| Record Information |
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| Version | 1.0 |
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| Creation date | 2015-10-09 22:31:17 UTC |
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| Update date | 2017-01-19 02:36:27 UTC |
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| FoodComEx ID | PC000545 |
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| FoodDB Record | FDB005660 |
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| Chemical Information |
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| Name | Udp-glucose |
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| Description | Uridine diphosphate glucose, also known as udpglucose or UDP-alpha-D-glucose, belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Uridine diphosphate glucose is an extremely weak basic (essentially neutral) compound (based on its pKa). Uridine diphosphate glucose exists in all living species, ranging from bacteria to humans. Within humans, uridine diphosphate glucose participates in a number of enzymatic reactions. In particular, galactose 1-phosphate and uridine diphosphate glucose can be biosynthesized from uridine diphosphategalactose and glucose 1-phosphate; which is catalyzed by the enzyme galactose-1-phosphate uridylyltransferase. In addition, uridine diphosphate glucose can be biosynthesized from uridine diphosphategalactose through its interaction with the enzyme UDP-glucose 4-epimerase. In humans, uridine diphosphate glucose is involved in galactose metabolism. Outside of the human body, Uridine diphosphate glucose has been detected, but not quantified in, several different foods, such as tea, ostrich ferns, chickpea, cinnamons, and sourdoughs. This could make uridine diphosphate glucose a potential biomarker for the consumption of these foods. |
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| CAS Number | 133-89-1 |
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| Structure | |
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| Synonyms | | Synonym | Source |
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| Udp glucose | biospider | | Udp-d-glucose | biospider | | Udp-delta-glucose | biospider | | Udp-GLC | biospider | | UDPG | biospider | | UPG | biospider | | Uridine 5'-(alpha-D-glucopyranosyl pyrophosphate) | biospider | | Uridine 5'-diphosphate glucose | biospider | | Uridine 5'-diphospho-a-D-glucose | biospider | | Uridine 5'-diphospho-alpha-D-glucose | biospider | | Uridine 5'-diphospho-alpha-delta-glucose | biospider | | Uridine 5'-diphosphoglucose | biospider | | Uridine 5'-pyrophosphate a-D-glucopyranosyl ester | biospider | | Uridine 5'-pyrophosphate a-delta-glucopyranosyl ester | biospider | | Uridine diphosphate glucose | biospider | | Uridine diphospho-d-glucose | biospider | | Uridine diphospho-delta-glucose | biospider | | Uridine diphosphoglucose | biospider | | Uridine pyrophosphate-glucose | biospider |
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| Chemical Formula | C15H24N2O17P2 |
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| IUPAC name | [({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid |
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| InChI Identifier | InChI=1S/C15H24N2O17P2/c18-3-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-4-6-9(21)11(23)13(31-6)17-2-1-7(19)16-15(17)25/h1-2,5-6,8-14,18,20-24H,3-4H2,(H,26,27)(H,28,29)(H,16,19,25)/t5-,6-,8-,9-,10+,11-,12-,13-,14-/m1/s1 |
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| InChI Key | HSCJRCZFDFQWRP-JZMIEXBBSA-N |
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| Isomeric SMILES | OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=CC(=O)NC2=O)[C@H](O)[C@@H](O)[C@@H]1O |
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| Average Molecular Weight | 566.3018 |
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| Monoisotopic Molecular Weight | 566.055020376 |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. |
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| Kingdom | Organic compounds |
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| Super Class | Nucleosides, nucleotides, and analogues |
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| Class | Pyrimidine nucleotides |
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| Sub Class | Pyrimidine nucleotide sugars |
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| Direct Parent | Pyrimidine nucleotide sugars |
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| Alternative Parents | |
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| Substituents | - Pyrimidine nucleotide sugar
- Pyrimidine ribonucleoside diphosphate
- Pentose phosphate
- Pentose-5-phosphate
- Glycosyl compound
- N-glycosyl compound
- Monosaccharide phosphate
- Organic pyrophosphate
- Pyrimidone
- Monoalkyl phosphate
- Hydropyrimidine
- Monosaccharide
- Organic phosphoric acid derivative
- Oxane
- Phosphoric acid ester
- Pyrimidine
- Alkyl phosphate
- Heteroaromatic compound
- Vinylogous amide
- Tetrahydrofuran
- Urea
- Secondary alcohol
- Lactam
- Polyol
- Oxacycle
- Organoheterocyclic compound
- Azacycle
- Organic nitrogen compound
- Hydrocarbon derivative
- Organic oxide
- Primary alcohol
- Alcohol
- Organonitrogen compound
- Organooxygen compound
- Organic oxygen compound
- Organopnictogen compound
- Aromatic heteromonocyclic compound
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| Molecular Framework | Aromatic heteromonocyclic compounds |
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| External Descriptors | |
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| Physico-Chemical Properties - Experimental |
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| Property | Value | Reference |
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| Experimental logP | Not Available | |
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| Experimental Water Solubility | Not Available | |
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| Melting Point | Not Available | |
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| Foods of Origin |
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| Food | Content Range | Average | Reference |
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| Food | | | Reference |
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| Production Data |
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| Production Method | commercial |
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| Production Method Reference | Not Available |
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| Production Method Reference File | Not Available |
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| Quantity Available | Production upon request, up to 15 mg |
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| Delivery Time | Not Available |
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| Storage Form | solid |
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| Storage Conditions | -80°C |
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| Stability | Not Available |
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| Purity | Not Available |
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| Spectra |
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| Spectral Data Upon Request | Not Available |
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| Provider Information |
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| Commercial Vendors |
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| Not Available |
