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Revision as of 12:53, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,055 edits Saving copy of the {{chembox}} taken from revid 456781584 of page Phosphoenolpyruvic_acid for the Chem/Drugbox validation project (updated: '').		Latest revision as of 06:26, 2 January 2025 edit Arthurfragoso (talk | contribs)Extended confirmed users, Template editors4,591 edits Fixes image in dark mode
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			{{Short description|Chemical compound}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
	{{chembox		{{chembox
			| Watchedfields = changed
	| verifiedrevid = 444051320		| verifiedrevid = 464205172
	| ImageFile_Ref = {{chemboximage|correct|??}}		| ImageFile_Ref = {{chemboximage|correct|??}}
	| ImageFile=Phosphoenolpyruvic acid.svg		| ImageFile=Phosphoenolpyruvic acid.svg
	|ImageSize=		| ImageSize=
			| ImageClass = skin-invert
	|IUPACName=2-(phosphonooxy)acrylic acid
			| ImageFile2 = Phosphoenolpyruvic-acid-from-xtal-3D-bs-17.png
⚫	|OtherNames=Phosphoenolpyruvic acid, PEP
			| PIN=2-(Phosphonooxy)prop-2-enoic acid
⚫	|Section1= {{Chembox Identifiers
		⚫	| OtherNames=Phosphoenolpyruvic acid, PEP
⚫	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
		⚫	|Section1={{Chembox Identifiers
			| IUPHAR_ligand = 4692
		⚫	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)		| StdInChI = 1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
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	| CASNo_Ref = {{cascite|correct|CAS}}		| CASNo_Ref = {{cascite|correct|CAS}}
	| CASNo=138-08-9		| CASNo=138-08-9
			| UNII_Ref = {{fdacite|correct|FDA}}
⚫	| PubChem=1005
			| UNII = 545YL308OW
⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
		⚫	| PubChem=1005
		⚫	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 980		| ChemSpiderID = 980
	| DrugBank_Ref = {{drugbankcite|correct|drugbank}}		| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
	| DrugBank = DB01819		| DrugBank = DB01819
	| ChEBI_Ref = {{ebicite|correct|EBI}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 44897		| ChEBI = 44897
			| KEGG_Ref = {{keggcite|correct|kegg}}
			| KEGG = C00074
	| SMILES = O=C(O)C(OP(=O)(O)O)=C		| SMILES = O=C(O)C(OP(=O)(O)O)=C
	}}		}}
	|Section2= {{Chembox Properties		|Section2={{Chembox Properties
	| C=3|H=5|O=6|P=1		| C=3 | H=5 | O=6 | P=1
	| MolarMass=168.042		| MolarMass=168.042
	| Appearance=		| Appearance=
	| Density=		| Density=
	| MeltingPt=		| MeltingPt=
	| BoilingPt=		| BoilingPt=
	| Solubility=		| Solubility=
	}}		}}
	|Section3= {{Chembox Hazards		|Section3={{Chembox Hazards
	| MainHazards=		| MainHazards=
	| FlashPt=		| FlashPt=
			| AutoignitionPt =
	| Autoignition=
	}}		}}
	}}		}}
			'''Phosphoenolpyruvate''' ('''2-phosphoenolpyruvate''', '''PEP''') is the ] derived from the ] of ] and ]. It exists as an ]. PEP is an important intermediate in ]. It has the ] bond found (−61.9 kJ/mol) in organisms, and is involved in ] and ]. In plants, it is also involved in the biosynthesis of various ] compounds, and in ]; in bacteria, it is also used as the source of energy for the ].<ref>{{cite book |last=Berg |first=Jeremy M. |author2=Tymoczko, Stryer |title=Biochemistry |year=2002 |edition=5th |publisher=] |location=New York |isbn=0-7167-3051-0 |url=https://archive.org/details/biochemistrychap00jere |url-access=registration }}</ref><ref>Nelson, D. L.; Cox, M. M. "Lehninger, Principles of Biochemistry" 3rd Ed. Worth Publishing: New York, 2000. {{ISBN|1-57259-153-6}}.</ref>
			==In glycolysis==
			PEP is formed by the action of the ] ] on ]. Metabolism of PEP to ] by ] (PK) generates ] (ATP) via ]. ATP is one of the major currencies of chemical energy within ]s.
			{| style="background: white; text-align:center;"
			|-
			| style="background:lightgreen" | ]
			| colspan="2" style="background:pink; width:75px" | ]
			| style="background:lightgreen" | '''phosphoenolpyruvate'''
			| colspan="2" style="background:pink; width:75px" | ]
			| style="background:lightgreen" | ]
			|-
			| rowspan="5" | ]
			| colspan="2" style="width:75px" | &nbsp;
			| rowspan="5" | ]
			| colspan="2" style="width:75px" | &nbsp;
			| rowspan="5" | ]
			|-
			|
			| H<sub>2</sub>O
			| ]
			| ]
			|-
			| colspan="2" style="width:75px" | ]
			| colspan="2" style="width:75px" |]
			|-
			|
			| H<sub>2</sub>O
			|
			|
			|-
			| colspan="2" style="width:75px" | &nbsp;
			| colspan="2" style="width:75px" | &nbsp;
			|}
			{{KEGG compound|C00631}} {{KEGG enzyme|4.2.1.11}} {{KEGG compound|C00074}} {{KEGG enzyme|2.7.1.40}} {{KEGG compound|C00022}}
			==In gluconeogenesis==
			PEP is formed from the ] of ] and ] of one ] molecule. This reaction is ] by the enzyme ] (PEPCK). This reaction is a ] in gluconeogenesis:<ref>{{cite web |url=http://www.ebi.ac.uk/interpro/IEntry?ac=IPR008209 |title=InterPro: IPR008209 Phosphoenolpyruvate carboxykinase, GTP-utilising |access-date=2007-08-17 }}</ref>
			:GTP + oxaloacetate → GDP + phosphoenolpyruvate + CO<sub>2</sub>
			== Interactive pathway map ==
			{{GlycolysisGluconeogenesis_WP534|highlight=Phosphoenolpyruvic_acid}}
			== In plants ==
			PEP may be used for the synthesis of ] through the ].<ref>{{cite web |url=http://www.biocarta.com/pathfiles/chorismatePathway.asp |title=BioCarta - Charting Pathways of Life |access-date=2007-08-17 }}</ref> Chorismate may then be metabolized into the aromatic ]s (], ] and ]) and other aromatic compounds. The first step is when Phosphoenolpyruvate and ] react to form ] (DAHP), in a reaction catalyzed by the enzyme ].
			:]{{clear-left}}
			In addition, in ], PEP serves as an important ] in ]. The chemical equation, as catalyzed by ] (PEP carboxylase), is:
			:PEP + {{chem2|HCO3(−)}} → oxaloacetate
			==References==
			<references />
			{{glycolysis}}
			]
			]
			]
			]