Orotidine 5'-monophosphate: Difference between revisions

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	{{chembox		{{chembox
			\| Verifiedfields = changed
			\| Watchedfields = changed
			\| verifiedrevid = 428737673
	\|ImageFile=Orotidine monophosphate.svg		\|ImageFile=Orotidine monophosphate.svg
	\|ImageSize=		\|ImageSize=
	\| IUPACName =3-~~~~-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=
			\|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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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	2149-82-8
3D model (JSmol)	Interactive image
ChemSpider	141140
MeSH	Orotidine+5'-monophosphate
PubChem CID	160617
UNII	H0ARN8U4Y9
CompTox Dashboard (EPA)	DTXSID40944090
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

PubChem. "Orotidine-5'-monophosphate". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-01-26.
^ "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:	Ribose 5-phosphate (R5P) Phosphoribosyl pyrophosphate (PRPP) Phosphoribosylamine (PRA) Glycineamide ribonucleotide (GAR) Phosphoribosyl-N-formylglycineamide (FGAR) 5′-Phosphoribosylformylglycinamidine (FGAM) 5-Aminoimidazole ribotide (AIR) 5′-Phosphoribosyl-4-carboxy-5-aminoimidazole (CAIR) Phosphoribosylaminoimidazolesuccinocarboxamide (SAICAR) AICA ribonucleotide (AICAR) 5-Formamidoimidazole-4-carboxamide ribotide (FAICAR)
IMP→AMP:	Adenylosuccinate
IMP→GMP:	Xanthosine monophosphate

catabolism

pyrimidine
metabolism

anabolism

catabolism

uracil:	β-Alanine Dihydrouracil 3-Ureidopropionic acid
thymine:	3-Aminoisobutyric acid Dihydrothymine β-Ureidoisobutyric acid

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