Record Information |
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Version | 1.0 |
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Creation Date | 2016-05-26 07:17:09 UTC |
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Update Date | 2016-11-09 01:21:27 UTC |
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Accession Number | CHEM036175 |
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Identification |
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Common Name | Difucosyl-para-N-hexaose |
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Class | Small Molecule |
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Description | |
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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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Difucosyl-P-lacto-N-hexaose | HMDB | O-6-Deoxy-alpha-L-galactopyranosyl-(1->3)-O-[O-6-deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-D-galactopyranosyl-(1->3)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-beta-D-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->3)-O-beta-D-galactopyranosyl-(1->4)- D-glucose | HMDB | O-6-Deoxy-alpha-L-galactopyranosyl-(1->3)-O-[O-6-deoxy-alpha-L-galactopyranosyl-(1->4)-O-[beta-delta-galactopyranosyl-(1->3)]-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-beta-delta-galactopyranosyl-(1->4)]-O-2-(acetylamino)-2-deoxy-beta-delta-glucopyranosyl-(1->3)-O-beta-delta-galactopyranosyl-(1->4)- D-glucose | HMDB | N-[(2S,3R,4R,5S,6R)-2-{[(2S,3R,5S,6R)-2-{[(2R,3S,5R,6S)-6-{[(2R,3S,4S,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-{[(2S,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}-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]ethanimidate | Generator, HMDB |
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Chemical Formula | C52H88N2O39 |
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Average Molecular Mass | 1365.245 g/mol |
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Monoisotopic Mass | 1364.496 g/mol |
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CAS Registry Number | 64309-01-9 |
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IUPAC Name | N-[(2S,3R,4R,5S,6R)-2-{[(2S,3R,5S,6R)-2-{[(2R,3S,5R,6S)-6-{[(2R,3S,4S,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-{[(2S,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}-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide |
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Traditional Name | N-[(2S,3R,4R,5S,6R)-2-{[(2S,3R,5S,6R)-2-{[(2R,3S,5R,6S)-6-{[(2R,3S,4S,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-{[(2S,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}-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-{[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl]acetamide |
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SMILES | C[C@@H]1O[C@@H](O[C@@H]2[C@@H](CO)O[C@@H](OC3[C@@H](O)[C@@H](CO)O[C@@H](O[C@@H]4[C@@H](CO)O[C@@H](O[C@H]5[C@@H](O)[C@@H](CO)O[C@@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)C5O)[C@H](NC(C)=O)C4O[C@@H]4O[C@@H](C)[C@@H](O)[C@@H](O)C4O)[C@@H]3O)[C@H](NC(C)=O)[C@H]2O[C@@H]2O[C@H](CO)[C@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C52H88N2O39/c1-12-25(66)31(72)34(75)48(80-12)88-40-21(10-60)85-47(24(54-15(4)63)43(40)91-50-36(77)33(74)28(69)18(7-57)82-50)93-45-30(71)20(9-59)84-52(38(45)79)89-41-22(11-61)86-46(23(53-14(3)62)42(41)90-49-35(76)32(73)26(67)13(2)81-49)92-44-29(70)19(8-58)83-51(37(44)78)87-39(17(65)6-56)27(68)16(64)5-55/h5,12-13,16-52,56-61,64-79H,6-11H2,1-4H3,(H,53,62)(H,54,63)/t12-,13-,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+,42?,43+,44-,45?,46-,47-,48-,49-,50-,51-,52-/m0/s1 |
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InChI Key | BCUMESVDMXHZRL-JUDCGFFFSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as oligosaccharides. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. |
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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 | Oligosaccharides |
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Alternative Parents | |
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Substituents | - Oligosaccharide
- Fatty acyl glycoside
- N-acyl-alpha-hexosamine
- Alkyl glycoside
- Glycosyl compound
- O-glycosyl compound
- Beta-hydroxy aldehyde
- Fatty acyl
- Oxane
- Acetamide
- Alpha-hydroxyaldehyde
- Carboxamide group
- Secondary carboxylic acid amide
- Secondary alcohol
- Acetal
- Carboxylic acid derivative
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Hydrocarbon derivative
- Alcohol
- Organic oxide
- Carbonyl group
- Organopnictogen compound
- Aldehyde
- Primary alcohol
- Organic nitrogen compound
- 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 | splash10-0f6t-2869013000-288c6c3b26f893fd7e7e | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0gx4-6935022010-c14b9b7ff8c8a13c4905 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pcd-9843032000-f7124f35875877ee1d69 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000j-3139000110-4be0f7bdff91c366f3ee | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004j-4749003000-2a7306b716ed173dd7bc | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00b9-5732902201-62f29dc4ec803aea7e2c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-5795001000-aef44161f618d6f96e20 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0ldj-9658020010-d10c2081128dacd4450b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-05nb-9612034000-9b6fd9812897d7db7595 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-1339000000-8069fd1d1009b28756ae | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-08ms-5779000100-1bdf9dd2781c6fb3d27f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9100021000-cf48acc49cafe750ee3e | 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 | HMDB0006616 |
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FooDB ID | FDB024006 |
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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 | 35016014 |
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ChEBI ID | Not Available |
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PubChem Compound ID | 53477874 |
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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. Sabharwal, Hemant; Nilsson, Bo; Groenberg, Gunnar; Chester, M. Alan; Dakour, Jamal; Sjoeblad, Sture; Lundblad, Arne. Oligosaccharides from feces of preterm infants fed on breast milk. Archives of Biochemistry and Biophysics (1988), 265(2), 390-406. | 2. Yu H, Sipes JM, Cashel J, Bakos MA, Goldblum RM, Roberts DD: Recognition of type 1 chain oligosaccharides and lacto-series glycolipids by an antibody to human secretory component. Arch Biochem Biophys. 1995 Oct 1;322(2):299-305. | 3. Strecker G, Fievre S, Wieruszeski JM, Michalski JC, Montreuil J: Primary structure of four human milk octa-, nona-, and undeca-saccharides established by 1H- and 13C-nuclear magnetic resonance spectroscopy. Carbohydr Res. 1992 Mar 16;226(1):1-14. | 4. Forchielli ML, Walker WA: The role of gut-associated lymphoid tissues and mucosal defence. Br J Nutr. 2005 Apr;93 Suppl 1:S41-8. | 5. Yamashita K, Tachibana Y, Kobata A: Oligosaccharides of human milk. Structural studies of two new octasaccharides, difucosyl derivatives of para-lacto-N-hexaose and para-lacto-N-neohexaose. J Biol Chem. 1977 Aug 10;252(15):5408-11. | 6. LoCascio RG, Ninonuevo MR, Freeman SL, Sela DA, Grimm R, Lebrilla CB, Mills DA, German JB: Glycoprofiling of bifidobacterial consumption of human milk oligosaccharides demonstrates strain specific, preferential consumption of small chain glycans secreted in early human lactation. J Agric Food Chem. 2007 Oct 31;55(22):8914-9. Epub 2007 Oct 5. | 7. Kim HM, Kim IJ, Danishefsky SJ: Total syntheses of tumor-related antigens N3: probing the feasibility limits of the glycal assembly method. J Am Chem Soc. 2001 Jan 10;123(1):35-48. | 8. Bruntz R, Dabrowski U, Dabrowski J, Ebersold A, Peter-Katalinic J, Egge H: Fucose-containing oligosaccharides from human milk from a donor of blood group 0 Le(a) nonsecretor. Biol Chem Hoppe Seyler. 1988 Apr;369(4):257-73. |
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