Sialyl Lex penta (CHEM036174)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 07:17:07 UTC
Update Date2016-11-09 01:21:27 UTC
Accession NumberCHEM036174
Identification
Common NameSialyl Lex penta
ClassSmall Molecule
DescriptionIn human leukocytes, sialyl Lex determinants bind selectins expressed on the blood vessel, endothelial cells and platelets, causing various cellular interactions and inducing inflammation. The sialyl Lex determinants of CD11/CD18 are shown to bind to E-selection in vitro, suggesting their involvement in the selectin-mediated adhesion process. ("Biology of the Sialic Acids" by Abraham Rosenberg).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-galactopyranosyl-(1->4)-O-[6-deoxy-alpha-L-galactopyranosyl-(1->3)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)- D-glucoseHMDB
O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-delta-galactopyranosyl-(1->4)-O-[6-deoxy-alpha-L-galactopyranosyl-(1->3)]-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-O-beta-delta-galactopyranosyl-(1->4)- D-glucoseHMDB
(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-5-[(1-hydroxyethylidene)amino]-2-(hydroxymethyl)-4-{[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylateGenerator, HMDB
Chemical FormulaC43H72N2O33
Average Molecular Mass1145.025 g/mol
Monoisotopic Mass1144.402 g/mol
CAS Registry Number127923-85-7
IUPAC Name(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-2-(hydroxymethyl)-4-{[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional Name(2S,4S,5R,6R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3S,4R,5R,6S)-6-{[(2R,3S,4S,5R,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-{[(2R,3R,4R,5R)-1,2,4,5-tetrahydroxy-6-oxohexan-3-yl]oxy}oxan-4-yl]oxy}-5-acetamido-2-(hydroxymethyl)-4-{[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-5-acetamido-4-hydroxy-6-[(2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
SMILESC[C@@H]1OC(O[C@@H]2[C@@H](NC(C)=O)[C@H](O[C@H]3[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)[C@@H]3O)O[C@H](CO)[C@H]2O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)[C@@H](O3)C(O)[C@H](O)CO)C(O)=O)[C@H]2O)[C@@H](O)[C@H](O)[C@@H]1O
InChI IdentifierInChI=1S/C43H72N2O33/c1-11-23(58)28(63)29(64)39(69-11)75-35-22(45-13(3)53)38(76-36-26(61)18(8-49)70-40(30(36)65)73-32(17(57)7-48)24(59)15(55)5-46)72-20(10-51)33(35)74-41-31(66)37(27(62)19(9-50)71-41)78-43(42(67)68)4-14(54)21(44-12(2)52)34(77-43)25(60)16(56)6-47/h5,11,14-41,47-51,54-66H,4,6-10H2,1-3H3,(H,44,52)(H,45,53)(H,67,68)/t11-,14-,15-,16+,17+,18+,19+,20+,21+,22+,23+,24+,25?,26-,27-,28+,29-,30+,31+,32+,33+,34+,35+,36-,37-,38-,39?,40-,41-,43-/m0/s1
InChI KeyMIEFTLKRJLOCFD-WXGLPKFQSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentN-acylneuraminic acids
Alternative Parents
Substituents
  • Oligosaccharide
  • N-acylneuraminic acid
  • Neuraminic acid
  • Fatty acyl glycoside
  • N-acyl-alpha-hexosamine
  • C-glucuronide
  • Alkyl glycoside
  • C-glycosyl compound
  • Glycosyl compound
  • O-glycosyl compound
  • Ketal
  • Beta-hydroxy aldehyde
  • Fatty acyl
  • Pyran
  • Oxane
  • Acetamide
  • Alpha-hydroxyaldehyde
  • Carboxamide group
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Polyol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Oxacycle
  • Acetal
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Primary alcohol
  • Aldehyde
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility130 g/LALOGPS
logP-2.5ALOGPS
logP-12ChemAxon
logS-0.95ALOGPS
pKa (Strongest Acidic)2.84ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count33ChemAxon
Hydrogen Donor Count21ChemAxon
Polar Surface Area569.01 ŲChemAxon
Rotatable Bond Count24ChemAxon
Refractivity236.83 m³·mol⁻¹ChemAxon
Polarizability109 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-003r-1900002023-05046d9782204ccbd25cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-053l-2702014491-926bd20eeca9a075557eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ec-6900043232-66b10eb05331ef2559baSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00c9-6901000000-ba5093251116d585efc8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0570-8914001020-4790d75ea5a47b1e61c1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a6r-8946400000-f70a53c6ea23b405c910Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-7940000002-28c467b4f36f1edb0b04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-05dl-9310000002-bc81e02856871828cd00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100010000-4fb87c5917a9e0994421Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-032a-2900000016-3f2ffb2049babb559317Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-8900030045-a77d6a05f074f93fc9b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006t-9510400001-6f2c36ec76654d25e217Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0006614
FooDB IDFDB024005
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID59651616
ChEBI IDNot Available
PubChem Compound ID131750431
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available