View source for Chemistry:Orotidine 5'-monophosphate

{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 428737673
|ImageFile=Orotidine monophosphate.svg
|ImageSize=
| IUPACName =3-[(2R,3R,4S,5R)-3,4-dihydroxy-5-&#8203;(phosphonooxymethyl)oxolan-2-yl]&#8203;-2,6-dioxo-pyrimidine-4-carboxylic acid
|OtherNames= Orotidylic acid,<br>OMP
|Section1= {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=2149-82-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = H0ARN8U4Y9
|  PubChem = 160617
|  ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 141140
|  SMILES = c1c(n(c(=O)nc1O)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O)C(=O)O
|  InChI = 1/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
|  InChIKey = KYOBSHFOBAOFBF-XVFCMESIBC
|  StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
|  StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = KYOBSHFOBAOFBF-XVFCMESISA-N

| MeSHName=Orotidine+5'-monophosphate
  }}
|Section2= {{Chembox Properties
| Formula=C<sub>10</sub>H<sub>13</sub>N<sub>2</sub>O<sub>11</sub>P
| MolarMass=368.191 g/mol
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
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|Section3= {{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt=
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'''Orotidine 5'-monophosphate''' ('''OMP'''), also known as '''orotidylic acid''',  is a [[Chemistry:Pyrimidine|pyrimidine]] [[Biology:Nucleotide|nucleotide]] which is the last intermediate in the biosynthesis of [[Chemistry:Uridine monophosphate|uridine monophosphate]]. OMP is formed from [[Chemistry:Orotic acid|orotate]] and [[Chemistry:Phosphoribosyl pyrophosphate|phosphoribosyl pyrophosphate]] by the enzyme [[Biology:Orotate phosphoribosyltransferase|orotate phosphoribosyltransferase]]

In humans, the enzyme UMP synthase converts OMP into uridine 5'- monophosphate. If UMP synthase is defective, [[Medicine:Orotic aciduria|orotic aciduria]] can result.

{{Nucleotide metabolism intermediates}}

[[Category:Nucleotides]]
[[Category:Pyrimidinediones]]


{{Unreferenced|date=2021}}
{{Sourceattribution|Orotidine 5'-monophosphate}}