Bovine Metabolome Database: Showing metabocard for Phosphoenolpyruvic acid (BMDB0000263)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (9) Show 9 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:35 UTC

Update Date

2020-05-21 16:28:28 UTC

BMDB ID

BMDB0000263

Secondary Accession Numbers

BMDB00263

Metabolite Identification

Common Name

Phosphoenolpyruvic acid

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 possibly soluble (in water) and 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

Value	Source
2-(Phosphonooxy)-2-propenoic acid	ChEBI
2-PHOSPHOENOLPYRUVIC ACID	ChEBI
PEP	ChEBI
PHOSPHOENOLPYRUVATE	ChEBI
2-(Phosphonooxy)-2-propenoate	Generator
2-PHOSPHOENOLPYRUVate	Generator
2-Hydroxy-acrylic acid dihydrogen phosphate	HMDB
2-Phosphonooxyprop-2-enoate	HMDB
2-Phosphonooxyprop-2-enoic acid	HMDB
p-enol-Pyruvate	HMDB
PEP (phosphate)	HMDB
Phosphoenolpyruvic acid	HMDB

Chemical Formula

C₃H₅O₆P

Average Molecular Weight

168.042

Monoisotopic Molecular Weight

167.982374404

IUPAC Name

2-(phosphonooxy)prop-2-enoic acid

Traditional Name

phosphoenolpyruvic acid

CAS Registry Number

138-08-9

SMILES

OC(=O)C(=C)OP(O)(O)=O

InChI Identifier

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

InChI Key

DTBNBXWJWCWCIK-UHFFFAOYSA-N

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 )

Ontology

Status

Detected but not Quantified

Origin

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Mitochondria

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0292-0962000000-44d3914b4e07e5c50e3f	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0292-0962000000-44d3914b4e07e5c50e3f	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9200000000-ae9d81fc88a98f678268	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9410000000-072478606f0ab6809902	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udr-1900000000-9a4f5554af9a717d99c7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000x-9200000000-6cdc15f3daa25fc41655	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9100000000-39e22409d6d924a774f1	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00xu-0912000000-ad1823470675975d5ff0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-1f5b761ce5fa374b0f8e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-d279f0ca2accb130181f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0920000000-f084dccf78e11c8760d7	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00lr-0911000000-7fa833698210746c838f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-62e28301f20b08971b78	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-25f970898112f7b89898	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0930000000-58691b23d317c2418c33	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00p0-0493110000-9d61bb13ab5261fdf9fd	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-9100000000-db409b3cfa9ebabbcb58	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4j-5090000000-1ee56bc4866301d4bf2e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0090000000-bce08b01d44391bfecad	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-016r-7900000000-ffd3b8dcd65aaea26ac3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-9000000000-ceae3587b1e7d8b3da27	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-9000000000-701a17330cd18255d625	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-9000000000-a4178ce4951e2c3dba7b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-9000000000-9d0421620a7aaa9ef33f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0k9i-1900000000-fb12ade375a7ac97f150	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0f76-8900000000-7f57e6a8e72e5992cd88	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-000j-9300000000-c02bca019150d572b3bc	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-05bf-9200000000-73fa5ca52ecc17bac380	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0079-9300000000-231346190165f44f28dc	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Mitochondria

Biospecimen Locations

Liver
Milk
Placenta
Prostate Tissue

Pathways

Name	SMPDB/Pathwhiz	KEGG
Amino Sugar Metabolism		Not Available
Glycolysis		Not Available
Gluconeogenesis		Not Available
Pyruvate Metabolism		Not Available
Warburg Effect		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 23438684	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000263

DrugBank ID

DB01819

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

PHOSPHO-ENOL-PYRUVATE

BiGG ID

Not Available

Wikipedia Link

Phosphoenolpyruvic_acid

METLIN ID

Not Available

PubChem Compound

1005

PDB ID

Not Available

ChEBI ID

44897

References

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.

Material Safety Data Sheet (MSDS)

Not Available

General References

Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]

Enzymes

Enzyme Details

1. M1-type pyruvate kinase

General function:: Carbohydrate transport and metabolism
Specific function:: Not Available
Gene Name:: PKM
Uniprot ID:: B3IVN4
Molecular weight:: 16527.0

Enzyme Details

2. Beta-enolase

General function:: Carbohydrate transport and metabolism
Specific function:: Appears to have a function in striated muscle development and regeneration.
Gene Name:: ENO3
Uniprot ID:: Q3ZC09
Molecular weight:: 47096.0

Enzyme Details

3. Pyruvate kinase

General function:: Carbohydrate transport and metabolism
Specific function:: Not Available
Gene Name:: PKM2
Uniprot ID:: Q3ZC87
Molecular weight:: 61428.0

Enzyme Details

4. Alpha-enolase

General function:: Carbohydrate transport and metabolism
Specific function:: Glycolytic enzyme the catalyzes the conversion of 2-phosphoglycerate to phosphoenolpyruvate (By similarity). In addition to glycolysis, involved in various processes such as growth control, hypoxia tolerance and allergic responses (PubMed:7499243). May also function in the intravascular and pericellular fibrinolytic system due to its ability to serve as a receptor and activator of plasminogen on the cell surface of several cell-types such as leukocytes and neurons (By similarity). Stimulates immunoglobulin production (By similarity).
Gene Name:: ENO1
Uniprot ID:: Q9XSJ4
Molecular weight:: 47326.0

Reactions

2-Phospho-D-glyceric acid → Phosphoenolpyruvic acid + Water	details

Enzyme Details

5. Pyruvate kinase

General function:: Carbohydrate transport and metabolism
Specific function:: Not Available
Gene Name:: PKLR
Uniprot ID:: Q1JPG7
Molecular weight:: 56870.0

Enzyme Details

6. ENO2 protein

General function:: Carbohydrate transport and metabolism
Specific function:: Not Available
Gene Name:: ENO2
Uniprot ID:: A6QR19
Molecular weight:: 47269.0

Enzyme Details

7. Pyruvate kinase

General function:: Carbohydrate transport and metabolism
Specific function:: Not Available
Gene Name:: PKM
Uniprot ID:: A5D984
Molecular weight:: 57949.0

Reactions

Adenosine triphosphate + Pyruvic acid → ADP + Phosphoenolpyruvic acid	details

Enzyme Details

8. Phosphoenolpyruvate carboxykinase, cytosolic [GTP]

General function:: Energy production and conversion
Specific function:: Regulates cataplerosis and anaplerosis, the processes that control the levels of metabolic intermediates in the citric acid cycle. At low glucose levels, it catalyzes the cataplerotic conversion of oxaloacetate (OAA) to phosphoenolpyruvate (PEP), the rate-limiting step in the metabolic pathway that produces glucose from lactate and other precursors derived from the citric acid cycle. At high glucose levels, it catalyzes the anaplerotic conversion of phosphoenolpyruvate to oxaloacetate.
Gene Name:: PCK1
Uniprot ID:: Q8HYZ4
Molecular weight:: 69353.0

Reactions

Guanosine triphosphate + Oxalacetic acid → Guanosine diphosphate + Phosphoenolpyruvic acid + Carbon dioxide	details

Enzyme Details

9. N-acetylneuraminate synthase

General function:: Not Available
Specific function:: Not Available
Gene Name:: NANS
Uniprot ID:: Q1RMX7
Molecular weight:: 40217.0

Reactions

N-Acetyl-D-mannosamine + Phosphoenolpyruvic acid + Water → N-Acetylneuraminic acid + Hydrogen phosphate	details

Showing metabocard for Phosphoenolpyruvic acid (BMDB0000263)

Structure for BMDB0000263 (Phosphoenolpyruvic acid)

Enzymes

Reactions

Reactions

Reactions

Reactions