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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 | 2005-11-16 15:48:42 UTC |
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Update Date | 2020-05-12 18:46:58 UTC |
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HMDB ID | HMDB0000218 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Orotidylic acid |
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Description | Orotidylic acid, also known as orotidylate or 5'-OMP, belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety. Orotidylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Orotidylic acid exists in all living species, ranging from bacteria to humans. guanidoacetic acid and orotidylic acid can be biosynthesized from glycine and L-arginine; which is catalyzed by the enzyme glycine amidinotransferase, mitochondrial. In humans, orotidylic acid is involved in the metabolic disorder called the dimethylglycine dehydrogenase deficiency pathway. Outside of the human body, Orotidylic acid has been detected, but not quantified in, several different foods, such as parsley, common persimmons, other bread, oriental wheats, and custard apples. This could make orotidylic acid a potential biomarker for the consumption of these foods. A pyrimidine ribonucleoside 5'-monophosphate having 6-carboxyuracil as the nucleobase. |
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Structure | |
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Synonyms | Value | Source |
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6-Carboxy-5'-uridylic acid | ChEBI | Orotidine 5'-(dihydrogen phosphate) | ChEBI | 6-Carboxy-5'-uridylate | Generator | Orotidine 5'-(dihydrogen phosphoric acid) | Generator | Orotidylate | Generator | 1,2,3,6-Tetrahydro-2,6-dioxo-3-(5-O-phosphono-b-D-ribofuranosyl)-4-pyrimidinecarboxylate | HMDB | 1,2,3,6-Tetrahydro-2,6-dioxo-3-(5-O-phosphono-b-D-ribofuranosyl)-4-pyrimidinecarboxylic acid | HMDB | 1,2,3,6-Tetrahydro-2,6-dioxo-3-(5-O-phosphono-beta-delta-ribofuranosyl)-4-pyrimidinecarboxylate | HMDB | 1,2,3,6-Tetrahydro-2,6-dioxo-3-(5-O-phosphono-beta-delta-ribofuranosyl)-4-pyrimidinecarboxylic acid | HMDB | 2,6-Dioxo-3-(5-O-phosphono-beta-D-ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid | HMDB | 2,6-Dioxo-3-(5-O-phosphono-beta-delta-ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid | HMDB | 5'-(Dihydrogen phosphate) 6-carboxy-uridine | HMDB | 5'-(Dihydrogen phosphate) orotidine | HMDB | 5'-OMP | HMDB | 5'-Phosphate orotidine | HMDB | 5-(Dihydrogen phosphate)orotidine | HMDB | Ometoprim | HMDB | OMP | HMDB | Omp (nucleotide) | HMDB | Orotidine 5'-monophosphate | HMDB | Orotidine 5'-phosphate | HMDB | Orotidine monophosphate | HMDB | Orotidine-5'-phosphate | HMDB | 1,2,3,6-Tetrahydro-2,6-dioxo-3-(5-O-phosphono-beta-D-ribofuranosyl)-4-pyrimidinecarboxylic acid | HMDB | 1,2,3,6-Tetrahydro-2,6-dioxo-3-(5-O-phosphono-β-D-ribofuranosyl)-4-pyrimidinecarboxylic acid | HMDB | 5’-OMP | HMDB | Orotidine 5’-monophosphate | HMDB | Orotidylic acid | HMDB |
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Chemical Formula | C10H13N2O11P |
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Average Molecular Weight | 368.1908 |
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Monoisotopic Molecular Weight | 368.02569578 |
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IUPAC Name | 3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid |
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Traditional Name | 6-carboxy-5'-uridylic acid |
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CAS Registry Number | 2149-82-8 |
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SMILES | O[C@H]1[C@@H](O)[C@@H](O[C@@H]1COP(O)(O)=O)N1C(=O)NC(=O)C=C1C(O)=O |
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InChI Identifier | InChI=1S/C10H13N2O11P/c13-5-1-3(9(16)17)12(10(18)11-5)8-7(15)6(14)4(23-8)2-22-24(19,20)21/h1,4,6-8,14-15H,2H2,(H,16,17)(H,11,13,18)(H2,19,20,21)/t4-,6-,7-,8-/m1/s1 |
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InChI Key | KYOBSHFOBAOFBF-XVFCMESISA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as pyrimidine ribonucleoside monophosphates. These are pyrimidine ribobucleotides with monophosphate group linked to the ribose moiety. |
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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 ribonucleotides |
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Direct Parent | Pyrimidine ribonucleoside monophosphates |
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Alternative Parents | |
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Substituents | - Pyrimidine ribonucleoside monophosphate
- Pentose-5-phosphate
- Pentose phosphate
- Glycosyl compound
- N-glycosyl compound
- Monosaccharide phosphate
- Pentose monosaccharide
- Pyrimidine-6-carboxylic acid or derivatives
- Pyrimidine-6-carboxylic acid
- Hydropyrimidine carboxylic acid derivative
- Monoalkyl phosphate
- Pyrimidone
- Hydropyrimidine
- Monosaccharide
- Organic phosphoric acid derivative
- Pyrimidine
- Alkyl phosphate
- Phosphoric acid ester
- Heteroaromatic compound
- Vinylogous amide
- Tetrahydrofuran
- Secondary alcohol
- Urea
- Lactam
- 1,2-diol
- Organoheterocyclic compound
- Carboxylic acid derivative
- Carboxylic acid
- Azacycle
- Monocarboxylic acid or derivatives
- Oxacycle
- Organic oxide
- Organopnictogen compound
- Organic oxygen compound
- Alcohol
- Hydrocarbon derivative
- Organooxygen compound
- Organic nitrogen compound
- Organonitrogen compound
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | - pyrimidine ribonucleoside 5'-monophosphate (CHEBI:15842 )
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Ontology |
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Disposition | Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: |
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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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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-9512000000-a3f8062edabfeda1eaa8 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-0002-9221230000-0c722324f49458fdfb65 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-0914000000-3337770bad1b3ba8486c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a4i-1911000000-f94acf2aa5da3364c517 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a4l-5900000000-81a1aba75871162fc05b | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0axv-8917000000-d1de3bc4514e88dd288c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-056r-9701000000-13540f203bff602cb8f5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9200000000-2bf7c464e9b79ae5c6a9 | Spectrum |
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Biological Properties |
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Cellular Locations | |
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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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| Not Available |
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Abnormal Concentrations |
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Prostate Tissue | Detected and Quantified | 0.5 (0.0-1.0) umol/g tissue | Adult (>18 years old) | Both | Prostate Cancer | | details |
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Associated Disorders and Diseases |
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Disease References | Prostate cancer |
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- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | DB02957 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB031073 |
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KNApSAcK ID | C00007583 |
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Chemspider ID | 141140 |
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KEGG Compound ID | C01103 |
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BioCyc ID | OROTIDINE-5-PHOSPHATE |
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BiGG ID | 36813 |
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Wikipedia Link | Orotidine 5'-monophosphate |
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METLIN ID | 5228 |
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PubChem Compound | 160617 |
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PDB ID | Not Available |
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ChEBI ID | 15842 |
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Food Biomarker Ontology | Not Available |
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VMH ID | OROT5P |
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MarkerDB ID | |
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References |
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Synthesis Reference | Ueda, Tohru; Yamamoto, Miyako; Yamane, Akira; Imazawa, Masaoki; Inoue, Hideo. Nucleosides and nucleotides. XXIII. Conversion of uridine nucleotides to the 6-cyano derivatives: synthesis of orotidylic acid. Journal of Carbohydrates, Nucleosides, Nucleotides (1978), 5(3), 261-71. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Traut TW: Uridine-5'-phosphate synthase: evidence for substrate cycling involving this bifunctional protein. Arch Biochem Biophys. 1989 Jan;268(1):108-15. [PubMed:2912371 ]
- Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
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