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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-04-06 16:21:22 UTC

Update Date

2023-02-21 17:17:45 UTC

HMDB ID

HMDB0012228

Secondary Accession Numbers

HMDB12228

Metabolite Identification

Common Name

Ethylphosphate

Description

Ethylphosphate, also known as MEP, belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain. Ethylphosphate exists in all eukaryotes, ranging from yeast to plants to humans. Ethylphosphate has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make ethylphosphate a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Ethylphosphate.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
MEP	ChEBI
Monoethyl acid phosphate	ChEBI
Monoethyl phosphate	ChEBI
O-Ethyl dihydrogen phosphate	ChEBI
Phosphoric acid monoethyl ester	ChEBI
Monoethyl acid phosphoric acid	Generator
Monoethyl phosphoric acid	Generator
O-Ethyl dihydrogen phosphoric acid	Generator
Phosphate monoethyl ester	Generator
Ethylphosphoric acid	Generator
Ethyl phosphate	HMDB
mono-Ethyl phosphate	HMDB
O-Phosphoric acid triethyl ester	HMDB
EP, organic acid	MeSH, HMDB
Ethyl dihydrogen phosphoric acid	Generator, HMDB
Monoethyl phosphate, disodium salt	MeSH, HMDB
Monoethyl phosphate, zinc salt (1:1)	MeSH, HMDB
Monoethyl phosphate, diammonium salt	MeSH, HMDB
Monoethyl phosphate, dipotassium salt	MeSH, HMDB

Chemical Formula

C₂H₇O₄P

Average Molecular Weight

126.0483

Monoisotopic Molecular Weight

126.008195224

IUPAC Name

ethoxyphosphonic acid

Traditional Name

ethyl dihydrogen phosphate

CAS Registry Number

78-40-0

SMILES

CCOP(O)(O)=O

InChI Identifier

InChI=1S/C2H7O4P/c1-2-6-7(3,4)5/h2H2,1H3,(H2,3,4,5)

InChI Key

ZJXZSIYSNXKHEA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Monoalkyl phosphates

Alternative Parents

Substituents

Monoalkyl phosphate
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

monoalkyl phosphate (CHEBI:42383 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0012228)
Extracellular (HMDB: HMDB0012228)

Source

Exogenous

Exogenous (HMDB: HMDB0012228)

Synthetic

Synthetic (HMDB: HMDB0012228)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0012228)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0012228)

Environmental role

Environmental contaminant (HMDB: HMDB0012228)

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	-56.4 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	0.80	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	29 g/L	ALOGPS
logP	-0.27	ALOGPS
logP	-0.29	ChemAxon
logS	-0.64	ALOGPS
pKa (Strongest Acidic)	1.8	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	23.88 m³·mol⁻¹	ChemAxon
Polarizability	9.82 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	123.127	31661259
DarkChem	[M-H]-	119.097	31661259
DeepCCS	[M+H]+	124.853	30932474
DeepCCS	[M-H]-	122.055	30932474
DeepCCS	[M-2H]-	158.468	30932474
DeepCCS	[M+Na]+	133.024	30932474
AllCCS	[M+H]+	131.2	32859911
AllCCS	[M+H-H2O]+	127.0	32859911
AllCCS	[M+NH4]+	135.1	32859911
AllCCS	[M+Na]+	136.2	32859911
AllCCS	[M-H]-	128.4	32859911
AllCCS	[M+Na-2H]-	132.4	32859911
AllCCS	[M+HCOO]-	136.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.21 minutes	32390414
Predicted by Siyang on May 30, 2022	8.5712 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	6.58 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	354.0 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	532.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	339.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	69.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	235.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	60.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	282.7 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	260.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	596.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	580.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	55.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	615.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	205.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	295.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	648.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	336.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	362.2 seconds	40023050

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Ethylphosphate,1TMS,isomer #1	CCOP(=O)(O)O[Si](C)(C)C	1180.0	Semi standard non polar	33892256
Ethylphosphate,1TMS,isomer #1	CCOP(=O)(O)O[Si](C)(C)C	1085.4	Standard non polar	33892256
Ethylphosphate,1TMS,isomer #1	CCOP(=O)(O)O[Si](C)(C)C	1434.9	Standard polar	33892256
Ethylphosphate,2TMS,isomer #1	CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1211.2	Semi standard non polar	33892256
Ethylphosphate,2TMS,isomer #1	CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1229.2	Standard non polar	33892256
Ethylphosphate,2TMS,isomer #1	CCOP(=O)(O[Si](C)(C)C)O[Si](C)(C)C	1256.5	Standard polar	33892256
Ethylphosphate,1TBDMS,isomer #1	CCOP(=O)(O)O[Si](C)(C)C(C)(C)C	1412.5	Semi standard non polar	33892256
Ethylphosphate,1TBDMS,isomer #1	CCOP(=O)(O)O[Si](C)(C)C(C)(C)C	1312.1	Standard non polar	33892256
Ethylphosphate,1TBDMS,isomer #1	CCOP(=O)(O)O[Si](C)(C)C(C)(C)C	1594.5	Standard polar	33892256
Ethylphosphate,2TBDMS,isomer #1	CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1658.0	Semi standard non polar	33892256
Ethylphosphate,2TBDMS,isomer #1	CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1651.5	Standard non polar	33892256
Ethylphosphate,2TBDMS,isomer #1	CCOP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1560.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Ethylphosphate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-9100000000-1724a6492450cb47d31f	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethylphosphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Ethylphosphate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylphosphate 10V, Positive-QTOF	splash10-002b-9600000000-c613e9eef062d32c1a31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylphosphate 20V, Positive-QTOF	splash10-0002-9000000000-2a19985980166cdd9bf9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylphosphate 40V, Positive-QTOF	splash10-0059-9000000000-dbdb8783e2b8e64f3a3b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylphosphate 10V, Negative-QTOF	splash10-004i-7900000000-83e411c41ce0f8e2ce66	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylphosphate 20V, Negative-QTOF	splash10-004i-9000000000-d6d48cdaf0154a44ca0a	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylphosphate 40V, Negative-QTOF	splash10-004i-9000000000-ca310927ebbed9d63354	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylphosphate 10V, Negative-QTOF	splash10-004i-9000000000-e0c7a786be3374419c0f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylphosphate 20V, Negative-QTOF	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylphosphate 40V, Negative-QTOF	splash10-004i-9000000000-a5e502a2627af2048a1f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylphosphate 10V, Positive-QTOF	splash10-0002-9000000000-a0eaeac3cd0e352aaed1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylphosphate 20V, Positive-QTOF	splash10-0002-9000000000-9afb7f62828d4245d383	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Ethylphosphate 40V, Positive-QTOF	splash10-001i-9000000000-998b23e19de5c0020ddc	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-29	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB03822

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028872

KNApSAcK ID

Not Available

Chemspider ID

66799

KEGG Compound ID

Not Available

BioCyc ID

CPD-8978

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74190

PDB ID

EFS

ChEBI ID

42383

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Morita CT, Beckman EM, Bukowski JF, Tanaka Y, Band H, Bloom BR, Golan DE, Brenner MB: Direct presentation of nonpeptide prenyl pyrophosphate antigens to human gamma delta T cells. Immunity. 1995 Oct;3(4):495-507. [PubMed:7584140 ]

Showing metabocard for Ethylphosphate (HMDB0012228)

MOL for HMDB0012228 (Ethylphosphate)

3D MOL for HMDB0012228 (Ethylphosphate)

3D SDF for HMDB0012228 (Ethylphosphate)

3D-SDF for HMDB0012228 (Ethylphosphate)

PDB for HMDB0012228 (Ethylphosphate)

3D PDB for HMDB0012228 (Ethylphosphate)

SMILES for HMDB0012228 (Ethylphosphate)

INCHI for HMDB0012228 (Ethylphosphate)

Structure for HMDB0012228 (Ethylphosphate)

3D Structure for HMDB0012228 (Ethylphosphate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra