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 15:12:19 UTC |
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Update Date | 2017-12-07 01:49:51 UTC |
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HMDB ID | HMDB0002923 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Isomaltose |
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Description | Isomaltose is a naturally occurring disaccharide composed of two glucose units in an alpha (1-6) glycosidic linkage. -- Pubchem. A deficiency of sucrase-isomaltase, an integral protein of the small intestine brush-border membrane responsible for catalyzing the hydrolysis of dietary sucrose and some of the products of starch digestion, results in osmotic diarrhea when the disaccharide is ingested, because absorption cannot occur until after hydrolysis produces the component monosaccharides. (OMIM 222800 ,). It is particularly suitable as a non-cariogenic sucrose replacement and is favorable in products for diabetics and prediabetic dispositions. --Wikipedia. |
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Structure | |
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Synonyms | Value | Source |
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(GLC)2 | ChEBI | 6-O-alpha-D-Glucopyranosyl-D-glucopyranose | ChEBI | alpha-D-GLC-(1->6)-D-GLC | ChEBI | alpha-D-GLCP-(1->6)-D-GLCP | ChEBI | alpha-D-Glucosyl-(1->6)-D-glucose | ChEBI | Brachiose | ChEBI | Hunterioside | ChEBI | 6-O-a-D-Glucopyranosyl-D-glucopyranose | Generator | 6-O-α-D-glucopyranosyl-D-glucopyranose | Generator | a-D-GLC-(1->6)-D-GLC | Generator | α-D-GLC-(1->6)-D-GLC | Generator | a-D-GLCP-(1->6)-D-GLCP | Generator | α-D-GLCP-(1->6)-D-GLCP | Generator | a-D-Glucosyl-(1->6)-D-glucose | Generator | α-D-glucosyl-(1->6)-D-glucose | Generator | 6-O-a-D-Glucopyranosyl-D-glucose | HMDB | 6-O-alpha-D-Glucopyranosyl-D-glucose | HMDB | 6-O-alpha-delta-Glucopyranosyl-delta-glucose | HMDB |
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Chemical Formula | C12H22O11 |
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Average Molecular Weight | 342.2965 |
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Monoisotopic Molecular Weight | 342.116211546 |
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IUPAC Name | (3R,4S,5S,6R)-6-({[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxane-2,3,4,5-tetrol |
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Traditional Name | brachiose |
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CAS Registry Number | 499-40-1 |
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SMILES | OC[C@H]1O[C@H](OC[C@H]2OC(O)[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/C12H22O11/c13-1-3-5(14)8(17)10(19)12(23-3)21-2-4-6(15)7(16)9(18)11(20)22-4/h3-20H,1-2H2/t3-,4-,5-,6-,7+,8+,9-,10-,11?,12+/m1/s1 |
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InChI Key | DLRVVLDZNNYCBX-RTPHMHGBSA-N |
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Chemical Taxonomy |
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Description | This compound belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. |
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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 | O-glycosyl compounds |
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Alternative Parents | |
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Substituents | - O-glycosyl compound
- Disaccharide
- Oxane
- Secondary alcohol
- Hemiacetal
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Acetal
- Hydrocarbon derivative
- Primary alcohol
- Alcohol
- 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 | Health effect: |
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Disposition | Source: Biological location: |
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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 | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0iu0-2695000000-b644ad8ee930f0244c0f | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-014i-4236229000-cc57f0250001605061e9 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-01ox-1709000000-e1aedea040f248898825 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-000i-9501000000-dfecff3e8858cc005d12 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-000i-9000000000-1e5c79ae513f06c8d563 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004l-0219000000-77abf6de9ff79d4ddfcf | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03fs-2915000000-70455c0b7e9dbd96c5b8 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ikd-6930000000-6466a054f554b370d893 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-3559000000-3d5899762c5229ad1bd0 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-03mi-4933000000-db46210de280609b14c2 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9520000000-c953abfa4f36a9b0b9e1 | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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General References | - Kuriyama M, Hiwatari R, Osame M, Igata A: Leucocyte alpha-1,4- and alpha-1,6-glucosidase activities towards oligosaccharides in late onset glycogenosis type II. Tohoku J Exp Med. 1990 Aug;161(4):343-51. [PubMed:2256108 ]
- Guddat S, Thevis M, Schanzer W: Identification and quantification of the plasma volume expander dextran in human urine by liquid chromatography-tandem mass spectrometry of enzymatically derived isomaltose. Biomed Chromatogr. 2005 Dec;19(10):743-50. [PubMed:15856492 ]
- Vitek V, Vitek K: Chromatography of sugars in body fluids. IV. Separation of isomaltose and lactose in urine by paper chromatography. Biochem Med. 1973 Feb;7(1):119-27. [PubMed:4684081 ]
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