Livestock Metabolome Database: Showing metabocard for Glucosamine (LMDB00341)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:47:42 UTC

Update Date

2016-09-23 18:45:12 UTC

Lmdb

LMDB00341

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Glucosamine

Description

In the United States, glucosamine is not approved by the Food and Drug Administration for medical use in animals. 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 SDF PDB SMILES InChI

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

Chemical Formula

C₆H₁₃NO₅

Average Molecular Weight

179.1711

Monoisotopic Molecular Weight

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 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-06tr-9300000000-7e2a89f48724cdda814c	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-0ul9-9847700000-b4779809586433e7ec78	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-4900000000-364d52fc6e7e423f52bb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00di-9000000000-762e016c89a40a9e3f49	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00di-9000000000-bd04d561d78f2abad229	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9500000000-9bfc2897a4b66f71c7a1	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9000000000-f842b779439be8970cd9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-074i-9000000000-622ec0743231c0cbaca6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-9700000000-5087af92679b2640ba6c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-b9ba212915cbdaed8628	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-2d1825b518f09745e036	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-03la-9100000000-3da7ee17d7512a59e3ef	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-9400000000-cca17ef05a47a7be4d43	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-01x0-9500000000-5fbd02d318d3ec58f98b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0abc-9000000000-11e86d324c183174364e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-001i-0900000000-3ba18bb57823024db64e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03e9-9500000000-52f44695a6cfb6459105	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-03di-9800000000-264ee54a99e01e0d4e30	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9000000000-08f87dc3e44979542ca2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-06r6-9000000000-635fa893be82ffdeca97	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-03e9-9600000000-09232c8766303805f765	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0900000000-4c88765919efa0ec2d2d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03ea-6900000000-301590fbe90692448d5e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052g-9100000000-d6a51790ce1df14a067a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002r-9400000000-e43a7a5cb44f6c461544	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-053r-9800000000-56b95ef43b164db5524d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-1434c5ce1e9649c1cbf1	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum