Phosphoenolpyruvic acid (CED0001426)

Record Information

Version

1.0

Creation Date

2016-05-25 21:15:52 UTC

Update Date

2026-08-22 13:13:58 UTC

Accession Number

CHEM023739

Identification

Common Name

Phosphoenolpyruvic acid

Class

Small Molecule

Description

Phosphoenolpyruvic acid is an organic compound with the chemical formula C3H5O6P and an average molecular weight of 168.04 g/mol. Phosphoenolpyruvic acid belongs to the phosphate esters, a subclass of organic phosphoric acids and derivatives within the organic compounds. This compound has been identified in or released from ten recorded sources. Within the category of food, food processing, and cookware, it is associated with fermentation processes for beer, the preparation of wort, the preparation of vinegar, the preparation of wine or sparkling wine, and food preservation. In the context of electrical and electronic equipment, it is found in electrodes, antennas, and television systems. Additionally, it is present in household cleaning and consumer products, specifically in soap detergents and tobacco smoke filters. Phosphoenolpyruvic acid interacts with six recorded protein targets. These include Beta-enolase (ENO3), 2-dehydro-3-deoxyphosphooctonate aldolase (kdsA), Phospho-2-dehydro-3-deoxyheptonate aldolase (aroF), and Phosphoenolpyruvate carboxykinase, cytosolic [GTP] (PCK1), as well as two other proteins.

Contaminant Type

Not Available

Chemical 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 Mass

168.042 g/mol

Monoisotopic Mass

167.982 g/mol

CAS Registry Number

138-08-9

IUPAC Name

2-(phosphonooxy)prop-2-enoic acid

Traditional Name

phosphoenolpyruvic acid

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 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum	splash10-0292-0962000000-44d3914b4e07e5c50e3f	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-0292-0962000000-44d3914b4e07e5c50e3f	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0002-9200000000-ae9d81fc88a98f678268	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-00di-9410000000-072478606f0ab6809902	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udr-1900000000-9a4f5554af9a717d99c7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000x-9200000000-6cdc15f3daa25fc41655	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-001i-9100000000-39e22409d6d924a774f1	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00xu-0912000000-ad1823470675975d5ff0	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0900000000-1f5b761ce5fa374b0f8e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-9000000000-d279f0ca2accb130181f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0920000000-f084dccf78e11c8760d7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00lr-0911000000-7fa833698210746c838f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000i-9000000000-62e28301f20b08971b78	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0900000000-25f970898112f7b89898	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0002-0930000000-58691b23d317c2418c33	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00p0-0493110000-9d61bb13ab5261fdf9fd	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-9100000000-db409b3cfa9ebabbcb58	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4j-5090000000-1ee56bc4866301d4bf2e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0090000000-bce08b01d44391bfecad	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-016r-7900000000-ffd3b8dcd65aaea26ac3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-9000000000-ceae3587b1e7d8b3da27	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-9000000000-701a17330cd18255d625	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-9000000000-a4178ce4951e2c3dba7b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-9000000000-9d0421620a7aaa9ef33f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0k9i-1900000000-fb12ade375a7ac97f150	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0f76-8900000000-7f57e6a8e72e5992cd88	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000j-9300000000-c02bca019150d572b3bc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-05bf-9200000000-73fa5ca52ecc17bac380	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0079-9300000000-231346190165f44f28dc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-9100000000-33b795aea615bc3ef7fc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-016r-7900000000-ffd3b8dcd65aaea26ac3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-9000000000-ceae3587b1e7d8b3da27	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-9000000000-701a17330cd18255d625	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-9000000000-a4178ce4951e2c3dba7b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-9000000000-9d0421620a7aaa9ef33f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-9100000000-db409b3cfa9ebabbcb58	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4j-5090000000-1ee56bc4866301d4bf2e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0090000000-bce08b01d44391bfecad	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-9100000000-33b795aea615bc3ef7fc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0900000000-5200e24d9bacedeb3612	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-9000000000-64c7b0a6d679df615962	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0k9i-1900000000-fb12ade375a7ac97f150	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0f76-8900000000-7f57e6a8e72e5992cd88	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-000j-9300000000-c02bca019150d572b3bc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-05bf-9200000000-73fa5ca52ecc17bac380	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0079-9300000000-231346190165f44f28dc	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0900000000-7efb465a1469d977ab37	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0900000000-25f970898112f7b89898	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-9000000000-54ff8e6208b30c8f879e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-9000000000-10d0f179adb0e6bdec0d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-9000000000-f253c7e0f0c1a8352903	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-004i-9000000000-8310e25f1579dbfbf6f4	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-9300000000-f4e07ab797c1ea1ae90a	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00dj-8900000000-d39d27de1a0b1d957520	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00fr-9000000000-467bad7c9b7c2405fe64	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-9400000000-c466468eb93d1e833684	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-9100000000-360e74988c0b0ff5d788	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-9000000000-a4ce2513b4bd02cf5915	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0udi-0900000000-a852762389cc0a5ced1f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00e9-9600000000-38ea6caf33601fd5034b	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-001i-9000000000-85f0aa63ef18850dc13e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-9000000000-a5e502a2627af2048a1f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-9000000000-a5e502a2627af2048a1f	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-004i-9000000000-a5e502a2627af2048a1f	Not Available	View Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, predicted)	Not Available	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Not Available

Carcinogenicity (IARC Classification)

Not Available

Minimum Risk Level

Not Available

Symptoms

Not Available

Treatment

Not Available

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
2029.0	Log mg/kg	[1100:3600]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference

Exposure Sources

Source ID	Source	Sector	Reference
10	Insecticides	Agriculture & land management	Not Available
233	Brushes	Personal care & cosmetics	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
519	Electrodes	Electrical & Electronic Equipment	Not Available
537	Television Systems	Electrical & Electronic Equipment	Not Available
544	Fermentation Processes For Beer	Food, food processing & cookware	Not Available
545	Food Preservation	Food, food processing & cookware	Not Available
548	Preparation Of Vinegar	Food, food processing & cookware	Not Available
549	Preparation Of Wine Or Sparkling Wine	Food, food processing & cookware	Not Available
550	Preparation Of Wort	Food, food processing & cookware	Not Available
563	Soap Detergents	Household cleaning & consumer products	Not Available
569	Tobacco Smoke Filters	Household cleaning & consumer products	Not Available
580	Manufacture Preparation Of Tobacco Products	Industrial manufacturing & chemical processing	Not Available
600	Herbicides And Algicides	Agriculture & land management	Not Available
601	Lawn Mowers	Agriculture & land management	Not Available
603	Nematocides	Agriculture & land management	Not Available
606	Plant Growth Regulators	Agriculture & land management	Not Available
610	Aftersun Products	Personal care & cosmetics	Not Available
611	Anti Perspirants Or Body Deoderants	Personal care & cosmetics	Not Available
614	Essential Oils Or Perfumes	Personal care & cosmetics	Not Available
632	Apparel	Textiles, leather & furnishings	Not Available

Pathways

39 pathways

Amino Sugar Metabolism

Pyruvate Metabolism

Leigh Syndrome

Pyruvate Decarboxylase E1 Component Deficiency (PDHE1 Deficiency)

Pyruvate Dehydrogenase Complex Deficiency

Sialuria or French Type Sialuria

Salla Disease/Infantile Sialic Acid Storage Disease

Glycolysis

Gluconeogenesis

Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke Disease

Tay-Sachs Disease

Glycogenosis, Type VII. Tarui Disease

View all 39 pathways

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Fructose-bisphosphate aldolase class 2	P0AB71	Escherichia coli (strain K12)	Predicted (SEA)	0.544945
Click to view 3D structure	Ribose-5-phosphate isomerase B	P9WKD7	Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)	Predicted (SEA)	0.544945
Click to view 3D structure	Inositol 1,4,5-trisphosphate-gated calcium channel ITPR3	Q8WN95	Bos taurus	Predicted (SEA)	0.856341
Click to view 3D structure	Phosphatidylinositol 3,4,5-trisphosphate 5-phosphatase 2	Q6P549	Mus musculus	Predicted (SEA)	0.467095
Click to view 3D structure	Type II inositol 1,4,5-trisphosphate 5-phosphatase	P32019	Humans	Predicted (SEA)	0.467095
Click to view 3D structure	6-phosphogluconolactonase	Q9GRG6	Trypanosoma brucei	Predicted (SEA)	0.544945
Click to view 3D structure	Diphosphomevalonate decarboxylase	P53602	Humans	Predicted (SEA)	3.65891
Click to view 3D structure	Triosephosphate isomerase	P00939	Oryctolagus cuniculus	Predicted (SEA)	0.389246
Click to view 3D structure	Inositol-trisphosphate 3-kinase A	P17105	Rattus norvegicus	Predicted (SEA)	1.01204
Click to view 3D structure	2-dehydro-3-deoxyphosphooctonate aldolase	Q9JZ55	Neisseria meningitidis serogroup B (strain MC58)	Predicted (SEA)	2.72472
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	1737.28
Click to view 3D structure	Inositol polyphosphate-5-phosphatase A	Q14642	Humans	Predicted (SEA)	0.544945
Click to view 3D structure	Metabotropic glutamate receptor 6	P35349	Rattus norvegicus	Predicted (SEA)	50.602
Click to view 3D structure	Fructose-bisphosphate aldolase A	P00883	Oryctolagus cuniculus	Predicted (SEA)	0.934191
Click to view 3D structure	Inositol 1,4,5-trisphosphate-gated calcium channel ITPR3	Q14573	Humans	Predicted (SEA)	1.24559
Click to view 3D structure	Type 1 InsP3 receptor isoform S2	P79248	Sus scrofa	Predicted (SEA)	1.08989
Click to view 3D structure	Metabotropic glutamate receptor 4	P31423	Rattus norvegicus	Predicted (SEA)	426.069
Click to view 3D structure	1-deoxy-D-xylulose-5-phosphate synthase	B7UJP3	Escherichia coli O127:H6 (strain E2348/69 / EPEC)	Predicted (SEA)	4.67095
Click to view 3D structure	Inositol 1,4,5-trisphosphate binding protein	Q62688	Rattus norvegicus	Predicted (SEA)	1.16774
Click to view 3D structure	Metabotropic glutamate receptor 4	Q14833	Humans	Predicted (SEA)	852.682
Click to view 3D structure	Phospho-2-dehydro-3-deoxyheptonate aldolase	C3TIE2	Escherichia coli	Predicted (SEA)	2.49118
Click to view 3D structure	Fructose-bisphosphate aldolase	P56109	Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacterpylori)	Predicted (SEA)	1.94623
Click to view 3D structure	Arabinose 5-phosphate isomerase KdsD	Q5NGP7	Francisella tularensis subsp. tularensis (strain SCHU S4 / Schu 4)	Predicted (SEA)	1.24559
Click to view 3D structure	72 kDa type IV collagenase	P08253	Humans	Predicted (SEA)	3624.66
Click to view 3D structure	Fructose-bisphosphate aldolase class II	A0A380PJR2	Yersinia pestis	Predicted (SEA)	2.02408