| Record Information |
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| Version | 1.0 |
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| Creation Date | 2016-09-30 22:47:50 UTC |
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| Update Date | 2020-06-04 20:50:42 UTC |
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| BMDB ID | BMDB0001586 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | Glucose 1-phosphate |
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| Description | Galactose 1-phosphate, also known as delta-glucose 1-phosphate or cori ester, belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. Galactose 1-phosphate is possibly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Galactose 1-phosphate exists in all living species, ranging from bacteria to humans. Galactose 1-phosphate participates in a number of enzymatic reactions, within cattle. In particular, Uridine diphosphate glucose and galactose 1-phosphate can be biosynthesized from uridine diphosphategalactose and glucose 1-phosphate through its interaction with the enzyme galactose-1-phosphate uridylyltransferase. Furthermore, Galactose 1-phosphate can be biosynthesized from D-galactose through the action of the enzyme galactokinase. Finally, Uridine diphosphate glucose and galactose 1-phosphate can be biosynthesized from uridine diphosphategalactose and glucose 1-phosphate; which is mediated by the enzyme galactose-1-phosphate uridylyltransferase. In cattle, galactose 1-phosphate is involved in a couple of metabolic pathways, which include the nucleotide sugars metabolism pathway and lactose synthesis pathway. Galactose 1-phosphate is a potentially toxic compound. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 1-O-Phosphono-D-glucopyranose | ChEBI | | Cori ester | ChEBI | | D-Glucose 1-phosphate | ChEBI | | GLC-1-p | ChEBI | | D-Glucose 1-phosphoric acid | Generator | | Glucose 1-phosphoric acid | Generator | | a-D-Glucopyranosyl phosphate | HMDB | | a-D-Glucose 1-phosphate | HMDB | | alpha-D-Glucopyranosyl phosphate | HMDB | | alpha-D-Glucose 1-phosphate | HMDB | | alpha-D-Glucose-1-phosphate | HMDB | | alpha-delta-Glucopyranosyl phosphate | HMDB | | alpha-delta-Glucose 1-phosphate | HMDB | | alpha-delta-Glucose-1-phosphate | HMDB | | D-Glucopyranose 1-phosphate | HMDB | | D-Glucose-1-p | HMDB | | D-Glucose-1-phosphate | HMDB | | delta-Glucopyranose 1-phosphate | HMDB | | delta-Glucose 1-phosphate | HMDB | | delta-Glucose-1-p | HMDB | | delta-Glucose-1-phosphate | HMDB | | Glucose monophosphate | HMDB | | Glucose-1-phosphate | HMDB | | Glucose-1P | HMDB | | Galactose 1-phosphoric acid | HMDB |
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| Chemical Formula | C6H13O9P |
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| Average Molecular Weight | 260.1358 |
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| Monoisotopic Molecular Weight | 260.029718526 |
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| IUPAC Name | {[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phosphonic acid |
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| Traditional Name | glucose 1-phosphate |
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| CAS Registry Number | 59-56-3 |
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| SMILES | OC[C@H]1OC(OP(O)(O)=O)[C@H](O)[C@@H](O)[C@@H]1O |
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| InChI Identifier | InChI=1S/C6H13O9P/c7-1-2-3(8)4(9)5(10)6(14-2)15-16(11,12)13/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6?/m1/s1 |
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| InChI Key | HXXFSFRBOHSIMQ-GASJEMHNSA-N |
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| Chemical Taxonomy |
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| Description | belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit. |
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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 | Monosaccharide phosphates |
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| Alternative Parents | |
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| Substituents | - Hexose monosaccharide
- Monosaccharide phosphate
- Monoalkyl phosphate
- Organic phosphoric acid derivative
- Oxane
- Alkyl phosphate
- Phosphoric acid ester
- Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Alcohol
- Hydrocarbon derivative
- Primary alcohol
- Organic oxide
- 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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| Status | Detected and Quantified |
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| Origin | |
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| Biofunction | Not Available |
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| Application | Not Available |
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| Cellular locations | |
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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 | 1000.0 mg/mL | Not Available | | LogP | Not Available | Not Available |
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| Predicted Properties | |
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| Spectra |
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| Spectra | |
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| Biological Properties |
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| Cellular Locations | |
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| Biospecimen Locations | - Fibroblasts
- Longissimus Thoracis Muscle
- Mammary Gland
- Milk
- Muscle
- Semimembranosus Muscle
- Urine
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| Pathways | |
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| Normal Concentrations |
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| Fibroblasts | Expected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Longissimus Thoracis Muscle | Detected and Quantified | 184 +/- 58 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Mammary Gland | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 52.60 +/- 27.92 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 3.844 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 58 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 43 +/- 3 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 43 +/- 11 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 55 +/- 3 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 55 +/- 3 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 58 +/- 2 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 86.70 +/- 128.89 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 43 +/- 3 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 43 +/- 11 uM | Not Specified | Not Specified | Normal | | details | | Milk | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details | | Milk | Detected and Quantified | 28.31 +/- 27.81 uM | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 363-1178 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Muscle | Detected and Quantified | 120 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Semimembranosus Muscle | Detected and Quantified | 175 +/- 48 nmol/g of tissue | Not Specified | Not Specified | Normal | | details | | Urine | Detected but not Quantified | Not Quantified | Not Specified | Not Specified | Normal | | details |
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| Abnormal Concentrations |
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| Not Available |
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| External Links |
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| HMDB ID | HMDB0001586 |
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| DrugBank ID | Not Available |
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| Phenol Explorer Compound ID | Not Available |
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| FooDB ID | FDB001159 |
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| KNApSAcK ID | Not Available |
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| Chemspider ID | 388311 |
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| KEGG Compound ID | C00103 |
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| BioCyc ID | D-glucose-1-phosphates |
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| BiGG ID | 33865 |
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| Wikipedia Link | Glucose-1-phosphate |
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| METLIN ID | 6331 |
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| PubChem Compound | 439165 |
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| PDB ID | Not Available |
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| ChEBI ID | 16077 |
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| References |
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| Synthesis Reference | Weinhausel, Andreas; Nidetzky, Bernd; Kysela, Christian; Kulbe, Klaus D. Application of Escherichia coli maltodextrin-phosphorylase for the continuous production of glucose-1-phosphate. Enzyme and Microbial Technology (1995), 17(2), 140-6. |
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| Material Safety Data Sheet (MSDS) | Not Available |
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| General References | - Sundekilde UK, Gustavsson F, Poulsen NA, Glantz M, Paulsson M, Larsen LB, Bertram HC: Association between the bovine milk metabolome and rennet-induced coagulation properties of milk. J Dairy Sci. 2014 Oct;97(10):6076-84. doi: 10.3168/jds.2014-8304. Epub 2014 Jul 30. [PubMed:25087032 ]
- Buitenhuis AJ, Sundekilde UK, Poulsen NA, Bertram HC, Larsen LB, Sorensen P: Estimation of genetic parameters and detection of quantitative trait loci for metabolites in Danish Holstein milk. J Dairy Sci. 2013 May;96(5):3285-95. doi: 10.3168/jds.2012-5914. Epub 2013 Mar 15. [PubMed:23497994 ]
- O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
- Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
- A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
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