ContaminantDB: O-Phosphoethanolamine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (1)XML

Record Information

Version

1.0

Creation Date

2014-08-29 06:51:02 UTC

Update Date

2026-05-14 17:14:42 UTC

Accession Number

CHEM003366

Identification

Common Name

O-Phosphoethanolamine

Class

Small Molecule

Description

Phosphoethanolamine (PE) is a phosphomonoester metabolite of the phospholipid metabolism. PE is a precursor of phospholipid synthesis and a product of phospholipid breakdown. Phosphomonoesters are present at much higher levels in brain than in other organs. In developing brain, phosphomonoesters are normally elevated during the period of neuritic proliferation. This also coincides with the occurrence of normal programmed cell death and synaptic pruning in developing brain. These findings are consistent with the role of phosphomonoesters in membrane biosynthesis. PE shows a strong structural similarity to the inhibitory neurotransmitter, GABA, and the GABAB receptor partial agonist, 3-amino-propylphosphonic acid. PE is a phosphomonoester which is decreased in post-mortem Alzheimer's disease (AD) brain. (1, 2, 3).

Contaminant Sources

FooDB Chemicals
HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Amine
Animal Toxin
Ester
Food Toxin
Metabolite
Natural Compound
Organic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-ethanol dihydrogen phosphate	ChEBI
2-Amino-ethanol phosphate	ChEBI
Colamine phosphate	ChEBI
Colamine phosphoric acid	ChEBI
Colaminphosphoric acid	ChEBI
EAP	ChEBI
Ethanolamine acid phosphate	ChEBI
Ethanolamine O-phosphate	ChEBI
Ethanolamine phosphate	ChEBI
mono(2-Aminoethyl) phosphate	ChEBI
Monoaminoethyl phosphate	ChEBI
O-Phosphocolamine	ChEBI
O-Phosphorylethanolamine	ChEBI
OPE	ChEBI
PE	ChEBI
PEA	ChEBI
PETN	ChEBI
Phosphoethanolamine	ChEBI
Phosphoric acid 2-aminoethyl phenyl ester	ChEBI
Phosphoryl-ethanolamine	ChEBI
2-Amino-ethanol dihydrogen phosphoric acid	Generator
2-Amino-ethanol phosphoric acid	Generator
Colaminphosphate	Generator
Ethanolamine acid phosphoric acid	Generator
Ethanolamine O-phosphoric acid	Generator
Ethanolamine phosphoric acid	Generator
mono(2-Aminoethyl) phosphoric acid	Generator
Monoaminoethyl phosphoric acid	Generator
Phosphate 2-aminoethyl phenyl ester	Generator
Phosphonoethanolamine	HMDB
2-Amino-ethanol dihydrogen phosphate (ester)	HMDB
2-Aminoethanol O-phosphate	HMDB
2-Aminoethyl dihydrogen phosphate	HMDB
2-Aminoethyl dihydrogen phosphate (acd/name 4.0)	HMDB
2-Aminoethyl phosphate	HMDB
Colamine acid phosphate	HMDB
Colaminephosphoric acid	HMDB
Ethamp	HMDB
O-Phosphonatoethanaminium	HMDB
Phosphoryethanolamine	HMDB
Phosphorylethanolamine	HMDB
Phosphorylethanolamine, 3H-labeled CPD	HMDB
Phosphorylethanolamine magnesium (1:1) salt	HMDB
Phosphorylethanolamine zinc salt	HMDB
Phosphorylethanolamine, cobalt (2+) (1:1) salt	HMDB
Calcium 2-aminoethanol phosphate	HMDB
Phosphorylethanolamine ca (1:1) salt	HMDB

Chemical Formula

C₂H₈NO₄P

Average Molecular Mass

141.063 g/mol

Monoisotopic Mass

141.019 g/mol

CAS Registry Number

1071-23-4

IUPAC Name

(2-aminoethoxy)phosphonic acid

Traditional Name

phosphorylethanolamine

SMILES

NCCOP(O)(O)=O

InChI Identifier

InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)

InChI Key

SUHOOTKUPISOBE-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phosphoethanolamines. Phosphoethanolamines are compounds containing a phosphate linked to the second carbon of an ethanolamine.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Phosphate esters

Direct Parent

Phosphoethanolamines

Alternative Parents

Substituents

Phosphoethanolamine
Monoalkyl phosphate
Alkyl phosphate
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary amine
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Amine
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

primary amino compound (CHEBI:17553 )
phosphoethanolamine (CHEBI:17553 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Cytoplasm
Endoplasmic reticulum
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Sphingolipid Metabolism	SMP00034	map00600
Hypophosphatasia	SMP00503	Not Available

Applications

Not Available

Biological Roles

human metabolite

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	241 - 243°C
Boiling Point	Not Available
Solubility	72 mg/mL

Predicted Properties

Property	Value	Source
Water Solubility	25.8 g/L	ALOGPS
logP	-1.5	ALOGPS
logP	-2.5	ChemAxon
logS	-0.74	ALOGPS
pKa (Strongest Acidic)	1.54	ChemAxon
pKa (Strongest Basic)	10.02	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	92.78 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	27.08 m³·mol⁻¹	ChemAxon
Polarizability	11.12 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	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	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0fki-0910000000-63541b89e6730018e48b	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0h9a-1921000000-3a1d4ab89b928259f71d	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fki-0910000000-63541b89e6730018e48b	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0h9a-1921000000-3a1d4ab89b928259f71d	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0h9a-1921000000-3a1d4ab89b928259f71d	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0h9a-1921000000-3a1d4ab89b928259f71d	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fki-0911000000-7fc066f17e2ebf6c84f8	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000t-9100000000-543d2d90aa663406e999	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-9100000000-993b8efd11624567ec4b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-f2fd3c258685af07afb5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-b479823e7c0ee6b5e03d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-2900000000-9cf72ee86018eb78504f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-9000000000-169b03f94a9f53bd0de4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-9000000000-199d7ab7a4aeb040674e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-9000000000-f573b62dada3630598c3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-9000000000-38c04ce07a85a8db342c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004i-9100000000-b582c6b51602884756da	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-2900000000-9cf72ee86018eb78504f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-169b03f94a9f53bd0de4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-199d7ab7a4aeb040674e	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-f573b62dada3630598c3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-38c04ce07a85a8db342c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-9100000000-b582c6b51602884756da	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-004i-9000000000-4335e927ba2537543f7d	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-004i-9000000000-3e5f10c6e140e555b9fe	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-db65ce46b55b09e54fd2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-c4e1a40502d86192ed6b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9300000000-a9eb3cce3bf5c7453bd2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-4c92e75f13cc6c5119eb	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-5874389316d6cd66936a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002f-9800000000-b5c7c61b118c38407fa5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-b562b8507dff78a49e4d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-dfba6ec4cc15f40c6355	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-88dc3b66f275af50de34	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum