Showing metabocard for Sialyl-Lewis X (BMDB0006565)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:23:26 UTC
Update Date2020-04-22 15:17:53 UTC
BMDB IDBMDB0006565
Secondary Accession Numbers
  • BMDB06565
Metabolite Identification
Common NameSialyl-Lewis X
DescriptionSialyl-Lewis X belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Based on a literature review very few articles have been published on Sialyl-Lewis X.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
SLexChEMBL, HMDB
Sialyl lewisxChEMBL, HMDB
Sialyl lewis-XChEMBL, HMDB
Sialyl lexChEMBL, HMDB
3'-Sialyl-lewis XHMDB
3'-Sialyl-lewis-X tetrasaccharideHMDB
3'-SLeXHMDB
a-NeuNAc-(2>3)-b-D-gal-(1>4)(a-L-fuc-[1>3])-D-glcnacHMDB
alpha-NeuNAc-(2>3)-beta-delta-gal-(1>4)(a-L-fuc-[1>3])-delta-glcnacHMDB
Sialyl lex triHMDB
SSEA 1HMDB, MeSH
3 alpha Fucosyl N acetyl lactosamineMeSH, HMDB
3 alpha-Fucosyl-N-acetyl lactosamineMeSH, HMDB
Antigen, lewis XMeSH, HMDB
Antigens, CD15MeSH, HMDB
CD15 AntigenMeSH, HMDB
CD15 AntigensMeSH, HMDB
Embryonic antigen-1, stage-specificMeSH, HMDB
Galbeta(1-4)fucalpha(1-3)glcnacMeSH, HMDB
Hapten XMeSH, HMDB
Le(X) antigenMeSH, HMDB
Leu m1 antigensMeSH, HMDB
Leu-m1 antigensMeSH, HMDB
Lewis X antigenMeSH, HMDB
Lewis X haptenMeSH, HMDB
SSEA 1 determinantMeSH, HMDB
SSEA-1MeSH, HMDB
SSEA-1 determinantMeSH, HMDB
Stage specific embryonic antigen 1MeSH, HMDB
Stage-specific embryonic antigen-1MeSH, HMDB
X Antigen, lewisMeSH, HMDB
X Hapten, lewisMeSH, HMDB
(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3R,4R,5R)-1,2-dihydroxy-5-[(1-hydroxyethylidene)amino]-6-oxo-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateGenerator, HMDB
Chemical FormulaC31H52N2O23
Average Molecular Weight820.7442
Monoisotopic Molecular Weight820.29608598
IUPAC Name(2S,4S,5R,6R)-5-acetamido-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3R,4R,5R)-5-acetamido-1,2-dihydroxy-6-oxo-4-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}hexan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Namesialyl-lewis X
CAS Registry Number98603-84-0
SMILES
[H][C@]1(O[C@@](C[C@H](O)[C@H]1NC(C)=O)(O[C@H]1[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]([C@H](O)CO)[C@H](O[C@@H]2O[C@@H](C)[C@@H](O)[C@@H](O)[C@@H]2O)[C@@H](NC(C)=O)C=O)[C@@H]1O)C(O)=O)[C@H](O)[C@H](O)CO
InChI Identifier
InChI=1S/C31H52N2O23/c1-9-18(43)21(46)22(47)28(51-9)53-24(12(5-34)32-10(2)38)25(15(42)7-36)54-29-23(48)27(20(45)16(8-37)52-29)56-31(30(49)50)4-13(40)17(33-11(3)39)26(55-31)19(44)14(41)6-35/h5,9,12-29,35-37,40-48H,4,6-8H2,1-3H3,(H,32,38)(H,33,39)(H,49,50)/t9-,12-,13-,14+,15+,16+,17+,18+,19+,20-,21+,22-,23+,24+,25+,26+,27-,28-,29-,31-/m0/s1
InChI KeyLAQPKDLYOBZWBT-NYLDSJSYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGlutamine and derivatives
Alternative Parents
Substituents
  • Glutamine or derivatives
  • Glutamic acid or derivatives
  • Hippuric acid or derivatives
  • Pterin
  • Alpha-amino acid
  • Aminobenzamide
  • Aminobenzoic acid or derivatives
  • Pteridine
  • L-alpha-amino acid
  • Benzoic acid or derivatives
  • Benzoyl
  • Phenylalkylamine
  • Aniline or substituted anilines
  • Gamma-keto acid
  • Aminopyrimidine
  • Aralkylamine
  • Beta-keto acid
  • Amino fatty acid
  • Pyrimidone
  • Secondary aliphatic/aromatic amine
  • Gamma-aminoketone
  • Pyrimidine
  • Pyrazine
  • Benzenoid
  • Fatty acyl
  • Monocyclic benzene moiety
  • Keto acid
  • N-acyl-amine
  • Carboxylic acid imide, n-substituted
  • Heteroaromatic compound
  • Carboxylic acid anhydride
  • Carboxylic acid imide
  • Dicarboximide
  • Vinylogous amide
  • Ketone
  • Amino acid
  • Secondary amine
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Primary amine
  • Organooxygen compound
  • Organic oxide
  • Primary aliphatic amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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-8.8ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)2.84ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count23ChemAxon
Hydrogen Donor Count15ChemAxon
Polar Surface Area410.71 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity172 m³·mol⁻¹ChemAxon
Polarizability77.51 ųChemAxon
Number of Rings3ChemAxon
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 (TMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_11) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_12) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_13) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_14) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_15) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_16) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zfr-0039047780-bd9a483433a6b32b3f21View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-1219050000-55b605a166d86dbfb321View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0hu0-2196012000-f5b9e98bca31bd11ab30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0kml-3812003940-5ce8467310926be298caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pdr-9657230210-501b68e6e411f1adc5e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-8459000000-c06d6848a870f6c1ededView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0le9-7140001890-9a9898e9a80d6b2a0f5dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-053r-3470032930-399f53553692504e461fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3092000000-571b2edb7a0141c71ab6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0003201290-ff78595d0f6dd1cd8d54View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0kn9-0394158260-4888247c7630f5b9b88aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01pa-3920000100-e100073c507f9d9a271eView in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0006565
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023975
KNApSAcK IDNot Available
Chemspider ID559072
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSialyl-Lewis X
METLIN IDNot Available
PubChem Compound643990
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNashed, Mina A.; Musser, John H. A facile and regioselective synthesis of partially benzoylated 3',4'-O-isopropylidene-b-lactosides as standardized key intermediates for sialyl Lewis X (sLeX) analogs. Carbohydrate Research (1993), 250(2), C1-C4.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. P-selectin
General function:
Not Available
Specific function:
Ca(2+)-dependent receptor for myeloid cells that binds to carbohydrates on neutrophils and monocytes (PubMed:7683458). Mediates the interaction of activated endothelial cells or platelets with leukocytes. The ligand recognized is sialyl-Lewis X. Mediates rapid rolling of leukocyte rolling over vascular surfaces during the initial steps in inflammation through interaction with SELPLG (By similarity).
Gene Name:
SELP
Uniprot ID:
P42201
Molecular weight:
71229.0