Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-26 07:17:48 UTC |
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Update Date | 2016-11-09 01:21:27 UTC |
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Accession Number | CHEM036184 |
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Identification |
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Common Name | Sialyl Lea tetra |
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Class | Small Molecule |
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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, 2318868; 10683228, 1778981). |
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Contaminant Sources | |
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Contaminant Type | Not Available |
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Chemical Structure | |
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Synonyms | Value | Source |
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NeuAca2->3galb1->3(fuca1->4)glcnac | HMDB | 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 | HMDB | 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 | HMDB | (2S,4S,5R)-2-{[(2R,3R,5S,6R)-3,5-dihydroxy-2-{[(2S,3R,5S,6R)-3-[(1-hydroxyethylidene)amino]-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}-6-(hydroxymethyl)oxan-4-yl]oxy}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate | Generator, HMDB |
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Chemical Formula | C37H62N2O28 |
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Average Molecular Mass | 982.885 g/mol |
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Monoisotopic Mass | 982.349 g/mol |
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CAS Registry Number | 127321-43-1 |
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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 |
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Traditional 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 |
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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 |
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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 |
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InChI Key | ARDCDNROJUBBMX-NJMSAGAYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as n-acylneuraminic acids. These are neuraminic acids carrying an N-acyl substituent. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | N-acylneuraminic acids |
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Alternative Parents | |
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Substituents | - Oligosaccharide
- N-acylneuraminic acid
- Neuraminic acid
- N-acyl-alpha-hexosamine
- Fatty acyl glycoside
- C-glucuronide
- Alkyl glycoside
- O-glycosyl compound
- Glycosyl compound
- C-glycosyl compound
- Ketal
- Fatty acyl
- Pyran
- Oxane
- Acetamide
- Alpha-hydroxyaldehyde
- Secondary carboxylic acid amide
- Secondary alcohol
- Carboxamide group
- Acetal
- Carboxylic acid derivative
- Carboxylic acid
- Oxacycle
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Polyol
- Alcohol
- Hydrocarbon derivative
- Carbonyl group
- Aldehyde
- Organic nitrogen compound
- Organopnictogen compound
- Primary alcohol
- Organic oxide
- Organonitrogen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Not Available |
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Cellular Locations | Not Available |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | Not Available |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Not Available |
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Appearance | Not Available |
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Experimental Properties | Property | Value |
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Melting Point | Not Available | Boiling Point | Not Available | Solubility | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0101042049-2386bb26b689ceadebaa | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-007o-1201097010-960be680245544466d14 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-02ai-5219183221-b0b3785bbeeefa884af5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0h9c-4630000019-7e005233b30d61a5cdf5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0bti-9545012114-bb18cfe2fe1ad82b2ede | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0bt9-8493010000-de6fa864d5415700c8f0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0f89-0020000039-b3831e6afeae7fb00351 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03kd-5910000178-e6e6a1bc735668d3e845 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-8005132901-e96a09529f33e5718bf4 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014i-0000000089-b59c5393dada41f7b940 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01di-0200006398-c5bc8afeb480d82478c8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ac1-9600005022-054ba59bc8acdaf22a70 | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | Not Available |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | Not Available |
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Uses/Sources | Not Available |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Not Available |
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Concentrations |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB0006633 |
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FooDB ID | FDB024016 |
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Phenol Explorer ID | Not Available |
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KNApSAcK ID | Not Available |
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BiGG ID | Not Available |
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BioCyc ID | Not Available |
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METLIN ID | Not Available |
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PDB ID | Not Available |
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Wikipedia Link | Not Available |
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Chemspider ID | 35016015 |
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ChEBI ID | Not Available |
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PubChem Compound ID | 53477879 |
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Kegg Compound ID | Not Available |
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YMDB ID | Not Available |
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ECMDB ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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MSDS | Not Available |
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General References | 1. 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 | 2. 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. | 3. 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. |
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