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Orotidine 5'-monophosphate: Difference between revisions

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Revision as of 21:13, 20 April 2011 editKupirijo (talk | contribs)Extended confirmed users9,146 edits |OtherNames= Orotidylic acid,<br>OMP← Previous edit Latest revision as of 03:44, 6 May 2023 edit undoLegionMammal978 (talk | contribs)Extended confirmed users7,895 edits add semisystematic name 
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{{chembox {{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 428737673
|ImageFile=Orotidine monophosphate.svg |ImageFile=Orotidine monophosphate.svg
|ImageSize= |ImageSize=
| IUPACName =3-&#8203;-2,6-dioxo-pyrimidine-4-carboxylic acid | IUPACName = 2,6-Dioxo-3-(5-''O''-phosphono-β-<small>D</small>-ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
| SystematicName = 3-{(2''R'',3''R'',4''S'',5''R'')-3,4-Dihydroxy-6-oxolan-2-yl}-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
|OtherNames= Orotidylic acid,<br>OMP |OtherNames= Orotidylic acid,<br>OMP
|Section1= {{Chembox Identifiers |Section1= {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=2149-82-8 | CASNo=2149-82-8
⚫ | PubChem=968
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | SMILES= C1=C(N(C(=O)NC1=O)C2C(C(C(O2)COP(=O)(O)O)O)O)C(=O)O
| UNII = H0ARN8U4Y9
⚫ | MeSHName=Orotidine+5'-monophosphate
⚫ | PubChem = 160617
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 141140
⚫ | SMILES = c1c(n(c(=O)nc1O)2(((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 |Section2= {{Chembox Properties
| Formula=C<sub>10</sub>H<sub>13</sub>N<sub>2</sub>O<sub>11</sub>P | Formula=C<sub>10</sub>H<sub>13</sub>N<sub>2</sub>O<sub>11</sub>P
| MolarMass=368.191 g/mol | MolarMass=368.191 g/mol
| Appearance= | Appearance=
| Density= | Density=
| MeltingPt= | MeltingPt=
| BoilingPt= | BoilingPt=
| Solubility= | Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3= {{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt=
| Autoignition=
}} }}
}} }}
'''Orotidine 5'-monophosphate''' (OMP), also known as '''orotidylic acid,''' is a ] ] which is the last intermediate in the biosynthesis of ]. OMP is formed from ] and ] by the enzyme ] '''Orotidine 5'-monophosphate''' ('''OMP'''), also known as '''orotidylic acid''', is a ] ]<ref>{{Cite web |last=PubChem |title=Orotidine-5'-monophosphate |url=https://pubchem.ncbi.nlm.nih.gov/compound/160617 |access-date=2023-01-26 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref> which is the last intermediate in the biosynthesis of ].<ref name=":0">{{Cite web |title=UMPS uridine monophosphate synthetase - Gene - NCBI |url=https://www.ncbi.nlm.nih.gov/gene?Db=gene&Cmd=ShowDetailView&TermToSearch=7372 |access-date=2023-01-26 |website=www.ncbi.nlm.nih.gov}}</ref> OMP is formed from ] and ] by the enzyme ].


In humans, the enzyme ] converts OMP into ]. If UMP synthase is defective, ] can result. In humans, the enzyme ] converts OMP into ].<ref name=":0" /> If UMP synthase is defective, ] can result.<ref name=":0" />

==References==
{{reflist}}


{{Nucleotide metabolism intermediates}} {{Nucleotide metabolism intermediates}}
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] ]
] ]



{{biochem-stub}} {{biochem-stub}}

]
]

Latest revision as of 03:44, 6 May 2023

Orotidine 5'-monophosphate
Names
IUPAC name 2,6-Dioxo-3-(5-O-phosphono-β-D-ribofuranosyl)-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
Systematic IUPAC name 3-{(2R,3R,4S,5R)-3,4-Dihydroxy-6-oxolan-2-yl}-2,6-dioxo-1,2,3,6-tetrahydropyrimidine-4-carboxylic acid
Other names Orotidylic acid,
OMP
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
MeSH Orotidine+5'-monophosphate
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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/s1Key: KYOBSHFOBAOFBF-XVFCMESISA-N
  • 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/s1Key: KYOBSHFOBAOFBF-XVFCMESIBC
SMILES
  • c1c(n(c(=O)nc1O)2(((O2)COP(=O)(O)O)O)O)C(=O)O
Properties
Chemical formula C10H13N2O11P
Molar mass 368.191 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Orotidine 5'-monophosphate (OMP), also known as orotidylic acid, is a pyrimidine nucleotide which is the last intermediate in the biosynthesis of uridine monophosphate. OMP is formed from orotate and phosphoribosyl pyrophosphate by the enzyme orotate phosphoribosyltransferase.

In humans, the enzyme UMP synthase converts OMP into uridine 5'- monophosphate. If UMP synthase is defective, orotic aciduria can result.

References

  1. PubChem. "Orotidine-5'-monophosphate". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-01-26.
  2. ^ "UMPS uridine monophosphate synthetase [Homo sapiens (human)] - Gene - NCBI". www.ncbi.nlm.nih.gov. Retrieved 2023-01-26.
Nucleotide metabolic intermediates
purine
metabolism
anabolism
R5P→IMP:
IMP→AMP:Adenylosuccinate
IMP→GMP:Xanthosine monophosphate
catabolism
pyrimidine
metabolism
anabolism
catabolism
uracil:
thymine:
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