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Human Metabolome Database Version 3.5

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Showing metabocard for Sialyl Lea tetra (HMDB06633)

Record Information
Version 3.5
Creation Date 2007-05-28 05:02:16 -0600
Update Date 2013-05-29 13:44:51 -0600
HMDB ID HMDB06633
Secondary Accession Numbers None
Metabolite Identification
Common Name Sialyl Lea tetra
Description Sialyl Lea tetra is a sialylated oligosaccharide normally occurring in human breast milk, with N-acetylglucosamine as the reducing-end residue. Sialylated oligosaccharides are important components of glycoproteins and glycolipids and also occur as free oligosaccharides in several body fluids. In human milk, both free and bound sialylated oligosaccharides have potential biological activity and are known to inhibit viral infection. Sialyl Lewis a is increasingly expressed in melanoma cells, and hypothetically immunotherapy eliciting a humoral response could be therapeutically effective against tumors. (PMID: 9426699 Link_out, 2318868 Link_out; 10683228, 1778981).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. NeuAca2->3Galb1->3(Fuca1->4)GlcNAc
  2. O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-galactopyranosyl-(1->3)-O-[6-deoxy-alpha-L-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)- D-Galactose
  3. O-(N-Acetyl-alpha-neuraminosyl)-(2->3)-O-beta-delta-galactopyranosyl-(1->3)-O-[6-deoxy-alpha-L-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)- D-Galactose
Chemical Formula C37H62N2O28
Average Molecular Weight 982.8848
Monoisotopic Molecular Weight 982.34890941
IUPAC Name (2S,4S,5R)-5-acetamido-2-{[(2R,3R,5S,6R)-2-{[(2S,3R,5S,6R)-3-acetamido-6-(hydroxymethyl)-2-{[(2R,3S,4S,5R)-2,4,5,6-tetrahydroxy-1-oxohexan-3-yl]oxy}-5-{[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-6-[(2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Traditional IUPAC Name (2S,4S,5R)-5-acetamido-2-{[(2R,3R,5S,6R)-2-{[(2S,3R,5S,6R)-3-acetamido-6-(hydroxymethyl)-2-{[(2R,3S,4S,5R)-2,4,5,6-tetrahydroxy-1-oxohexan-3-yl]oxy}-5-{[(3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-4-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxa
CAS Registry Number 127321-43-1
SMILES C[C@@H]1OC(O[C@@H]2[C@@H](CO)O[C@@H](O[C@H]([C@@H](O)C=O)[C@@H](O)[C@H](O)CO)[C@H](NC(C)=O)C2O[C@@H]2O[C@H](CO)[C@H](O)C(O[C@@]3(C[C@H](O)[C@@H](NC(C)=O)C(O3)C(O)[C@H](O)CO)C(O)=O)[C@H]2O)[C@@H](O)[C@H](O)[C@@H]1O
InChI Identifier InChI=1S/C37H62N2O28/c1-10-21(51)25(55)26(56)34(60-10)64-29-18(9-44)62-33(63-28(16(50)7-42)22(52)14(48)5-40)20(39-12(3)46)31(29)65-35-27(57)32(24(54)17(8-43)61-35)67-37(36(58)59)4-13(47)19(38-11(2)45)30(66-37)23(53)15(49)6-41/h7,10,13-35,40-41,43-44,47-57H,4-6,8-9H2,1-3H3,(H,38,45)(H,39,46)(H,58,59)/t10-,13-,14+,15+,16-,17+,18+,19+,20+,21+,22-,23?,24-,25+,26-,27+,28+,29+,30?,31?,32?,33-,34?,35-,37-/m0/s1
InChI Key ARDCDNROJUBBMX-NJMSAGAYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Oligosaccharides
Sub Class Hexose Oligosaccharides
Other Descriptors
  • Aliphatic Heteropolycyclic Compounds
Substituents
  • 1,2 Diol
  • 1,3 Aminoalcohol
  • Acetal
  • Aldehyde
  • Carboxamide Group
  • Carboxylic Acid
  • Fatty Acyl Glycoside
  • Glucosamine
  • Glyco Amino Acid
  • Glycosyl Compound
  • Mannosamine
  • N Acetylneuraminic Acid
  • Neuraminic Acid
  • O Glycosyl Compound
  • Oxane
  • Primary Alcohol
  • Pyranoid Amino Acid
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Sugar Acid
Direct Parent Hexose Oligosaccharides
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 79.2 g/L ALOGPS
LogP -2.62 ALOGPS
LogP -11 ChemAxon
LogS -1.09 ALOGPS
pKa (strongest acidic) 2.87 ChemAxon
pKa (strongest basic) -3.7 ChemAxon
Hydrogen Acceptor Count 28 ChemAxon
Hydrogen Donor Count 18 ChemAxon
Polar Surface Area 489.86 A2 ChemAxon
Rotatable Bond Count 21 ChemAxon
Refractivity 204.41 ChemAxon
Polarizability 92.66 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB024016
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB06633 Link_out
Metagene Link HMDB06633 Link_out
METLIN ID Not Available
PubChem Compound 53477879 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Roth, Steve. Enzymic preparation of oligosaccharides for conjugation to biological macromolecules. PCT Int. Appl. (1991), 50 pp. CODEN: PIXXD2 WO 9116449 A1 19911031 CAN 116:126977 AN 1992:126977
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Kitagawa H, Nakada H, Numata Y, Kurosaka A, Fukui S, Funakoshi I, Kawasaki T, Shimada I, Inagaki F, Yamashina I: Occurrence of tetra- and pentasaccharides with the sialyl-Le(a) structure in human milk. J Biol Chem. 1990 Mar 25;265(9):4859-62. Pubmed: 2318868 Link_out
  2. Ravindranath MH, Kelley MC, Jones RC, Amiri AA, Bauer PM, Morton DL: Ratio of IgG:IgM antibodies to sialyl Lewis(x) and GM3 correlates with tumor growth after immunization with melanoma-cell vaccine with different adjuvants in mice. Int J Cancer. 1998 Jan 5;75(1):117-24. Pubmed: 9426699 Link_out