Showing metabocard for Glucosamine (BMDB0001514)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:47:03 UTC
Update Date2020-05-21 16:26:54 UTC
BMDB IDBMDB0001514
Secondary Accession Numbers
  • BMDB01514
Metabolite Identification
Common NameGlucosamine
DescriptionGlucosamine, also known as dona or chitosamine, 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. Glucosamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. Glucosamine exists in all living organisms, ranging from bacteria to humans. Glucosamine can be converted into glucosamine 6-phosphate; which is mediated by the enzyme hexokinase-1. In cattle, glucosamine is involved in the metabolic pathway called the amino sugar metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Amino-2-deoxy-D-glucoseChEBI
ChitosamineChEBI
D-GlucosamineChEBI
(+)-2-Amino-2-deoxy-D-glucopyranoseHMDB
(3R,4R,5S,6R)-3-Amino-6-(hydroxymethyl)oxane-2,4,5-triolHMDB
2-Amino-2-deoxy-D-glucopyranoseHMDB
2-Amino-2-deoxyglucoseHMDB
2-AminoglucoseHMDB
2-Deoxy-2-amino-D-glucoseHMDB
2-Deoxy-2-aminoglucoseHMDB
CosaminHMDB
D-(+)-GlucosamineHMDB
DonaHMDB
Fides ecopharma brand OF glucosamine sulfateHMDB
Rottapharm brand OF glucosamine sulfateHMDB
XicilHMDB
2 Amino 2 deoxyglucoseHMDB
Glucosamine sulfateHMDB
Sulfate, glucosamineHMDB
Dona SHMDB
Opfermann brand OF glucosamine sulfateHMDB
HespercorbinHMDB
Chemical FormulaC6H13NO5
Average Molecular Weight179.1711
Monoisotopic Molecular Weight179.079372531
IUPAC Name(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
Traditional Nameglucosamine
CAS Registry Number3416-24-8
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 KeyMSWZFWKMSRAUBD-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
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 FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
StatusDetected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.7ALOGPS
logP-3ChemAxon
logS0.49ALOGPS
pKa (Strongest Acidic)11.73ChemAxon
pKa (Strongest Basic)8.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area116.17 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity37.58 m³·mol⁻¹ChemAxon
Polarizability16.87 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06tr-9300000000-7e2a89f48724cdda814cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-0ul9-9847700000-b4779809586433e7ec78View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-4900000000-364d52fc6e7e423f52bbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-762e016c89a40a9e3f49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-bd04d561d78f2abad229View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-9500000000-9bfc2897a4b66f71c7a1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0007-9000000000-f842b779439be8970cd9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-074i-9000000000-622ec0743231c0cbaca6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03e9-9700000000-5087af92679b2640ba6cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-b9ba212915cbdaed8628View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-2d1825b518f09745e036View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-03la-9100000000-3da7ee17d7512a59e3efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03e9-9400000000-cca17ef05a47a7be4d43View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-01x0-9500000000-5fbd02d318d3ec58f98bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0abc-9000000000-11e86d324c183174364eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 0V, Positivesplash10-001i-0900000000-3ba18bb57823024db64eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03e9-9500000000-52f44695a6cfb6459105View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-03di-9800000000-264ee54a99e01e0d4e30View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00dl-9000000000-08f87dc3e44979542ca2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-06r6-9000000000-635fa893be82ffdeca97View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-03e9-9600000000-09232c8766303805f765View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-4c88765919efa0ec2d2dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-6900000000-301590fbe90692448d5eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052g-9100000000-d6a51790ce1df14a067aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002r-9400000000-e43a7a5cb44f6c461544View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-9800000000-56b95ef43b164db5524dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-1434c5ce1e9649c1cbf1View in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
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)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Cartilage
  • Epidermis
  • Fibroblasts
  • Intestine
  • Liver
  • Milk
  • Platelet
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
CartilageExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
FibroblastsExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
IntestineExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal		 details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
PlateletExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001514
DrugBank IDDB01296
Phenol Explorer Compound IDNot Available
FooDB IDFDB022668
KNApSAcK IDNot Available
Chemspider ID388352
KEGG Compound IDC00329
BioCyc IDNot Available
BiGG ID34633
Wikipedia LinkGlucosamine
METLIN ID266
PubChem Compound439213
PDB IDNot Available
ChEBI ID47977
References
Synthesis ReferenceLi, Nan; Li, Jiheng. Preparation of D-glucosamine hydrochloride. Zhongguo Yaoke Daxue Xuebao (1997), 28(1), 56-58.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  2. Qian L, Zhao A, Zhang Y, Chen T, Zeisel SH, Jia W, Cai W: Metabolomic Approaches to Explore Chemical Diversity of Human Breast-Milk, Formula Milk and Bovine Milk. Int J Mol Sci. 2016 Dec 17;17(12). pii: ijms17122128. doi: 10.3390/ijms17122128. [PubMed:27999311 ]

Enzymes

Enzyme Details
1. Hexokinase-1
General function:
Involved in ATP binding
Specific function:
Catalyzes the phosphorylation of various hexoses, such as D-glucose, D-glucosamine, D-fructose, D-mannose and 2-deoxy-D-glucose, to hexose 6-phosphate (D-glucose 6-phosphate, D-glucosamine 6-phosphate, D-fructose 6-phosphate, D-mannose 6-phosphate and 2-deoxy-D-glucose 6-phosphate, respectively). Does not phosphorylate N-acetyl-D-glucosamine (By similarity). Mediates the initial step of glycolysis by catalyzing phosphorylation of D-glucose to D-glucose 6-phosphate (By similarity). Involved in innate immunity and inflammation by acting as a pattern recognition receptor for bacterial peptidoglycan. When released in the cytosol, N-acetyl-D-glucosamine component of bacterial peptidoglycan inhibits the hexokinase activity of HK1 and causes its dissociation from mitochondrial outer membrane, thereby activating the NLRP3 inflammasome (By similarity).
Gene Name:
HK1
Uniprot ID:
P27595
Molecular weight:
103064.0
Reactions
Glucosamine + Adenosine triphosphate → Glucosamine 6-phosphate + ADPdetails