Record Information |
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Version | 1.0 |
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Creation date | 2010-04-08 22:06:47 UTC |
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Update date | 2020-09-17 15:38:32 UTC |
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Primary ID | FDB005660 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB 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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GLUCOSE-uridine-C1,5'-diphosphATE | ChEBI | UDP-D-Glucose | ChEBI | UDPglucose | ChEBI | URIDINE-5'-diphosphATE-glucose | ChEBI | UDP-alpha-D-Glucose | Kegg | GLUCOSE-uridine-C1,5'-diphosphoric acid | Generator | URIDINE-5'-diphosphoric acid-glucose | Generator | UDP-a-D-Glucose | Generator | UDP-Α-D-glucose | Generator | Uridine diphosphoric acid glucose | Generator | Diphosphate glucose, uridine | HMDB | Diphosphoglucose, uridine | HMDB | Glucose, UDP | HMDB | Glucose, uridine diphosphate | HMDB | UDP Glucose | HMDB | UDPG | HMDB | Uridine diphosphoglucose | HMDB | UDP-GLC | HMDB | UDP-Glucose | HMDB | Uridine 5'-(alpha-D-glucopyranosyl pyrophosphate) | HMDB | Uridine 5'-(α-D-glucopyranosyl pyrophosphate) | HMDB | Uridine 5'-diphosphate glucose | HMDB | Uridine 5'-diphospho-alpha-D-glucose | HMDB | Uridine 5'-diphospho-α-D-glucose | HMDB | Uridine 5'-diphosphoglucose | HMDB | Uridine 5’-(α-D-glucopyranosyl pyrophosphate) | HMDB | Uridine 5’-diphosphate glucose | HMDB | Uridine 5’-diphospho-α-D-glucose | HMDB | Uridine 5’-diphosphoglucose | HMDB | Uridine diphospho-D-glucose | HMDB | Uridine pyrophosphate-glucose | HMDB | Uridine diphosphate glucose | ChEBI | Udp glucose | biospider | Udp-d-glucose | biospider | Udp-delta-glucose | biospider | Udp-GLC | biospider | UPG | biospider | Uridine 5'-diphospho-a-D-glucose | biospider | Uridine 5'-diphospho-alpha-delta-glucose | biospider | Uridine 5'-pyrophosphate a-D-glucopyranosyl ester | biospider | Uridine 5'-pyrophosphate a-delta-glucopyranosyl ester | biospider | Uridine diphospho-d-glucose | biospider | Uridine diphospho-delta-glucose | biospider |
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Predicted Properties | |
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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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Classification |
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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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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Role | Industrial application: |
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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 | Not Available | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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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 | Not Available | |
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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 | Type | Description | Splash Key | View |
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Predicted GC-MS | Udp-glucose, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-054k-3933570000-89f658b2d26ff158d84c | Spectrum | Predicted GC-MS | Udp-glucose, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0fk9-4942706000-3a83736296429f83adee | Spectrum | Predicted GC-MS | Udp-glucose, "Uridine diphosphate glucose,1TMS,#1" TMS, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_1_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_1_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_1_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_2_12, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_2_13, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum | Predicted GC-MS | Udp-glucose, TMS_2_14, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated) | splash10-014i-0000090000-1692ab5f5dad1cf7e436 | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated) | splash10-015a-0439510000-69e7cd4c2c365a24706b | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated) | splash10-0109-5753970000-03f34041208ba93ef87a | Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-00fr-9257000000-73b85a465d99ce92467d | Spectrum | MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-00ba-9333000000-b57dc1340555f1a997b4 | Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-00fr-9257000000-ba1e6c754b8f04d5b659 | Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Positive | splash10-0002-9000000000-9bd63595c19dbe18d143 | Spectrum | MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0009000000-4b94aa10fd96d2d9c505 | Spectrum | MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0009000000-996cd4acdaa34c877460 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0901110000-4b81825405869909992e | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-3911000000-6fd09254750e77963110 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-5900000000-03a2a98eb0aa84737530 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-03di-4901260000-8396a090c14de7f2d708 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01ox-8907020000-94410556a0288cb8167b | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-06tf-5901000000-10132c85ad33464d4eef | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00kr-0000960000-6404d8d944e1ae6f30e2 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-07e1-2322960000-6af539ce21752f9023ba | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-08fr-9732000000-b0c81adc41b1d799e1e8 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-014i-0000090000-8cab8f2bc0fb9e9e8ba9 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-057j-9203870000-d60681ff91f741bdb867 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-3519000000-67ca2f9355ef7f94a47d | Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | Not Available |
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ChEMBL ID | Not Available |
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KEGG Compound ID | Not Available |
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Pubchem Compound ID | 8629 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 18066 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | DB01861 |
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HMDB ID | HMDB00286 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | UDP-GLUCOSE |
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BIGG ID | Not Available |
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KNApSAcK ID | C00001514 |
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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 | Uridine diphosphate glucose |
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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 | Not Available |
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Enzymes | Not Available |
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Pathways | Not Available |
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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).
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