Cannabis Compound Database: Showing Compound Card for Phosphoenolpyruvic acid (CDB005089)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (11)transporters (1) Show 23 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 19:08:13 UTC

Updated at

2020-11-18 16:39:19 UTC

CannabisDB ID

CDB005089

Secondary Accession Numbers

Not Available

Cannabis Compound 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 an extremely strong acidic compound (based on its pKa). Phosphoenolpyruvic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, Phosphoenolpyruvic acid has been detected, but not quantified in, several different foods, such as pepper (c. frutescens), grapes, mexican groundcherries, black raspberries, and wasabis. This could make phosphoenolpyruvic acid a potential biomarker for the consumption of these foods. Phosphoenolpyruvic acid is expected to be in Cannabis as all living plants are known to produce and metabolize it.

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

168.04

Monoisotopic Molecular Weight

167.9824

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

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

Placenta

Organ and components:

Prostate

Biofluid and excreta:

Subcellular:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Phosphoenolpyruvic acid, non-derivatized, GC-MS Spectrum	splash10-0292-0962000000-44d3914b4e07e5c50e3f	Spectrum
GC-MS	Phosphoenolpyruvic acid, non-derivatized, GC-MS Spectrum	splash10-0292-0962000000-44d3914b4e07e5c50e3f	Spectrum
Predicted GC-MS	Phosphoenolpyruvic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0002-9200000000-ae9d81fc88a98f678268	Spectrum
Predicted GC-MS	Phosphoenolpyruvic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9410000000-072478606f0ab6809902	Spectrum
Predicted GC-MS	Phosphoenolpyruvic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phosphoenolpyruvic acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phosphoenolpyruvic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Phosphoenolpyruvic acid, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udr-1900000000-9a4f5554af9a717d99c7	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000x-9200000000-6cdc15f3daa25fc41655	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-001i-9100000000-39e22409d6d924a774f1	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00xu-0912000000-ad1823470675975d5ff0	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-1f5b761ce5fa374b0f8e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-d279f0ca2accb130181f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0920000000-f084dccf78e11c8760d7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-00lr-0911000000-7fa833698210746c838f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-000i-9000000000-62e28301f20b08971b78	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0udi-0900000000-25f970898112f7b89898	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Positive	splash10-0002-0930000000-58691b23d317c2418c33	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-00p0-0493110000-9d61bb13ab5261fdf9fd	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-004i-9100000000-db409b3cfa9ebabbcb58	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4j-5090000000-1ee56bc4866301d4bf2e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negative	splash10-0a4i-0090000000-bce08b01d44391bfecad	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-016r-7900000000-ffd3b8dcd65aaea26ac3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-9000000000-ceae3587b1e7d8b3da27	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-9000000000-701a17330cd18255d625	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-9000000000-a4178ce4951e2c3dba7b	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-9000000000-9d0421620a7aaa9ef33f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0k9i-1900000000-fb12ade375a7ac97f150	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0f76-8900000000-7f57e6a8e72e5992cd88	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-000j-9300000000-c02bca019150d572b3bc	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-05bf-9200000000-73fa5ca52ecc17bac380	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0079-9300000000-231346190165f44f28dc	2012-08-31	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
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)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Glycolysis
Gluconeogenesis
Pyruvate Metabolism
Amino Sugar Metabolism
Sialuria or French Type Sialuria		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Sialic acid synthase	NANS	9p24.1-p23	Q9NR45	details
6-phosphofructokinase type C	PFKP	10p15.3-p15.2	Q01813	details
6-phosphofructokinase, liver type	PFKL	21q22.3	P17858	details
6-phosphofructokinase, muscle type	PFKM	12q13.3	P08237	details
Pyruvate kinase isozymes M1/M2	PKM	15q22	P14618	details
Pyruvate kinase isozymes R/L	PKLR	1q21	P30613	details
Phosphoenolpyruvate carboxykinase [GTP], mitochondrial	PCK2	14q11.2	Q16822	details
Phosphoenolpyruvate carboxykinase, cytosolic [GTP]	PCK1	20q13.31	P35558	details
Beta-enolase	ENO3	17pter-p11	P13929	details
Gamma-enolase	ENO2	12p13	P09104	details
Alpha-enolase	ENO1	1p36.2	P06733	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Solute carrier organic anion transporter family member 2A1	SLCO2A1	3q21	Q92959	details

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
6-phosphofructokinase type C	PFKP	10p15.3-p15.2	Q01813	details
6-phosphofructokinase, liver type	PFKL	21q22.3	P17858	details
6-phosphofructokinase, muscle type	PFKM	12q13.3	P08237	details
Pyruvate kinase isozymes M1/M2	PKM	15q22	P14618	details
Pyruvate kinase isozymes R/L	PKLR	1q21	P30613	details
Phosphoenolpyruvate carboxykinase [GTP], mitochondrial	PCK2	14q11.2	Q16822	details
Beta-enolase	ENO3	17pter-p11	P13929	details
Gamma-enolase	ENO2	12p13	P09104	details
Alpha-enolase	ENO1	1p36.2	P06733	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Gamma-enolase	ENO2	12p13	P09104	details

Transcriptional Factors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Alpha-enolase	ENO1	1p36.2	P06733	details

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000263

DrugBank ID

DB01819

Phenol Explorer Compound ID

Not Available

FoodDB 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

General References

Not Available

Only showing the first 10 proteins. There are 23 proteins in total.

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Enzymes

Enzyme Details

1. Sialic acid synthase

General function:: Involved in catalytic activity
Specific function:: Produces N-acetylneuraminic acid (Neu5Ac) and 2-keto-3-deoxy-D-glycero-D-galacto-nononic acid (KDN). Can also use N-acetylmannosamine 6-phosphate and mannose 6-phosphate as substrates to generate phosphorylated forms of Neu5Ac and KDN, respectively.
Gene Name:: NANS
Uniprot ID:: Q9NR45
Molecular weight:: 40307.26

Enzyme Details

2. 6-phosphofructokinase type C

General function:: Involved in 6-phosphofructokinase activity
Specific function:: Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:: PFKP
Uniprot ID:: Q01813
Molecular weight:: 85595.405

Enzyme Details

3. 6-phosphofructokinase, liver type

General function:: Involved in 6-phosphofructokinase activity
Specific function:: Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:: PFKL
Uniprot ID:: P17858
Molecular weight:: 85017.825

Enzyme Details

4. 6-phosphofructokinase, muscle type

General function:: Involved in 6-phosphofructokinase activity
Specific function:: Catalyzes the third step of glycolysis, the phosphorylation of fructose-6-phosphate (F6P) by ATP to generate fructose-1,6-bisphosphate (FBP) and ADP.
Gene Name:: PFKM
Uniprot ID:: P08237
Molecular weight:: 85181.925

Enzyme Details

5. Pyruvate kinase isozymes M1/M2

General function:: Involved in magnesium ion binding
Specific function:: Glycolytic enzyme that catalyzes the transfer of a phosphoryl group from phosphoenolpyruvate (PEP) to ADP, generating ATP. Stimulates POU5F1-mediated transcriptional activation. Plays a general role in caspase independent cell death of tumor cells. The ratio betwween the highly active tetrameric form and nearly inactive dimeric form determines whether glucose carbons are channeled to biosynthetic processes or used for glycolytic ATP production. The transition between the 2 forms contributes to the control of glycolysis and is important for tumor cell proliferation and survival.
Gene Name:: PKM
Uniprot ID:: P14618
Molecular weight:: 65930.14

Enzyme Details

6. Pyruvate kinase isozymes R/L

General function:: Involved in magnesium ion binding
Specific function:: Plays a key role in glycolysis (By similarity).
Gene Name:: PKLR
Uniprot ID:: P30613
Molecular weight:: 61829.575

Enzyme Details

7. Phosphoenolpyruvate carboxykinase [GTP], mitochondrial

General function:: Involved in phosphoenolpyruvate carboxykinase activity
Specific function:: Catalyzes the 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 (By similarity).
Gene Name:: PCK2
Uniprot ID:: Q16822
Molecular weight:: 47563.34

Enzyme Details

8. Phosphoenolpyruvate carboxykinase, cytosolic [GTP]

General function:: Involved in phosphoenolpyruvate carboxykinase activity
Specific function:: Catalyzes the 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.
Gene Name:: PCK1
Uniprot ID:: P35558
Molecular weight:: 69193.975

Enzyme Details

9. Beta-enolase

General function:: Involved in magnesium ion binding
Specific function:: Appears to have a function in striated muscle development and regeneration.
Gene Name:: ENO3
Uniprot ID:: P13929
Molecular weight:: 42248.03

Enzyme Details

10. Gamma-enolase

General function:: Involved in magnesium ion binding
Specific function:: Has neurotrophic and neuroprotective properties on a broad spectrum of central nervous system (CNS) neurons. Binds, in a calcium-dependent manner, to cultured neocortical neurons and promotes cell survival (By similarity).
Gene Name:: ENO2
Uniprot ID:: P09104
Molecular weight:: 47268.125

Transporters

Enzyme Details

1. Solute carrier organic anion transporter family member 2A1

General function:: Not Available
Specific function:: May mediate the release of newly synthesized prostaglandins from cells, the transepithelial transport of prostaglandins, and the clearance of prostaglandins from the circulation. Transports PGD2, as well as PGE1, PGE2 and PGF2A
Gene Name:: SLCO2A1
Uniprot ID:: Q92959
Molecular weight:: 70117.0

Only showing the first 10 proteins. There are 23 proteins in total.

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Showing Compound Card for Phosphoenolpyruvic acid (CDB005089)

Structure for CDB005089 (Phosphoenolpyruvic acid)

Enzymes

Transporters