Phosphoenolpyruvic acid (YMDB00276)

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Identification

YMDB ID

YMDB00276

Name

Phosphoenolpyruvic acid

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

Phosphoenolpyruvic acid, also known as PEP or 2-phosphonooxyprop-2-enoate, belongs to the class of organic compounds known as phosphate esters. These are organic compounds containing phosphoric acid ester functional group, with the general structure R1P(=O)(R2)OR3. R1,R2 = O,N, or halogen atom; R3 = organyl group. Phosphoenolpyruvic acid is an extremely strong acidic compound (based on its pKa). Phosphoenolpyruvic acid exists in all living species, ranging from bacteria to humans.

Structure

MOL SDF PDB SMILES InChI

Synonyms

2-(phosphonooxy)-2-propenoate
2-(phosphonooxy)acrylate
2-hydroxy-2-propenoate (dihydrogen phosphate) (ester)
2-hydroxy-2-propenoate phosphate (ester)
2-hydroxy-Acrylic acid dihydrogen phosphate
2-phosphonooxyprop-2-enoate
2-phosphonooxyprop-2-enoic acid
O-phosphono-enol-pyruvate
P-enol-pyruvate
PEP
pep, phosphoenolpyruvic acid
Phosphoenolpyruvate
phosphoenolpyruvate(1-)
Phosphoenolpyruvic acid
2-(Phosphonooxy)-2-propenoic acid
2-PHOSPHOENOLPYRUVIC ACID
2-PHOSPHOENOLPYRUVate
PEP (phosphate)

CAS number

138-08-9

Weight

Average: 168.042
Monoisotopic: 167.982374404

InChI Key

DTBNBXWJWCWCIK-UHFFFAOYSA-N

InChI

InChI=1S/C3H5O6P/c1-2(3(4)5)9-10(6,7)8/h1H2,(H,4,5)(H2,6,7,8)

IUPAC Name

2-(phosphonooxy)prop-2-enoic acid

Traditional IUPAC Name

phosphoenolpyruvic acid

Chemical Formula

C₃H₅O₆P

SMILES

[H]OC(=O)C(OP(=O)(O[H])O[H])=C([H])[H]

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phosphate esters. These are organic compounds containing phosphoric acid ester functional group, with the general structure R1P(=O)(R2)OR3. R1,R2 = O,N, or halogen atom; R3 = organyl group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Phosphate esters

Alternative Parents

Substituents

Phosphoric acid ester
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:44897 )
carboxyalkyl phosphate (CHEBI:44897 )

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	13.2 g/L	ALOGPS
logP	-1.2	ALOGPS
logP	-0.64	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	0.76	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	104.06 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	30.13 m³·mol⁻¹	ChemAxon
Polarizability	11.57 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Cytoplasm
Mitochondrion

Organoleptic Properties

Not Available

SMPDB Pathways

Ethanol fermentation	PW002448
Glycolysis I	PW002386
Pyruvate metabolism	PW002447

KEGG Pathways

Citrate cycle (TCA cycle)	ec00020
Glycolysis / Gluconeogenesis	ec00010
Methane metabolism	ec00680
Phenylalanine, tyrosine and tryptophan biosynthesis	ec00400
Pyruvate metabolism	ec00620

SMPDB Reactions

2-phospho-D-glyceric acid ↔ Phosphoenolpyruvic acid + water

Adenosine triphosphate + Pyruvic acid ↔ ADP + Phosphoenolpyruvic acid

Adenosine triphosphate + Oxalacetic acid ↔ ADP + Phosphoenolpyruvic acid

KEGG Reactions

Concentrations

Intracellular Concentrations

Intracellular Concentration	Substrate	Growth Conditions	Strain	Citation
15 ± 15 µM	Synthetic medium with 2% glucose	aerobic;growing cells	Baker's yeast	PMID: 6229402
15 ± 15 µM	Synthetic medium with 2% galactose	aerobic;resting cells	Baker's yeast	PMID: 6229402
Conversion Details Here

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0292-0962000000-44d3914b4e07e5c50e3f	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0292-0962000000-44d3914b4e07e5c50e3f	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9200000000-ae9d81fc88a98f678268	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9410000000-072478606f0ab6809902	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udr-1900000000-9a4f5554af9a717d99c7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000x-9200000000-6cdc15f3daa25fc41655	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9100000000-39e22409d6d924a774f1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00xu-0912000000-ad1823470675975d5ff0	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-1f5b761ce5fa374b0f8e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-d279f0ca2accb130181f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0920000000-f084dccf78e11c8760d7	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00lr-0911000000-7fa833698210746c838f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-62e28301f20b08971b78	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-25f970898112f7b89898	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0930000000-58691b23d317c2418c33	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00p0-0493110000-9d61bb13ab5261fdf9fd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-9100000000-db409b3cfa9ebabbcb58	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4j-5090000000-1ee56bc4866301d4bf2e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0090000000-bce08b01d44391bfecad	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-016r-7900000000-ffd3b8dcd65aaea26ac3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-9000000000-ceae3587b1e7d8b3da27	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-9000000000-701a17330cd18255d625	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-9000000000-a4178ce4951e2c3dba7b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-9000000000-9d0421620a7aaa9ef33f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0k9i-1900000000-fb12ade375a7ac97f150	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0f76-8900000000-7f57e6a8e72e5992cd88	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-000j-9300000000-c02bca019150d572b3bc	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-05bf-9200000000-73fa5ca52ecc17bac380	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0079-9300000000-231346190165f44f28dc	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

References

References:

UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Thevelein, J. M., Hohmann, S. (1995). "Trehalose synthase: guard to the gate of glycolysis in yeast?" Trends Biochem Sci 20:3-10.7878741
Schwartz, J. M., Kanehisa, M. (2006). "Quantitative elementary mode analysis of metabolic pathways: the example of yeast glycolysis." BMC Bioinformatics 7:186.16584566
Braus, G. H. (1991). "Aromatic amino acid biosynthesis in the yeast Saccharomyces cerevisiae: a model system for the regulation of a eukaryotic biosynthetic pathway." Microbiol Rev 55:349-370.1943992
Larimer, F. W., Morse, C. C., Beck, A. K., Cole, K. W., Gaertner, F. H. (1983). "Isolation of the ARO1 cluster gene of Saccharomyces cerevisiae." Mol Cell Biol 3:1609-1614.6355828
Burke, R. L., Tekamp-Olson, P., Najarian, R. (1983). "The isolation, characterization, and sequence of the pyruvate kinase gene of Saccharomyces cerevisiae." J Biol Chem 258:2193-2201.6185493
Teshiba, S., Furter, R., Niederberger, P., Braus, G., Paravicini, G., Hutter, R. (1986). "Cloning of the ARO3 gene of Saccharomyces cerevisiae and its regulation." Mol Gen Genet 205:353-357.2880280
Lagunas, R., Gancedo, C. (1983). "Role of phosphate in the regulation of the Pasteur effect in Saccharomyces cerevisiae." Eur J Biochem 137:479-483.6229402

Synthesis Reference:

Simon, Ethan S.; Grabowski, Sven; Whitesides, George M. Preparation of phosphoenolpyruvate from D-(-)-3-phosphoglyceric acid for use in regeneration of ATP. Journal of the American Chemical Society (1989), 111(24), 8920-1.

External Links:

Resource	Link
CHEBI ID	44897
HMDB ID	HMDB00263
Pubchem Compound ID	1005
Kegg ID	C00074
ChemSpider ID	980
FOODB ID	FDB031112
Wikipedia	Phosphoenolpyruvic_acid
BioCyc ID	PHOSPHO-ENOL-PYRUVATE

Enzymes

Protein Details

1. Pentafunctional AROM polypeptide

General function:: Involved in 3-dehydroquinate dehydratase activity
Specific function:: The AROM polypeptide catalyzes 5 consecutive enzymatic reactions in prechorismate polyaromatic amino acid biosynthesis
Gene Name:: ARO1
Uniprot ID:: P08566
Molecular weight:: 174754.0

Reactions

3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate → 3-dehydroquinate + phosphate.
3-dehydroquinate → 3-dehydroshikimate + H(2)O.
Shikimate + NADP(+) → 3-dehydroshikimate + NADPH.
ATP + shikimate → ADP + shikimate 3-phosphate.
Phosphoenolpyruvate + 3-phosphoshikimate → phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate.

Protein Details

2. Phospho-2-dehydro-3-deoxyheptonate aldolase, tyrosine-inhibited

General function:: Involved in catalytic activity
Specific function:: Stereospecific condensation of phosphoenolpyruvate (PEP) and D-erythrose-4-phosphate (E4P) giving rise to 3-deoxy-D- arabino-heptulosonate-7-phosphate (DAHP)
Gene Name:: ARO4
Uniprot ID:: P32449
Molecular weight:: 39748.80078

Reactions

Phosphoenolpyruvate + D-erythrose 4-phosphate + H(2)O → 3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate + phosphate.

Protein Details

3. Phospho-2-dehydro-3-deoxyheptonate aldolase, phenylalanine-inhibited

General function:: Involved in catalytic activity
Specific function:: Stereospecific condensation of phosphoenolpyruvate (PEP) and D-erythrose-4-phosphate (E4P) giving rise to 3-deoxy-D- arabino-heptulosonate-7-phosphate (DAHP)
Gene Name:: ARO3
Uniprot ID:: P14843
Molecular weight:: 41069.5

Reactions

Phosphoenolpyruvate + D-erythrose 4-phosphate + H(2)O → 3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate + phosphate.

Protein Details

4. Pyruvate kinase 1

General function:: Involved in magnesium ion binding
Specific function:: ATP + pyruvate = ADP + phosphoenolpyruvate
Gene Name:: PYK1
Uniprot ID:: P00549
Molecular weight:: 54544.10156

Reactions

ATP + pyruvate → ADP + phosphoenolpyruvate.

Protein Details

5. Pyruvate kinase 2

General function:: Involved in magnesium ion binding
Specific function:: May be used by cells under conditions in which the level of glycolytic flux is very low
Gene Name:: PYK2
Uniprot ID:: P52489
Molecular weight:: 55194.69922

Reactions

ATP + pyruvate → ADP + phosphoenolpyruvate.

Protein Details

6. Phosphoenolpyruvate carboxykinase [ATP]

General function:: Involved in phosphoenolpyruvate carboxykinase (ATP) activity
Specific function:: ATP + oxaloacetate = ADP + phosphoenolpyruvate + CO(2)
Gene Name:: PCK1
Uniprot ID:: P10963
Molecular weight:: 60982.69922

Reactions

ATP + oxaloacetate → ADP + phosphoenolpyruvate + CO(2).

Protein Details

7. Enolase-related protein 1/2

General function:: Involved in magnesium ion binding
Specific function:: 2-phospho-D-glycerate = phosphoenolpyruvate + H(2)O
Gene Name:: ERR1
Uniprot ID:: Q12007
Molecular weight:: 47327.10156

Reactions

2-phospho-D-glycerate → phosphoenolpyruvate + H(2)O.

Protein Details

8. Enolase-related protein 3

General function:: Involved in magnesium ion binding
Specific function:: 2-phospho-D-glycerate = phosphoenolpyruvate + H(2)O
Gene Name:: ERR3
Uniprot ID:: P42222
Molecular weight:: 47312.10156

Reactions

2-phospho-D-glycerate → phosphoenolpyruvate + H(2)O.

Protein Details

9. Enolase 1

General function:: Involved in magnesium ion binding
Specific function:: 2-phospho-D-glycerate = phosphoenolpyruvate + H(2)O
Gene Name:: ENO1
Uniprot ID:: P00924
Molecular weight:: 46815.69922

Reactions

2-phospho-D-glycerate → phosphoenolpyruvate + H(2)O.

Protein Details

10. Enolase 2

General function:: Involved in magnesium ion binding
Specific function:: 2-phospho-D-glycerate = phosphoenolpyruvate + H(2)O
Gene Name:: ENO2
Uniprot ID:: P00925
Molecular weight:: 46913.69922

Reactions

2-phospho-D-glycerate → phosphoenolpyruvate + H(2)O.

Transporters

Protein Details

1. Tricarboxylate transport protein

General function:: Involved in binding
Specific function:: Transport of citrate across inner mitochondrial membrane
Gene Name:: CTP1
Uniprot ID:: P38152
Molecular weight:: 32173.0

Structure for #<Compound:0xa8d3de04>

Enzymes

Reactions

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Transporters