Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:10:06 UTC |
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Update date | 2019-11-26 03:06:34 UTC |
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Primary ID | FDB012320 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Stachyose |
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Description | Isolated from soybean meal (Glycine max), tubers of Japanese artichoke (Stachys tubifera) and lentils
Stachyose is a tetrasaccharide consisting of two D-galactose units, one D-glucose unit, and one D-fructose unit sequentially linked. Stachyose is a normal human metabolite present in human milk and is naturally found in many vegetables (e.g. green beans, soybeans and other beans) and plants. The glycosylation of serum transferrin from galactosemic patients with a deficiency of galactose-1-phosphate uridyl transferase (EC 2. 7.7 12) is abnormal but becomes normal after treatment with a galactose-free diet. Adhering to a galactose-free diet by strictly avoiding dairy products and known hidden sources of galactose does not completely normalize galactose-1-phosphate (gal-1-P) in erythrocytes from patients with galactosemia, since galactose released from stachyose may be absorbed and contribute to elevated gal-1-P values in erythrocytes of galactosemic patients. (PMID: 7671975, 9499382); Stachyose is a tetrasaccharide consisting of two ?-D-galactose units, one ?-D-glucose unit, and one ?-D-fructose unit sequentially linked as gal(?1?6)gal(?1?6)glc(?1?2?)fru. Stachyose is naturally found in numerous vegetables (e.g. green beans, soybeans and other beans) and plants. |
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CAS Number | 470-55-3 |
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Structure | |
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Synonyms | Synonym | Source |
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a-D-Galp-(1->6)-a-D-galp-(1->6)-a-D-glcp-(12)-b-D-fruf | Generator | alpha-D-Galp-(1->6)-alpha-D-galp-(1->6)-alpha-D-glcp-(12)-beta-D-fruf | ChEBI | b-D-Fructofuranosyl O-a-D-galactopyranosyl-(1->6)-O-a-D-galactopyranosyl-(1->6)-a-D-glucopyranoside, 9CI, 8CI | db_source | b-Galactan | db_source | beta-D-Fructofuranosyl O-alpha-D-galactopyranosyl-(1->6)-O-alpha-D-galactopyranosyl-(1->6)-alpha-D-glucopyranoside | HMDB | Cicerose | db_source | D-stachyose | biospider | Lupeose | db_source | Manneotetrose | db_source | O-a-D-Galactopyranosyl-(1->6)O-a-D-galactopyranosyl-(1->6)O-a-D-galactopyranosyl-b-D-fructofuranoside | Generator | O-alpha-D-Galactopyranosyl-(1->6)O-alpha-D-galactopyranosyl-(1->6)O-alpha-D-galactopyranosyl-beta-D-fructofuranoside | ChEBI | O-α-D-galactopyranosyl-(1->6)O-α-D-galactopyranosyl-(1->6)O-α-D-galactopyranosyl-β-D-fructofuranoside | Generator | α-D-galp-(1->6)-α-D-galp-(1->6)-α-D-glcp-(12)-β-D-fruf | Generator |
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Predicted Properties | |
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Chemical Formula | C24H42O21 |
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IUPAC name | 2-({6-[(6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methoxy]-3,4,5-trihydroxyoxan-2-yl}methoxy)-6-(hydroxymethyl)oxane-3,4,5-triol |
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InChI Identifier | InChI=1S/C24H42O21/c25-1-6-10(28)14(32)17(35)21(41-6)39-3-8-11(29)15(33)18(36)22(42-8)40-4-9-12(30)16(34)19(37)23(43-9)45-24(5-27)20(38)13(31)7(2-26)44-24/h6-23,25-38H,1-5H2 |
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InChI Key | UQZIYBXSHAGNOE-UHFFFAOYSA-N |
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Isomeric SMILES | OCC1OC(CO)(OC2OC(COC3OC(COC4OC(CO)C(O)C(O)C4O)C(O)C(O)C3O)C(O)C(O)C2O)C(O)C1O |
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Average Molecular Weight | 666.5777 |
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Monoisotopic Molecular Weight | 666.221858406 |
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Classification |
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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
- C-glycosyl compound
- Glycosyl compound
- O-glycosyl compound
- Ketal
- Oxane
- Tetrahydrofuran
- Secondary alcohol
- Acetal
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Alcohol
- Primary alcohol
- Hydrocarbon derivative
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Ontology | No ontology term |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | C 43.25%; H 6.35%; O 50.40% | DFC |
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Melting Point | Mp 167-170° (anhyd.) | DFC |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | [a]23D +131.3 (c, 4.5 in H2O) | DFC |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Not Available |
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MS/MS | Type | Description | Splash Key | View |
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Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01q9-0900000000-9051231e83f301a09a0e | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03ei-0902300000-1d2431079f0fcf16f362 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03dl-9800000000-9f5834420ffbcf1d03e5 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-2900001000-1b21dc3904103d99d080 | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01t9-1900000000-92c5416ad039dfd6ec6b | 2015-05-27 | View Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-002e-6911000000-f2c6489ad24930392c3e | 2015-05-27 | View Spectrum |
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NMR | Not Available |
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External Links |
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ChemSpider ID | 388624 |
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ChEMBL ID | CHEMBL1625803 |
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KEGG Compound ID | C01613 |
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Pubchem Compound ID | 439531 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 17164 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB03553 |
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CRC / DFC (Dictionary of Food Compounds) ID | HGH56-Q:HGH56-Q |
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EAFUS ID | Not Available |
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Dr. Duke ID | STACHYOSE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00001150 |
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HET ID | Not Available |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Stachyose |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | |
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Enzymes | Name | Gene Name | UniProt ID |
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Alpha-galactosidase A | GLA | P06280 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | — Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004). — Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
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