Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-25 18:51:03 UTC |
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Update Date | 2016-11-09 01:17:34 UTC |
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Accession Number | CHEM022758 |
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Identification |
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Common Name | 3'-Sialyllactose |
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Class | Small Molecule |
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Description | Sialyllactose is an oligossaccharide found in both human breast milk and cow's milk. It is the predominant sialylated component in milk. Sialyllactose has recently been shown to inhibit the infection of HIV-1 virus. Sialyllactose is also responsible for the inhibitory activity of milk on cholera toxin. |
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Contaminant Sources | - FooDB Chemicals
- HMDB Contaminants - Urine
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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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(2>3')-a-sialyllactose | HMDB | (2>3')-alpha-sialyllactose | HMDB | 3'-(N-Acetyl-a-neuraminosyl)lactose | HMDB | 3'-(N-Acetyl-alpha-neuraminosyl)lactose | HMDB | 3'-a-Sialyllactose | HMDB | 3'-alpha-Sialyllactose | HMDB | 3'-Monosialyllactose | HMDB | 3'-N-Acetylneuraminyl-D-lactose | HMDB | 3'-N-Acetylneuraminyl-delta-lactose | HMDB | 3'-Sialyl-D-lactose | HMDB | 3'-Sialyl-delta-lactose | HMDB | 32-N-Acetyl-a-neuraminyllactose | HMDB | 32-N-Acetyl-alpha-neuraminyllactose | HMDB | a-Neu5ac-(2>3)-b-D-gal-(1>4)-D-GLC | HMDB | a2,3-Sialyllactose | HMDB | alpha-Neu5ac-(2>3)-beta-D-gal-(1>4)-D-GLC | HMDB | alpha-Neu5ac-(2>3)-beta-delta-gal-(1>4)-delta-GLC | HMDB | N-Acetylneuraminoyllactose | HMDB | N-Acetylneuraminyl-2-3-galactopyranosyl-1-4-glucopyranose | HMDB | (2S,4S,5R,6R)-2-{[(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}-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate | HMDB | 3'-Sialyllactose | MeSH |
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Chemical Formula | C23H39NO19 |
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Average Molecular Mass | 633.551 g/mol |
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Monoisotopic Mass | 633.212 g/mol |
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CAS Registry Number | 35890-38-1 |
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IUPAC Name | (2S,4S,5R,6R)-2-{[(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-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid |
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Traditional Name | (2S,4S,5R,6R)-2-{[(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-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid |
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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](O)C=O)[C@@H]1O)C(O)=O)[C@H](O)[C@H](O)CO |
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InChI Identifier | InChI=1S/C23H39NO19/c1-7(29)24-13-8(30)2-23(22(38)39,42-19(13)15(35)10(32)4-26)43-20-16(36)12(6-28)40-21(17(20)37)41-18(11(33)5-27)14(34)9(31)3-25/h3,8-21,26-28,30-37H,2,4-6H2,1H3,(H,24,29)(H,38,39)/t8-,9-,10+,11+,12+,13+,14+,15+,16-,17+,18+,19+,20-,21-,23-/m0/s1 |
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InChI Key | OIZGSVFYNBZVIK-FHHHURIISA-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
- Fatty acyl glycoside
- C-glucuronide
- Alkyl glycoside
- C-glycosyl compound
- O-glycosyl compound
- Glycosyl compound
- Ketal
- Beta-hydroxy aldehyde
- Fatty acyl
- Oxane
- Pyran
- Acetamide
- Alpha-hydroxyaldehyde
- Carboxamide group
- Secondary carboxylic acid amide
- Secondary alcohol
- Acetal
- Oxacycle
- Carboxylic acid derivative
- Carboxylic acid
- Organoheterocyclic compound
- Monocarboxylic acid or derivatives
- Polyol
- Alcohol
- Carbonyl group
- Hydrocarbon derivative
- Aldehyde
- Organic nitrogen compound
- Primary alcohol
- Organopnictogen compound
- 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 GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0329-9200136000-fffce6abd054ee490a92 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_11) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_12) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_13) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_14) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive | Not Available | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0006-0091000000-7e22772e5e2744079301 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-0229-0390000000-002eec5ec089f1eb0e5b | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-00xs-1930000000-89aed3dbc59d2c137408 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-02u1-1905068000-8188f1508e1a6fe4b08a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0059-1619000000-56b3f7f1b9406974b2ce | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03e9-8953000000-14875e5817ba52578c18 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0229-5910085000-1d9e7dc1c1b15e596033 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a73-9647001000-3efe2b78863a5580b526 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9843000000-ba45a1d17f709c61e7b9 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-001i-2120279000-b879570d20ee857cbdc0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-08gl-2010291000-4d99393826350dc02114 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9110000000-cc64071c39126f0d8560 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0frb-1400894000-dfbfe52cc93f55bebc01 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0irr-9414852000-d2182ab82f00048d4b3b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-024l-9614210000-0ef934abaed3d29bcc58 | 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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| Not Available |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | HMDB0000825 |
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FooDB ID | FDB021795 |
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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 | 5788 |
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PDB ID | Not Available |
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Wikipedia Link | Not Available |
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Chemspider ID | 110445 |
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ChEBI ID | Not Available |
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PubChem Compound ID | 123914 |
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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. Masuda, Mika; Kawase, Yuuji; Kawase, Mitsuo. Enzymic synthesis of (a2-3) sialyllactose using a membrane reactor. Seibutsu Kogaku Kaishi (2001), 79(9), 345-348. | 2. Renlund M, Chester MA, Lundblad A, Aula P, Raivio KO, Autio S, Koskela SL: Increased urinary excretion of free N-acetylneuraminic acid in thirteen patients with Salla disease. Eur J Biochem. 1979 Nov 1;101(1):245-50. | 3. Michalski JC, Corfield AP, Schauer R: Properties of human liver lysosomal sialidase. Biol Chem Hoppe Seyler. 1986 Aug;367(8):715-22. | 4. Watanabe Y, Shiratsuchi A, Shimizu K, Takizawa T, Nakanishi Y: Stimulation of phagocytosis of influenza virus-infected cells through surface desialylation of macrophages by viral neuraminidase. Microbiol Immunol. 2004;48(11):875-81. | 5. Parente F, Cucino C, Anderloni A, Grandinetti G, Bianchi Porro G: Treatment of Helicobacter pylori infection using a novel antiadhesion compound (3'sialyllactose sodium salt). A double blind, placebo-controlled clinical study. Helicobacter. 2003 Aug;8(4):252-6. | 6. Ha KT, Lee YC, Cho SH, Kim JK, Kim CH: Molecular characterization of membrane type and ganglioside-specific sialidase (Neu3) expressed in E. coli. Mol Cells. 2004 Apr 30;17(2):267-73. | 7. Ng KJ, Andresen BD, Hilty MD, Bianchine JR: Identification of long chain dicarboxylic acids in the serum of two patients with Reye's syndrome. J Chromatogr. 1983 Aug 12;276(1):1-10. | 8. Angeloni S, Ridet JL, Kusy N, Gao H, Crevoisier F, Guinchard S, Kochhar S, Sigrist H, Sprenger N: Glycoprofiling with micro-arrays of glycoconjugates and lectins. Glycobiology. 2005 Jan;15(1):31-41. Epub 2004 Sep 1. | 9. Burger O, Weiss E, Sharon N, Tabak M, Neeman I, Ofek I: Inhibition of Helicobacter pylori adhesion to human gastric mucus by a high-molecular-weight constituent of cranberry juice. Crit Rev Food Sci Nutr. 2002;42(3 Suppl):279-84. | 10. Hanasaki K, Powell LD, Varki A: Binding of human plasma sialoglycoproteins by the B cell-specific lectin CD22. Selective recognition of immunoglobulin M and haptoglobin. J Biol Chem. 1995 Mar 31;270(13):7543-50. | 11. Tringali C, Papini N, Fusi P, Croci G, Borsani G, Preti A, Tortora P, Tettamanti G, Venerando B, Monti E: Properties of recombinant human cytosolic sialidase HsNEU2. The enzyme hydrolyzes monomerically dispersed GM1 ganglioside molecules. J Biol Chem. 2004 Jan 30;279(5):3169-79. Epub 2003 Nov 12. | 12. Koseki M, Tsurumi K: A convenient method for the isolation of 3'-sialyllactose from normal human urine. J Biochem. 1977 Dec;82(6):1785-8. | 13. Serafini-Cessi F, Malagolini N, Dall'Olio F: Characterization and partial purification of beta-N-acetylgalactosaminyltransferase from urine of Sd(a+) individuals. Arch Biochem Biophys. 1988 Nov 1;266(2):573-82. | 14. Ding K, Ekberg T, Zeuthen J, Teneberg S, Karlsson KA, Rosen A: Monoclonal antibody against a lactose epitope of glycosphingolipids binds to melanoma tumour cells. Glycoconj J. 1993 Oct;10(5):395-405. |
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