Showing metabocard for Lewis a trisaccharide (BMDB0006582)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:23:41 UTC
Update Date2020-04-22 15:17:57 UTC
BMDB IDBMDB0006582
Secondary Accession Numbers
  • BMDB06582
Metabolite Identification
Common NameLewis a trisaccharide
DescriptionLewis a trisaccharide belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol. Based on a literature review a significant number of articles have been published on Lewis a trisaccharide.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-O-b-D-Galactopyranosyl-4-O-a-L-fucopyranosyl-N-acetyl-D-glucosamineHMDB
3-O-beta-D-Galactopyranosyl-4-O-alpha-L-fucopyranosyl-N-acetyl-D-glucosamineHMDB
LeaHMDB
Lea triHMDB
Lea trisaccharideHMDB
Lewis aHMDB
N-Acetyl-4-O-a-L-fucosyl-3-O-b-D-galactosyl-glucosamineHMDB
N-Acetyl-4-O-alpha-L-fucosyl-3-O-beta-D-galactosyl-glucosamineHMDB
N-Acetyl-4-O-alpha-L-fucosyl-3-O-beta-delta-galactosyl-glucosamineHMDB
O-6-Deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-D-galactopyranosyl-(1->3)]-2-(acetylamino)-2-deoxy-D-glucoseHMDB
O-6-Deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-delta-galactopyranosyl-(1->3)]-2-(acetylamino)-2-deoxy-delta-glucoseHMDB
O-a-L-Fucopyranosyl-(1->4)-O-[b-D-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-D-glucoseHMDB
O-alpha-L-Fucopyranosyl-(1->4)-O-[b-D-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-D-glucoseHMDB
O-alpha-L-Fucopyranosyl-(1->4)-O-[beta-D-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-D-glucoseHMDB
O-alpha-L-Fucopyranosyl-(1->4)-O-[beta-delta-galactopyranosyl-(1->3)]-2-acetamido-2-deoxy-delta-glucoseHMDB
N-[(2R,3R,4R,5R)-5,6-Dihydroxy-1-oxo-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]ethanimidateGenerator, HMDB
Chemical FormulaC20H35NO15
Average Molecular Weight529.4896
Monoisotopic Molecular Weight529.200669455
IUPAC NameN-[(2R,3R,4R,5R)-5,6-dihydroxy-1-oxo-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]acetamide
Traditional NameN-[(2R,3R,4R,5R)-5,6-dihydroxy-1-oxo-3-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-2-yl]acetamide
CAS Registry Number56570-03-7
SMILES
[H][C@@](O[C@@H]1O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]1O)([C@H](O)CO)[C@]([H])(O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O)[C@@H](NC(C)=O)C=O
InChI Identifier
InChI=1S/C20H35NO15/c1-6-11(27)13(29)15(31)19(33-6)36-18(9(26)4-23)17(8(3-22)21-7(2)25)35-20-16(32)14(30)12(28)10(5-24)34-20/h3,6,8-20,23-24,26-32H,4-5H2,1-2H3,(H,21,25)/t6-,8-,9+,10+,11+,12-,13+,14-,15-,16+,17+,18+,19-,20-/m0/s1
InChI KeyHHQLEBOUBWWITP-MBKDEEHCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl glycosides
Direct ParentFatty acyl glycosides of mono- and disaccharides
Alternative Parents
Substituents
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Glycosyl compound
  • O-glycosyl compound
  • Amino saccharide
  • Monosaccharide
  • Oxane
  • Acetamide
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Carboxamide group
  • Acetal
  • Organoheterocyclic compound
  • Polyol
  • Oxacycle
  • Carboxylic acid derivative
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Carbonyl group
  • Organic nitrogen compound
  • Aldehyde
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Cytoplasm
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-2.3ALOGPS
logP-6.4ChemAxon
logS-0.64ALOGPS
pKa (Strongest Acidic)11.31ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area265.16 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity111.73 m³·mol⁻¹ChemAxon
Polarizability49.38 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Biological Properties
Cellular Locations
  • Cell membrane
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006582
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023984
KNApSAcK IDNot Available
Chemspider ID30776578
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477858
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceMakimura, Yutaka; Ishida, Hideharu; Kiso, Makoto; Hasegawa, Akira. Synthetic studies of sialoglycoconjugates. 93. Synthetic studies on tumor-associated antigens: efficient syntheses of Lea and sialyl-Lea oligosaccharides, and their deaminated analogs. ChemInform 28(35) · August 2010
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available