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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-22 15:12:41 UTC |
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Update Date | 2020-02-26 21:24:26 UTC |
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HMDB ID | HMDB0003213 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Raffinose |
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Description | Raffinose is a complex carbohydrate. It is a trisaccharide composed of galactose, fructose, and glucose. It can be found in beans, cabbage, brussels sprouts, broccoli, asparagus, other vegetables, and whole grains. Raffinose is hydrolyzed to D-galactose and sucrose by D-galactosidase (D-GAL). D-GAL also hydrolyzes other D-galactosides such as stachyose, verbascose, and galactinol [1-O-(D-galactosyl)-myoinositol], if present. The enzyme does not cleave linked galactose, as in lactose. Raffinose is also known as melitose and may be thought of as galactose and sucrose connected via an alpha(1->6) glycosidic linkage. Thus, raffinose can be broken down into galactose and sucrose via the enzyme alpha-galactosidase. Human intestines do not contain this enzyme (Wikipedia ). Raffinose is a trisaccharide occurring in Australian manna (from Eucalyptus spp, Myrtaceae) and in cottonseed meal (PubChem). |
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Structure | |
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Synonyms | Value | Source |
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6g-alpha-D-Galactosylsucrose | ChEBI | alpha-D-Galactopyranosyl-(1->6)-alpha-D-glucopyranosyl beta-D-fructofuranoside | ChEBI | alpha-D-Galp-(1->6)-alpha-D-GLCP-(12)-beta-D-fruf | ChEBI | Gossypose | ChEBI | Melitose | ChEBI | Melitriose | ChEBI | Rafinose | ChEBI | Raflinose | ChEBI | 6g-a-D-Galactosylsucrose | Generator | 6g-Α-D-galactosylsucrose | Generator | a-D-Galactopyranosyl-(1->6)-a-D-glucopyranosyl b-D-fructofuranoside | Generator | Α-D-galactopyranosyl-(1->6)-α-D-glucopyranosyl β-D-fructofuranoside | Generator | a-D-Galp-(1->6)-a-D-GLCP-(12)-b-D-fruf | Generator | Α-D-galp-(1->6)-α-D-GLCP-(12)-β-D-fruf | Generator | D-(+)-Raffinose | HMDB | D-Raffinose | HMDB | beta-D-Fructofuranosyl O-alpha-D-galactopyranosyl-(1→6)-alpha-D-glucopyranoside | HMDB | Β-D-fructofuranosyl O-α-D-galactopyranosyl-(1→6)-α-D-glucopyranoside | HMDB | Raffinose | HMDB |
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Chemical Formula | C18H32O16 |
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Average Molecular Weight | 504.4371 |
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Monoisotopic Molecular Weight | 504.169034976 |
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IUPAC Name | (2R,3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-3,4,5-triol |
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Traditional Name | raffinose |
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CAS Registry Number | 512-69-6 |
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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](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/C18H32O16/c19-1-5-8(22)11(25)13(27)16(31-5)30-3-7-9(23)12(26)14(28)17(32-7)34-18(4-21)15(29)10(24)6(2-20)33-18/h5-17,19-29H,1-4H2/t5-,6-,7-,8+,9-,10-,11+,12+,13-,14-,15+,16+,17-,18+/m1/s1 |
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InChI Key | MUPFEKGTMRGPLJ-ZQSKZDJDSA-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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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 80 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 203 mg/mL | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0i00-0984100000-9982c277f436fd7788a5 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 35V, positive | splash10-0a4o-0909000000-8e525d469d91c8d958cb | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive | splash10-004l-0229100000-0e86b420bc16a12fcb5a | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive | splash10-06vi-1529000000-ca7b5ce31b75cedc69b3 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive | splash10-0076-9430100000-a53bd43a032e7db1cb4d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT 40V, negative | splash10-00fr-0986000000-0bdcdaf84ed0bc932795 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 32V, negative | splash10-0uk9-7930060000-ac8500ed18415634b666 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QFT , negative | splash10-0kp0-9820010000-016241d403acb7b8c491 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative | splash10-004i-0090000000-b2481c83084387e12838 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - QqQ 12V, negative | splash10-0udi-0100090000-6da14a924bf87e052d40 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - QqQ 19V, negative | splash10-0fb9-2910030000-27a02c65bb1897d0b234 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - QqQ 25V, negative | splash10-002r-6910000000-a9a928caa280abfbd94d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - QqQ 30V, negative | splash10-000i-9710000000-49017cc7d06a2393eab3 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 20V, negative | splash10-0udi-0000090000-2f07c4e073c08b44cbc6 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 22V, negative | splash10-0udi-0200090000-48ca69a647f8a160cfcf | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 25V, negative | splash10-0udi-2611090000-02d0b16ed861ce2e2251 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 30V, negative | splash10-0ug0-4910020000-75edd90b36765151b923 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 37V, negative | splash10-0079-9820000000-163d92c370b7f8085dc9 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 45V, negative | splash10-0kmr-9510000000-b6c552ccce26ade9d72c | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Orbitrap 55V, negative | splash10-05g0-9300000000-7eeb9c4ff5f74d594a40 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01q9-0901000000-0da93ae66a255c539613 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03gi-0905000000-b14ef3fbf37ecca83a6b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03dl-9800000000-07dcde9d0cb5481f432b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-2901000000-f86191b929c7806ddd56 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03fr-0900000000-e4a2b4341d424cbea7d0 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-002e-6910000000-5d77ce1936f86d2012fe | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 4.8 +/- 5.4 uM | Adult (>18 years old) | Male | Normal | | details | Feces | Detected but not Quantified | Not Quantified | Infant (0-1 year old) | Both | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | Not Quantified | Newborn (0-30 days old) | Both | Sepsis | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Colorectal Cancer | | details |
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Associated Disorders and Diseases |
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Disease References | Colorectal cancer |
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- Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
| Sepsis |
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- Stewart CJ, Embleton ND, Marrs ECL, Smith DP, Fofanova T, Nelson A, Skeath T, Perry JD, Petrosino JF, Berrington JE, Cummings SP: Longitudinal development of the gut microbiome and metabolome in preterm neonates with late onset sepsis and healthy controls. Microbiome. 2017 Jul 12;5(1):75. doi: 10.1186/s40168-017-0295-1. [PubMed:28701177 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | C00001145 |
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Chemspider ID | Not Available |
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KEGG Compound ID | C00492 |
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BioCyc ID | CPD-1099 |
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BiGG ID | Not Available |
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Wikipedia Link | Raffinose |
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METLIN ID | Not Available |
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PubChem Compound | 439242 |
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PDB ID | Not Available |
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ChEBI ID | 16634 |
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Food Biomarker Ontology | Not Available |
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VMH ID | RAFFIN |
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MarkerDB ID | |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Toussaint M, Latger-Cannard V, Caron A, Lecompte T, Vigneron C, Menu P: Hemoglobin-based oxygen carriers do not alter platelet functions: study of three chemically modified hemoglobin solutions. Intensive Care Med. 2003 Jan;29(1):62-8. Epub 2002 Nov 30. [PubMed:12528024 ]
- Gross KC, Houghton MP, Senterfit LB: Presumptive speciation of Streptococcus bovis and other group D streptococci from human sources by using arginine and pyruvate tests. J Clin Microbiol. 1975 Jan;1(1):54-60. [PubMed:1176592 ]
- Xue S, Paterson W, Valdez D, Miller D, Christoff B, Wong LT, Diamant NE: Effect of an o-raffinose cross-linked haemoglobin product on oesophageal and lower oesophageal sphincter motor function. Neurogastroenterol Motil. 1999 Dec;11(6):421-30. [PubMed:10583849 ]
- Persson AE, Schnermann J, Agerup B, Eriksson NE: The hydraulic conductivity of the rat proximal tubular wall determined with colloidal solutions. Pflugers Arch. 1975 Oct 16;360(1):25-44. [PubMed:1237863 ]
- Lobley RW, Burrows PC, Warwick R, Dawson DJ, Holmes R: Simultaneous assessment of intestinal permeability and lactose tolerance with orally administered raffinose, lactose and L-arabinose. Clin Sci (Lond). 1990 Aug;79(2):175-83. [PubMed:2167807 ]
- Rodrigues Silva C, Dutra de Oliveira JE, de Souza RA, Silva HC: Effect of a rice bran fiber diet on serum glucose levels of diabetic patients in Brazil. Arch Latinoam Nutr. 2005 Mar;55(1):23-7. [PubMed:16187674 ]
- Hessels J, Snoeyink EJ, Platenkamp AJ, Voortman G, Steggink J, Eidhof HH: Assessment of intestinal permeability: enzymatic determination of urinary mannitol, raffinose, sucrose and lactose on Hitachi analyzer. Clin Chem Lab Med. 2003 Jan;41(1):33-8. [PubMed:12636047 ]
- Horodniceanu T, Delbos F: [Group D streptococci in human infections: identification and sensitivity to antibiotics (author's transl)]. Ann Microbiol (Paris). 1980 Sep-Oct;131B(2):131-44. [PubMed:7458116 ]
- Lieberthal W, Fuhro R, Alam H, Rhee P, Szebeni J, Hechtman HB, Favuzza J, Veech RL, Valeri CR: Comparison of the effects of a 50% exchange-transfusion with albumin, hetastarch, and modified hemoglobin solutions. Shock. 2002 Jan;17(1):61-9. [PubMed:11795671 ]
- Gundermann KJ, Lie TS: Problems of competition in charcoal hemoperfusion for the treatment of intoxications. Artif Organs. 1979 Nov;3(4):346-9. [PubMed:533425 ]
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