Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2006-08-12 23:36:48 UTC |
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Update Date | 2021-10-13 04:41:59 UTC |
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HMDB ID | HMDB0003553 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Stachyose |
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Description | 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 ). |
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Structure | OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO[C@H]3O[C@H](CO[C@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O 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/t6-,7-,8-,9-,10+,11+,12-,13-,14+,15+,16+,17-,18-,19-,20+,21+,22+,23-,24+/m1/s1 |
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Synonyms | Value | Source |
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alpha-D-Galp-(1->6)-alpha-D-galp-(1->6)-alpha-D-GLCP-(12)-beta-D-fruf | ChEBI | O-alpha-D-Galactopyranosyl-(1->6)O-alpha-D-galactopyranosyl-(1->6)O-alpha-D-galactopyranosyl-beta-D-fructofuranoside | ChEBI | a-D-Galp-(1->6)-a-D-galp-(1->6)-a-D-GLCP-(12)-b-D-fruf | Generator | Α-D-galp-(1->6)-α-D-galp-(1->6)-α-D-GLCP-(12)-β-D-fruf | Generator | O-a-D-Galactopyranosyl-(1->6)O-a-D-galactopyranosyl-(1->6)O-a-D-galactopyranosyl-b-D-fructofuranoside | Generator | O-Α-D-galactopyranosyl-(1->6)O-α-D-galactopyranosyl-(1->6)O-α-D-galactopyranosyl-β-D-fructofuranoside | Generator | beta-D-Fructofuranosyl O-alpha-D-galactopyranosyl-(1->6)-O-alpha-D-galactopyranosyl-(1->6)-alpha-D-glucopyranoside | HMDB | D-Stachyose | HMDB | Β-D-fructofuranosyl O-α-D-galactopyranosyl-(1→6)-O-α-D-galactopyranosyl-(1→6)-α-D-glucopyranoside | HMDB | Stachyose | HMDB |
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Chemical Formula | C24H42O21 |
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Average Molecular Weight | 666.5777 |
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Monoisotopic Molecular Weight | 666.221858406 |
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IUPAC Name | (2S,3R,4S,5R,6R)-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4S,5R,6R)-6-{[(2S,3S,4S,5R)-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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Traditional Name | (2S,3R,4S,5R,6R)-2-{[(2R,3R,4S,5R,6S)-6-{[(2R,3S,4S,5R,6R)-6-{[(2S,3S,4S,5R)-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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CAS Registry Number | 470-55-3 |
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SMILES | OC[C@H]1O[C@@](CO)(O[C@H]2O[C@H](CO[C@H]3O[C@H](CO[C@H]4O[C@H](CO)[C@H](O)[C@H](O)[C@H]4O)[C@H](O)[C@H](O)[C@H]3O)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@@H]1O |
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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/t6-,7-,8-,9-,10+,11+,12-,13-,14+,15+,16+,17-,18-,19-,20+,21+,22+,23-,24+/m1/s1 |
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InChI Key | UQZIYBXSHAGNOE-XNSRJBNMSA-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
- 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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Physiological effect | Not Available |
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Disposition | |
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Process | |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (Non-derivatized) - 70eV, Positive | splash10-0k9b-5402129000-61642294535e87144940 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_1_4) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_1_5) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_1_6) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_1_7) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_1_8) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_1_9) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_1_10) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_1_11) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_1_12) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_1_13) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_1_14) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_2_4) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_2_5) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_2_6) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_2_7) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_2_8) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_2_9) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Stachyose GC-MS (TMS_2_10) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental LC-MS/MS | LC-MS/MS Spectrum - Stachyose Quattro_QQQ 10V, Positive-QTOF (Annotated) | splash10-014i-0000009000-d94a236a9a5a6bd5c972 | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Stachyose Quattro_QQQ 25V, Positive-QTOF (Annotated) | splash10-017i-1828209000-9199e7c55d37d011eac1 | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Stachyose Quattro_QQQ 40V, Positive-QTOF (Annotated) | splash10-000i-7912000000-8a80b033b9a4ea01bc8e | 2012-07-25 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Stachyose 35V, Negative-QTOF | splash10-00ar-7915000000-788f6809791936fee494 | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Stachyose 10V, Negative-QTOF | splash10-014i-0000009000-e38a72ceefebbe0bb3da | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Stachyose 40V, Negative-QTOF | splash10-0040-4915000000-fba1f7d256aa66bf110e | 2021-09-20 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Stachyose 20V, Negative-QTOF | splash10-014i-0101009000-c01c60a83d955171e974 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Stachyose 10V, Positive-QTOF | splash10-01q9-0900000000-9a4d05616e9796aaf3a5 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Stachyose 20V, Positive-QTOF | splash10-03ei-0902200000-8724dec2357b4a940fed | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Stachyose 40V, Positive-QTOF | splash10-03dl-8900000000-8bb4399ade337d2bf2e0 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Stachyose 10V, Negative-QTOF | splash10-03di-2900001000-02f4bb852a9d5309ddf5 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Stachyose 20V, Negative-QTOF | splash10-01t9-1900000000-0f98c8c4de6b8e4eea1e | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Stachyose 40V, Negative-QTOF | splash10-002e-5910000000-10e95551d72e06a4af9b | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Stachyose 10V, Positive-QTOF | splash10-02u1-0703129000-d54a2da09fac24cd6697 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Stachyose 20V, Positive-QTOF | splash10-0lxt-3900012000-690517e60a43f657f5e8 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Stachyose 40V, Positive-QTOF | splash10-052e-9402110000-47e64f8f36cdc20b3a22 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Stachyose 10V, Negative-QTOF | splash10-02ti-0500329000-3cc0bae4bdfdb007458f | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Stachyose 20V, Negative-QTOF | splash10-0a4i-9300155000-4c88b7187013b314fab9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Stachyose 40V, Negative-QTOF | splash10-004l-9400010000-76e554af98beaaf0d8f5 | 2021-09-24 | Wishart Lab | View Spectrum |
NMR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Experimental 1D NMR | 1H NMR Spectrum (1D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Predicted 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | 2021-09-24 | Wishart Lab | View Spectrum | Experimental 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental) | 2012-12-05 | Wishart Lab | View Spectrum |
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General References | - Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- Sandrin MS, Vaughan HA, Dabkowski PL, McKenzie IF: Anti-pig IgM antibodies in human serum react predominantly with Gal(alpha 1-3)Gal epitopes. Proc Natl Acad Sci U S A. 1993 Dec 1;90(23):11391-5. [PubMed:7504304 ]
- Wiesmann UN, Rose-Beutler B, Schluchter R: Leguminosae in the diet: the raffinose-stachyose question. Eur J Pediatr. 1995;154(7 Suppl 2):S93-6. [PubMed:7671975 ]
- Charlwood J, Clayton P, Keir G, Mian N, Winchester B: Defective galactosylation of serum transferrin in galactosemia. Glycobiology. 1998 Apr;8(4):351-7. [PubMed:9499382 ]
- (). Lewis blood groups of breastfeeding women tested serologically and by chromatographic analysis of human milk oligosaccharides. Thurl, S., Henker, J., Siegel, M., Tovar, K., Sawatzki, G. Milchwissenschaft (1998), 53(3), 127-129. Publisher: VV-GmbH Volkswirtschaftlicher Verlag, CODEN: MILCAD ISSN: 0026-3788. .
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