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Uridine monophosphate information


Uridine monophosphate
Skeletal formula of UMP
Ball-and-stick model of the UMP molecule as an anion
Names
IUPAC name
[(2R,3S,4R,5R)-5-(2,4-Dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
Other names
Uridylic acid; Uridine 5'-monophosphate; 5'-Uridylic acid; Uridine 5'-phosphate; Uridine phosphate; 5'-UMP; Uridine 5'-phosphoric acid
Identifiers
CAS Number
  • 58-97-9 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 5808 ☒N
ECHA InfoCard 100.000.371 Edit this at Wikidata
IUPHAR/BPS
  • 5125
MeSH Uridine+monophosphate
PubChem CID
  • 6030
UNII
  • E2OU15WN0N checkY
CompTox Dashboard (EPA)
  • DTXSID40861596 DTXSID20883211, DTXSID40861596 Edit this at Wikidata
InChI
  • InChI=1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1 ☒N
    Key: DJJCXFVJDGTHFX-XVFCMESISA-N ☒N
  • InChI=1/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1
    Key: DJJCXFVJDGTHFX-XVFCMESIBD
SMILES
  • c1cn(c(=O)[nH]c1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O
Properties
Chemical formula
C9H13N2O9P
Molar mass 324.182 g·mol−1
Melting point 202 °C (396 °F; 475 K) (decomposes)[1]
Solubility in water
good, also in methanol [1]
Acidity (pKa) 1.0, 6.4, 9.5
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Uridine monophosphate (UMP), also known as 5′-uridylic acid (conjugate base uridylate), is a nucleotide that is used as a monomer in RNA. It is an ester of phosphoric acid with the nucleoside uridine. UMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase uracil; hence, it is a ribonucleotide monophosphate. As a substituent or radical its name takes the form of the prefix uridylyl-. The deoxy form is abbreviated dUMP. Covalent attachment of UMP (e.g., to a protein such as adenylyltransferase) is called uridylylation (or sometimes uridylation).[2]

  1. ^ a b Lide M, Lide DR (1998). CRC Handbook of Chemistry and Physics (87 ed.). CRC Press. pp. 3–56. ISBN 978-0-8493-0594-8.
  2. ^ Voet D, Voet JG, Pratt CW (2008). Fundamentals of Biochemistry (3rd ed.). John Wiley & Sons.

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Uridine monophosphate

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Uridine monophosphate (UMP), also known as 5′-uridylic acid (conjugate base uridylate), is a nucleotide that is used as a monomer in RNA. It is an ester...

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Uridine monophosphate synthase

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The enzyme Uridine monophosphate synthase (EC 4.1.1.23, UMPS) (orotate phosphoribosyl transferase and orotidine-5'-decarboxylase) catalyses the formation...

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Uridine

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they would be represented as dA, dC and dG. Uridine is widely produced in nature as uridine monophosphate (uridylate) by de novo synthesis by the decarboxylation...

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Deoxyuridine monophosphate

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Deoxyuridine monophosphate (dUMP) is the deoxygenated form of uridine monophosphate (UMP), and is the precursor to deoxythymidine monophosphate (dTMP), a...

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Nucleic acid metabolism

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the end of the process. After synthesizing uridine-monophosphate, it can react with 2 ATP to form uridine-triphosphate or UTP. UTP can be converted to...

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Monophosphate

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Nucleoside monophosphate Uridine monophosphate Cytidine monophosphate Thymidine monophosphate Guanosine monophosphate Thiamine monophosphate Deoxyadenosine...

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Cytidine monophosphate

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generated by amination of uridine triphosphate, the main source of CMP is from RNA being decomposed by RNAse. Deoxycytidine monophosphate Nucleoside Oligonucleotide...

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Cyclic nucleotide

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also involved in eukaryotic cellular messaging. The role of cyclic uridine monophosphate (cUMP) is even less well known. Discovery of cyclic nucleotides...

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Nucleotide

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decarboxylated by orotidine-5'-phosphate decarboxylase to form uridine monophosphate (UMP). PRPP transferase catalyzes both the ribosylation and decarboxylation...

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Nucleotide salvage

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nucleoside uridine. Uridine kinase (aka uridine–cytidine kinase) can then phosphorylate the 5’-carbon of this nucleoside into uridine monophosphate (UMP)....

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Adenosine monophosphate

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Adenosine monophosphate (AMP), also known as 5'-adenylic acid, is a nucleotide. AMP consists of a phosphate group, the sugar ribose, and the nucleobase...

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Uracil

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ribose sugar to form the ribonucleoside uridine. When a phosphate attaches to uridine, uridine 5′-monophosphate is produced. Uracil undergoes amide-imidic...

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Human enhancement

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Huperzine A, Phosphatidylserine, Bacopa monnieri, Acetyl-L-carnitine, Uridine monophosphate, L-theanine, Rhodiola rosea, and Pycnogenol which are all forms...

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Orotic aciduria

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sequencing of the UMPS gene. Treatment is administration of uridine monophosphate (UMP) or uridine triacetate (which is converted to UMP). These medications...

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UCK2

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gene catalyzes the phosphorylation of uridine and cytidine to uridine monophosphate (UMP) and cytidine monophosphate (CMP), respectively. This is the first...

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Biosynthesis

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are thymine, cytosine and uracil (which is only found in RNA). Uridine monophosphate biosynthesis involves an enzyme that is located in the mitochondrial...

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UMP

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Uniformly most powerful test, in statistical hypothesis testing Uridine monophosphate, a nucleotide Utility maximization problem Ulba Metallurgical Plant...

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Leflunomide

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dehydrogenase (DHODH), which plays a key role in the de novo synthesis of uridine monophosphate (rUMP), which is required for the synthesis of DNA and RNA. Hence...

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Souvenaid

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docosahexaenoic acid, eicosapentaenoic acid, phospholipids, choline, uridine monophosphate, vitamin E (alpha-tocopherol equivalents), selenium, vitamin B12...

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Ribonucleotide

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utilized in both cell regulation and cell signaling as seen in adenosine-monophosphate (AMP). Furthermore, ribonucleotides can be converted to adenosine triphosphate...

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Guanosine monophosphate

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Guanosine monophosphate (GMP), also known as 5′-guanidylic acid or guanylic acid (conjugate base guanylate), is a nucleotide that is used as a monomer...

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Galactosamine

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UDP-galactosamine accumulation within cells, and uridine triphosphate (UTP), UDP, and uridine monophosphate (UMP) decrease. The depletion of high-energy molecules...

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Primary transcript

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ribonucleoside monophosphate residues (adenosine monophosphate (AMP), cytidine monophosphate (CMP), guanosine monophosphate (GMP), and uridine monophosphate (UMP))...

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Orotate phosphoribosyltransferase

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mammals, this bifunctional enzyme UMPS converts orotic acid into uridine monophosphate (UMP). Orotate phosphoribosyltransferase is located at the N-terminal...

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Inosinic acid

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