Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-24 10:05:09 UTC
Update Date2021-09-14 15:18:16 UTC
HMDB IDHMDB0006565
Secondary Accession Numbers
  • HMDB06565
Metabolite Identification
Common NameSialyl-Lewis X
DescriptionCarbohydrate antigen which is accumulated in various human cancer tissues and secreted into the blood stream. The carbohydrate moiety can be further modified with fucose or sialic acid. Monoclonal antibodies have been determined which can discriminate each subgroup of this antigen in the sera of cancer patients. Sialyl SSEA-1 antigen is particularly elevated in the sera of patients with a variety of tumors.
Structure
Data?1582752392
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
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility45.5 g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+255.26830932474
DeepCCS[M-H]-253.54530932474
DeepCCS[M-2H]-287.57630932474
DeepCCS[M+Na]+261.53330932474
AllCCS[M+H]+263.132859911
AllCCS[M+H-H2O]+263.232859911
AllCCS[M+NH4]+262.932859911
AllCCS[M+Na]+262.932859911
AllCCS[M-H]-274.232859911
AllCCS[M+Na-2H]-277.632859911
AllCCS[M+HCOO]-281.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Sialyl-Lewis X[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)CO4731.8Standard polar33892256
Sialyl-Lewis X[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)CO5240.0Standard non polar33892256
Sialyl-Lewis X[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)CO6066.2Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Sialyl-Lewis X GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sialyl-Lewis X GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sialyl-Lewis X GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sialyl-Lewis X GC-MS (TMS_1_4) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sialyl-Lewis X GC-MS (TMS_1_5) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sialyl-Lewis X GC-MS (TMS_1_6) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sialyl-Lewis X GC-MS (TMS_1_7) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sialyl-Lewis X GC-MS (TMS_1_8) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sialyl-Lewis X GC-MS (TMS_1_9) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sialyl-Lewis X GC-MS (TMS_1_10) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sialyl-Lewis X GC-MS (TMS_1_11) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sialyl-Lewis X GC-MS (TMS_1_12) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sialyl-Lewis X GC-MS (TMS_1_13) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sialyl-Lewis X GC-MS (TMS_1_14) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sialyl-Lewis X GC-MS (TMS_1_15) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Sialyl-Lewis X GC-MS (TMS_1_16) - 70eV, PositiveNot Available2021-10-19Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyl-Lewis X 10V, Positive-QTOFsplash10-0zfr-0039047780-bd9a483433a6b32b3f212017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyl-Lewis X 20V, Positive-QTOFsplash10-001i-1219050000-55b605a166d86dbfb3212017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyl-Lewis X 40V, Positive-QTOFsplash10-0hu0-2196012000-f5b9e98bca31bd11ab302017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyl-Lewis X 10V, Negative-QTOFsplash10-0kml-3812003940-5ce8467310926be298ca2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyl-Lewis X 20V, Negative-QTOFsplash10-0pdr-9657230210-501b68e6e411f1adc5e32017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyl-Lewis X 40V, Negative-QTOFsplash10-0a4i-8459000000-c06d6848a870f6c1eded2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyl-Lewis X 10V, Negative-QTOFsplash10-0le9-7140001890-9a9898e9a80d6b2a0f5d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyl-Lewis X 20V, Negative-QTOFsplash10-053r-3470032930-399f53553692504e461f2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyl-Lewis X 40V, Negative-QTOFsplash10-014i-3092000000-571b2edb7a0141c71ab62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyl-Lewis X 10V, Positive-QTOFsplash10-0fk9-0003201290-ff78595d0f6dd1cd8d542021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyl-Lewis X 20V, Positive-QTOFsplash10-0kn9-0394158260-4888247c7630f5b9b88a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Sialyl-Lewis X 40V, Positive-QTOFsplash10-01pa-3920000100-e100073c507f9d9a271e2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents 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)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in sialyltransferase activity
Specific function:
Involved in the synthesis of sialyl-paragloboside, a precursor of sialyl-Lewis X determinant. Has a alpha-2,3- sialyltransferase activity toward Gal-beta1,4-GlcNAc structure on glycoproteins and glycolipids. Has a restricted substrate specificity, it utilizes Gal-beta1,4-GlcNAc on glycoproteins, and neolactotetraosylceramide and neolactohexaosylceramide, but not lactotetraosylceramide, lactosylceramide or asialo-GM1
Gene Name:
ST3GAL6
Uniprot ID:
Q9Y274
Molecular weight:
38213.3
General function:
Involved in binding
Specific function:
Ca(2+)-dependent receptor for myeloid cells that binds to carbohydrates on neutrophils and monocytes. 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 PSGL1
Gene Name:
SELP
Uniprot ID:
P16109
Molecular weight:
90833.1