadobacter fermentans DSM 18053 Enterobacter cloacae subsp. cloacae ATCC 13047 Escherichia coli APEC O1 Escherichia coli E24377A Escherichia coli O127:H6 str. E2348/69 Escherichia coli UMN026 Escherichia fergusonii ATCC 35469 Escherichia coli ED1a Escherichia coli IAI39 Klebsiella pneumoniae subsp. pneumoniae MGH 78578 Lactobacillus plantarum WCFS1 Lactobacillus acidophilus NCFM Lactobacillus sakei subsp. sakei 23K Laribacter hongkongensis HLHK9 Mesorhizobium loti MAFF303099 Methylobacterium radiotolerans JCM 2831 Methylobacterium populi BJ001 Escherichia coli 042 Pediococcus pentosaceus ATCC 25745 Proteus mirabilis HI4320 Pseudomonas fluorescens Pf0-1 Salmonella enterica subsp. enterica serovar Typhimurium str. LT2 Salmonella enterica subsp. enterica serovar Newport str. SL254 Salmonella enterica subsp. enterica serovar Heidelberg str. SL476 Salmonella enterica subsp. enterica serovar Agona str. SL483 Salmonella enterica subsp. enterica serovar Dublin str. CT02021853 Shigella sonnei Ss046 Shigella flexneri 5 str. 8401 Spirosoma linguale DSM 74 Vibrio parahaemolyticus RIMD 2210633 Yersinia enterocolitica subsp. enterocolitica 8081 Yersinia pseudotuberculosis IP 31758 Bacteroides cellulosilyticus DSM 14838 Bacteroides intestinalis DSM 17393 Bacteroides oleiciplenus YIT 12058 Bacteroides uniformis ATCC 8492 Bacteroides sp. D20 Parabacteroides sp. D13 Spirosoma linguale Beijerinckia indica Bradyrhizobium elkanii Methylobacterium mesophilicum Methylobacterium mesophilicum SR1.6/6 Azorhizobium caulinodans Xanthobacter autotrophicus Alcaligenes faecalis Burkholderia cepacia GG4 Cedecea davisae Cedecea davisae DSM 4568 Citrobacter amalonaticus Citrobacter amalonaticus Y19 Citrobacter freundii Citrobacter youngae ATCC 29220 Enterobacter hormaechei Escherichia albertii TW07627 Klebsiella aerogenes Salmonella Salmonella enterica subsp. enterica serovar Typhimurium Trabulsiella guamensis Trabulsiella guamensis ATCC 49490 Hafnia alvei Providencia stuartii ATCC 25827 Serratia marcescens subsp. marcescens Db11 Yersinia enterocolitica Yersinia pestis Yersinia pseudotuberculosis Legionella pneumophila Francisella tularensis Vibrio parahaemolyticus Vibrio mimicus Collinsella stercoris DSM 13279 Bacillus infantis NRRL B-14911 Listeria grayi Listeria grayi DSM 20601 Listeria monocytogenes 10403S Enterococcus asini ATCC 700915 Enterococcus cecorum DSM 20682 = ATCC 43198 Enterococcus dispar ATCC 51266 Enterococcus phoeniculicola ATCC BAA-412 Lactobacillus rhamnosus LMS2-1 Lactobacillus mucosae LM1 Pediococcus pentosaceus Lactococcus garvieae Butyricicoccus pullicaecorum Butyricicoccus pullicaecorum 1.2 Clostridium butyricum E4 str. BoNT E BL5262 Clostridium celatum DSM 1785 Clostridium sartagoforme AAU1 Anaerostipes caccae DSM 14662 Clostridium asparagiforme DSM 15981 Eggerthia catenaformis OT 569 = DSM 20559 [Clostridium] innocuum 2959 Holdemania filiformis DSM 12042 Kandleria vitulina Kandleria vitulina DSM 20405 Acidaminococcus intestini Phascolarctobacterium succinatutens YIT 12067 Mitsuokella multacida DSM 20544 Dialister invisus DSM 15470 Dialister succinatiphilus Dialister succinatiphilus YIT 11850 Megasphaera elsdenii Veillonella atypica ACS-049-V-Sch6 Veillonella dispar ATCC 17748 Bordetella pertussis Tohama I Bordetella parapertussis 12822 Ralstonia eutropha H16 Vibrio cholerae M66-2 Vibrio cholerae O1 biovar El Tor str. N16961 Clostridioides difficile 630 Clostridioides difficile NAP08 Bacillus cytotoxicus NVH 391-98 Streptococcus pasteurianus ATCC 43144 Alkaliphilus metalliredigens QYMF Bacillus selenitireducens MLS10 Beutenbergia cavernae DSM 12333 Candidatus Desulforudis audaxviator MP104C Exiguobacterium sp. AT1b Geobacillus thermodenitrificans NG80-2 Lactobacillus crispatus ST1 Listeria innocua Clip11262 Listeria welshimeri serovar 6b str. SLCC5334 Nakamurella multipartita DSM 44233 Oceanobacillus iheyensis HTE831 Thermobaculum terrenum ATCC BAA-798 Streptococcus gallolyticus UCN34 Streptomyces violaceusniger Tu 4113 Symbiobacterium thermophilum IAM 14863 Thermoanaerobacter sp. X514 Thermoanaerobacter pseudethanolicus ATCC 33223 Paraburkholderia graminis C4D1M Acidipropionibacterium acidipropionici ATCC 4875 Holdemanella biformis DSM 3989 Klebsiella aerogenes KCTC 2190 Acaryochloris marina MBIC11017 Acidiphilium cryptum JF-5 Acidiphilium multivorum AIU301 Acidithiobacillus ferrooxidans ATCC 23270 Acidobacterium capsulatum ATCC 51196 Agrobacterium vitis S4 Alicycliphilus denitrificans K601 Vibrio fischeri MJ11 Aliivibrio salmonicida LFI1238 Anaeromyxobacter dehalogenans 2CP-C Anaeromyxobacter sp. Fw109-5 Anaeromyxobacter sp. K Anaeromyxobacter dehalogenans 2CP-1 Azorhizobium caulinodans ORS 571 Azotobacter vinelandii DJ Beijerinckia indica subsp. indica ATCC 9039 Bordetella petrii DSM 12804 Bradyrhizobium sp. ORS278 Bradyrhizobium sp. BTAi1 Brucella melitensis bv. 1 str. 16M Brucella abortus bv. 1 str. 9-941 Brucella ovis ATCC 25840 Brucella canis ATCC 23365 Brucella suis ATCC 23445 Brucella abortus S19 Brucella melitensis ATCC 23457 Brucella microti CCM 4915 Burkholderia mallei ATCC 23344 Burkholderia pseudomallei 1710b Burkholderia sp. 383 Burkholderia xenovorans LB400 Burkholderia ambifaria AMMD Burkholderia mallei NCTC 10229 Burkholderia pseudomallei 1106a Burkholderia vietnamiensis G4 Burkholderia cenocepacia MC0-3 Burkholderia ambifaria MC40-6 Burkholderia phymatum STM815 Burkholderia phytofirmans PsJN Burkholderia cenocepacia J2315 Burkholderia rhizoxinica HKI 454 Candidatus Koribacter versatilis Ellin345 Chloroflexus aurantiacus J-10-fl Chloroflexus aggregans DSM 9485 Citrobacter rodentium ICC168 Cupriavidus metallidurans CH34 Cupriavidus taiwanensis LMG 19424 Cupriavidus necator N-1 Cytophaga hutchinsonii ATCC 33406 Desulfovibrio magneticus RS-1 Desulfovibrio salexigens DSM 2638 Enterobacter sp. 638 Enterobacter cloacae SCF1 Francisella tularensis subsp. holarctica LVS Geobacter metallireducens GS-15 Geobacter uraniireducens Rf4 Geobacter lovleyi SZ Geobacter bemidjiensis Bem Geobacter sp. FRC-32 Geobacter sp. M18 Gluconacetobacter diazotrophicus PAl 5 Gluconobacter oxydans 621H Granulibacter bethesdensis CGDNIH1 Halothiobacillus neapolitanus c2 Herminiimonas arsenicoxydans Ilyobacter polytropus DSM 2926 Janthinobacterium sp. Marseille Klebsiella pneumoniae 342 Leadbetterella byssophila DSM 17132 Legionella pneumophila subsp. pneumophila str. Philadelphia 1 Legionella pneumophila str. Lens Legionella longbeachae NSW150 Magnetospirillum magneticum AMB-1 Methylobacterium chloromethanicum CM4 Methylobacterium nodulans ORS 2060 Methylobacterium extorquens AM1 Methylobacterium extorquens DM4 Methylocella silvestris BL2 Methylotenera mobilis JLW8 Methylovorus glucosetrophus SIP3-4 Nitrobacter winogradskyi Nb-255 Nitrobacter hamburgensis X14 Geobacter sulfurreducens PCA Chromobacterium violaceum ATCC 12472 Syntrophomonas wolfei subsp. wolfei str. Goettingen Pelobacter propionicus DSM 2379 Photobacterium profundum SS9 Prochlorococcus marinus str. MIT 9313 Prochlorococcus marinus str. MIT 9303 Rhodopseudomonas palustris CGA009 Rhodopseudomonas palustris HaA2 Rhodopseudomonas palustris BisB5 Rhodospirillum centenum SW Rhodothermus marinus DSM 4252 Salmonella enterica subsp. enterica serovar Paratyphi A str. Sebaldella termitidis ATCC 33386 Shigella flexneri 2a str. 301 Synechococcus sp. WH 8102 Synechococcus sp. CC9902 Synechococcus sp. WH 7803 Synechococcus sp. RCC307 Syntrophobacter fumaroxidans MPOB Teredinibacter turnerae T7901 Vibrio vulnificus CMCP6 Vibrio vulnificus YJ016 Xanthobacter autotrophicus Py2 Zymomonas mobilis subsp. pomaceae ATCC 29192 Klebsiella michiganensis KCTC 1686 Veillonella seminalis ACS-216-V-Col6b Veillonella sp. 6_1_27

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated 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	108	Human feces; 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 feces; Human ; 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	305	Human feces; Human ; Human urine; Pig ; Cattle ; Human subgingival plaque	Microbial culture; Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	180	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/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/Eubacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Tenericutes	3	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Bacteria	Actinobacteria	1	Human feces; 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
Archaea/Archaea	Euryarchaeota	5
Archaea/Archaea	nah	1
Bacteria	Proteobacteria	1	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

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

CMMC Knowledgebase

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:0x00007f9ab402a098>

3D MOL for #<Metabolite:0x00007f9ab402a098>

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Structure for #<Metabolite:0x00007f9ab402a098>

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