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
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