Showing Compound Card for Galactosamine (CDB000369)

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Record Information
Version1.0
Created at2020-03-19 00:33:21 UTC
Updated at2020-11-18 16:35:06 UTC
CannabisDB IDCDB000369
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameGalactosamine
DescriptionGalactosamine or D-galactosamine, also known as D-chondrosamine or 2-amino-2-deoxy-D-galactose, is a hexosamine derived from galactose. It is a member of the class of compounds known as hexoses. Hexoses are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. D-galactosamine is soluble in water and a relatively strong base (based on its pKa). Galactosamine is a ubiquitous compound found in bacteria, plants and animals. Galactosamine is one of several aminosugars found in cannabis plants (PMID: 6991645 ). Evidently Cannabis sativa is one of only a handful of higher plants that synthesizes galactosamine. In humans, galactosamine is an asparagine-linked constituent of some glycoprotein hormones such as follicle-stimulating hormone (FSH) and luteinizing hormone (LH). An important derivative of galactosamine is N-acetyl-galactosamine, which is a major component of chondroitin and chondroitin sulfate (cartilage). Galactosamine is also used in the synthesis of bacterial cell walls (especially in the synthesis of the lipopolysaccharide or O-antigen) in streptococci bacteria (PMID: 4629249 ). Galactosamine is a hepatotoxin and is sometimes used either alone or in combination with lipopolysaccharide (LPS) in rodent models to induce liver failure (PMID: 12625810 ). Galactosamine induces depletion of UTP, UDP and UMP selectively, which is essential for RNA and protein synthesis. RNA and protein synthesis is especially high in metabolically actives tissues such as the liver, which partly explains the toxicity of galactosamine to these tissues (PMID: 11051199 ). Galactosamine is metabolized via the Leloir pathway of galactose metabolism, which generates dead-end uridine derivatives of galactosamine. UDP-galactosamine (and by inference, galactosamine) is an inhibitor of UDP-galactose-4′ epimerase.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
D-ChondrosamineChEBI
D-GalactosamineChEBI
D-GalNChEBI
GalactosamineMeSH
Chemical FormulaC6H13NO5
Average Molecular Weight179.17
Monoisotopic Molecular Weight179.0794
IUPAC Name(2R,3R,4R,5R)-2-amino-3,4,5,6-tetrahydroxyhexanal
Traditional NameD-galactosamine
CAS Registry Number7535-00-4
SMILES
N[C@@H](C=O)[C@@H](O)[C@@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C6H13NO5/c7-3(1-8)5(11)6(12)4(10)2-9/h1,3-6,9-12H,2,7H2/t3-,4+,5+,6-/m0/s1
InChI KeyFZHXIRIBWMQPQF-KCDKBNATSA-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
  • Beta-hydroxy aldehyde
  • 1,3-aminoalcohol
  • Secondary alcohol
  • Polyol
  • Organic nitrogen compound
  • Primary amine
  • Primary alcohol
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Aldehyde
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Role

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point180 °CWikipedia
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.6ALOGPS
logP-3.7ChemAxon
logS0.04ALOGPS
pKa (Strongest Acidic)12.77ChemAxon
pKa (Strongest Basic)6.86ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area124.01 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity39 m³·mol⁻¹ChemAxon
Polarizability16.57 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSGalactosamine, 5 TMS, GC-MS Spectrumsplash10-0udi-0190000000-44a53c7fff16ea23ba8dSpectrum
GC-MSGalactosamine, 1 MEOX; 5 TMS, GC-MS Spectrumsplash10-0a4i-0942000000-2bfc11c528ce6d61d91cSpectrum
GC-MSGalactosamine, 1 MEOX; 5 TMS, GC-MS Spectrumsplash10-0a4i-0962000000-7144c78122b49c4d7363Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ 10V, positivesplash10-03di-0900000000-87974d07382269cc212a2020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 17V, positivesplash10-004i-2900000000-31c21d742ea1131adc532020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-001i-0900000000-7dccd909d21d233982842020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-001i-0900000000-d0dfc7f5a3255d5792e32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-01q9-0900000000-294b83881430616133c02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-03e9-0900000000-c1f5bb712d680c983a6f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-03di-1900000000-e8c8f87a4625833de9ef2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-03k9-6900000000-260303742e69f79b4bd02020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-00di-9300000000-33da16156362acdeb3492020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-00di-9100000000-47f7fd935b166f202e402020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-00di-9000000000-83a682582ce0244bd7122020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, positivesplash10-03di-0900000000-fd755fa4096a22adbc822020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, positivesplash10-0002-9000000000-1e7543074f76fe73c9d12020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, positivesplash10-004j-4900000000-84a64488fc68b095bb0d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 12V, positivesplash10-004m-4900000000-fd0c74759fe6c02f24702020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-03di-0900000000-e989858309a45dfa76942020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-03di-0900000000-4a61e4f18140fb2278a72020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-03di-2900000000-c7bfca612be3b662d7312020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-03k9-7900000000-03a636f65fbdc5b936342020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-00di-9300000000-43d509f97f04f33b87e62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-00di-9100000000-6519242b8ac188a188f82020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-00di-9000000000-73148cf329b61d7ac4772020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-00di-9000000000-d20d408c6d85bd4915092020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-00di-9000000000-3830aa7ba823b63092632020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-00di-9000000000-fc956aa4a8967ffb4d0f2020-07-22View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound2794221
PDB IDNot Available
ChEBI ID60313
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Mukasa H, Slade HD: Chemical composition and immunological specificity of the streptococcal group O cell wall polysaccharide antigen. Infect Immun. 1972 May;5(5):707-14. [PubMed:4629249 ]
  3. Ferencikova R, Cervinkova Z, Drahota Z: Hepatotoxic effect of D-galactosamine and protective role of lipid emulsion. Physiol Res. 2003;52(1):73-8. [PubMed:12625810 ]
  4. Kmiec Z, Smolenski RT, Zych M, Mysliwski A: The effects of galactosamine on UTP levels in the livers of young, adult and old rats. Acta Biochim Pol. 2000;47(2):349-53. [PubMed:11051199 ]