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Showing Compound Glucosamine (FDB022668)

Record Information
Version1.0
Creation date2011-09-21 00:17:41 UTC
Update date2019-11-26 03:21:05 UTC
Primary IDFDB022668
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlucosamine
DescriptionGlucosamine 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 is a very strong basic compound (based on its pKa). Glucosamine has been detected, but not quantified in, several different foods, such as milk (cow), carrots, green bell peppers, common beans, and yellow bell peppers. This could make glucosamine a potential biomarker for the consumption of these foods.
CAS Number3416-24-8
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
2 amino 2 DeoxyglucoseMeSH
2-amino-2-DeoxyglucoseMeSH
Glucosamine sulfateMeSH
Sulfate, glucosamineMeSH
Dona SMeSH
Opfermann brand OF glucosamine sulfateMeSH
HespercorbinMeSH
DonaMeSH
Fides ecopharma brand OF glucosamine sulfateMeSH
Rottapharm brand OF glucosamine sulfateMeSH
XicilMeSH
(+)-2-amino-2-Deoxy-D-glucopyranoseHMDB
(3R,4R,5S,6R)-3-amino-6-(Hydroxymethyl)oxane-2,4,5-triolHMDB
2-Amino-2-deoxy-D-glucopyranosemanual
2-Amino-2-deoxy-D-glucosemanual
2-Amino-2-deoxyglucosehmdb
2-Aminoglucosehmdb
2-Deoxy-2-amino-D-glucosehmdb
2-Deoxy-2-aminoglucosehmdb
Chitosaminedb_source
Cosaminhmdb
D-(+)-Glucosaminehmdb
D-Glucosaminemanual
Glucosamine, 9CI,8CIdb_source
Predicted Properties
PropertyValueSource
Water Solubility551 g/LALOGPS
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
Polarizability16.58 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H13NO5
IUPAC name(3S,4S,5R,6S)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
InChI IdentifierInChI=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?/m0/s1
InChI KeyMSWZFWKMSRAUBD-HOWGCPQDSA-N
Isomeric SMILES[H][C@@]1(N)C(O)O[C@@]([H])(CO)[C@]([H])(O)[C@@]1([H])O
Average Molecular Weight179.1711
Monoisotopic Molecular Weight179.079372531
Classification
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 DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-4900000000-364d52fc6e7e423f52bb2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-00di-9000000000-762e016c89a40a9e3f492012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00di-9000000000-bd04d561d78f2abad2292012-07-24View Spectrum
NMR
TypeDescriptionView
2D NMR[1H, 1H]-TOCSY 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID388352
ChEMBL IDCHEMBL493287
KEGG Compound IDC00329
Pubchem Compound ID439213
Pubchem Substance IDNot Available
ChEBI ID47977
Phenol-Explorer IDNot Available
DrugBank IDDB01296
HMDB IDHMDB01514
CRC / DFC (Dictionary of Food Compounds) IDGZV30-O:GZV56-A
EAFUS IDNot Available
Dr. Duke IDD-GLUCOSAMINE|GLUCOSAMINE
BIGG ID34633
KNApSAcK IDNot Available
HET ID1QGI
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGlucosamine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Anti-arthritic52217 An agent that reduces joint inflammation and alleviates symptoms of arthritis, commonly used in managing rheumatoid arthritis, osteoarthritis, and other inflammatory joint disorders, to improve mobility and quality of life.DUKE
Anti-flu22587 An agent that prevents or treats influenza virus infections, reducing symptoms and complications. Its biological role involves blocking viral replication, and its therapeutic applications include prophylaxis and treatment of flu outbreaks. Key medical uses include reducing the risk of flu-related hospitalizations and mortality, especially in high-risk populations such as the elderly and young children.DUKE
Anti-herpetic22587 An agent that inhibits the replication of herpes viruses, reducing symptoms and severity of infections. Therapeutically, it is used to treat herpes simplex (HSV-1 and HSV-2) and varicella-zoster virus (VZV) infections, commonly used in managing genital herpes, cold sores, and shingles.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
Enzymes
NameGene NameUniProt ID
GlucokinaseGCKP35557
Hexokinase-3HK3P52790
Hexokinase-2HK2P52789
Hexokinase-1HK1P19367
Tumor necrosis factorTNFP01375
Di-N-acetylchitobiaseCTBSQ01459
Peptide-N(4)-(N-acetyl-beta-glucosaminyl)asparagine amidaseNGLY1Q96IV0
Pathways
NameSMPDB LinkKEGG Link
Amino Sugar MetabolismSMP00045 map00520
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).