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Record Information
Version1.0
Creation Date2016-09-30 22:27:00 UTC
Update Date2020-05-21 16:27:10 UTC
BMDB IDBMDB0000224
Secondary Accession Numbers
  • BMDB00224
Metabolite Identification
Common NameO-Phosphoethanolamine
DescriptionO-Phosphoethanolamine, also known as colamine phosphoric acid or ethanolamine phosphate, belongs to the class of organic compounds known as phosphoethanolamines. Phosphoethanolamines are compounds containing a phosphate linked to the second carbon of an ethanolamine. O-Phosphoethanolamine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. O-Phosphoethanolamine exists in all living species, ranging from bacteria to humans. O-Phosphoethanolamine is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
2-Amino-ethanol dihydrogen phosphateChEBI
2-Amino-ethanol phosphateChEBI
Colamine phosphateChEBI
Colamine phosphoric acidChEBI
Colaminphosphoric acidChEBI
EAPChEBI
Ethanolamine acid phosphateChEBI
Ethanolamine O-phosphateChEBI
Ethanolamine phosphateChEBI
mono(2-Aminoethyl) phosphateChEBI
Monoaminoethyl phosphateChEBI
O-PhosphocolamineChEBI
O-PhosphorylethanolamineChEBI
OPEChEBI
PEChEBI
PEAChEBI
PETNChEBI
PhosphoethanolamineChEBI
Phosphoric acid 2-aminoethyl phenyl esterChEBI
Phosphoryl-ethanolamineChEBI
2-Amino-ethanol dihydrogen phosphoric acidGenerator
2-Amino-ethanol phosphoric acidGenerator
ColaminphosphateGenerator
Ethanolamine acid phosphoric acidGenerator
Ethanolamine O-phosphoric acidGenerator
Ethanolamine phosphoric acidGenerator
mono(2-Aminoethyl) phosphoric acidGenerator
Monoaminoethyl phosphoric acidGenerator
Phosphate 2-aminoethyl phenyl esterGenerator
PhosphonoethanolamineHMDB
2-Amino-ethanol dihydrogen phosphate (ester)HMDB
2-Aminoethanol O-phosphateHMDB
2-Aminoethyl dihydrogen phosphateHMDB
2-Aminoethyl dihydrogen phosphate (acd/name 4.0)HMDB
2-Aminoethyl phosphateHMDB
Colamine acid phosphateHMDB
Colaminephosphoric acidHMDB
EthampHMDB
O-PhosphonatoethanaminiumHMDB
PhosphoryethanolamineHMDB
PhosphorylethanolamineHMDB
Phosphorylethanolamine, 3H-labeled CPDHMDB
Phosphorylethanolamine magnesium (1:1) saltHMDB
Phosphorylethanolamine zinc saltHMDB
Phosphorylethanolamine, cobalt (2+) (1:1) saltHMDB
Calcium 2-aminoethanol phosphateHMDB
Phosphorylethanolamine ca (1:1) saltHMDB
Chemical FormulaC2H8NO4P
Average Molecular Weight141.063
Monoisotopic Molecular Weight141.019094261
IUPAC Name(2-aminoethoxy)phosphonic acid
Traditional Namephosphorylethanolamine
CAS Registry Number1071-23-4
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 KeySUHOOTKUPISOBE-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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentPhosphoethanolamines
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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Endoplasmic reticulum
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point241 - 243 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility72 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1.5ALOGPS
logP-2.5ChemAxon
logS-0.74ALOGPS
pKa (Strongest Acidic)1.54ChemAxon
pKa (Strongest Basic)10.02ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area92.78 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.08 m³·mol⁻¹ChemAxon
Polarizability11.12 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0fki-0910000000-63541b89e6730018e48bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0h9a-1921000000-3a1d4ab89b928259f71dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fki-0910000000-63541b89e6730018e48bView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0h9a-1921000000-3a1d4ab89b928259f71dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0h9a-1921000000-3a1d4ab89b928259f71dView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0h9a-1921000000-3a1d4ab89b928259f71dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fki-0911000000-7fc066f17e2ebf6c84f8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000t-9100000000-543d2d90aa663406e999View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9100000000-993b8efd11624567ec4bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-f2fd3c258685af07afb5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-b479823e7c0ee6b5e03dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-2900000000-9cf72ee86018eb78504fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-9000000000-169b03f94a9f53bd0de4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9000000000-199d7ab7a4aeb040674eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-f573b62dada3630598c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-38c04ce07a85a8db342cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004i-9100000000-b582c6b51602884756daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-2900000000-9cf72ee86018eb78504fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-169b03f94a9f53bd0de4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-199d7ab7a4aeb040674eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-f573b62dada3630598c3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-38c04ce07a85a8db342cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-9100000000-b582c6b51602884756daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-004i-9000000000-4335e927ba2537543f7dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-004i-9000000000-3e5f10c6e140e555b9feView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9300000000-a9eb3cce3bf5c7453bd2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-4c92e75f13cc6c5119ebView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-5874389316d6cd66936aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-9800000000-b5c7c61b118c38407fa5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-b562b8507dff78a49e4dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-dfba6ec4cc15f40c6355View in MoNA
MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-88dc3b66f275af50de34View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
Biospecimen Locations
  • Liver
  • Mammary Gland
  • Milk
  • Placenta
  • Testis
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
LiverDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
LiverDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
TestisDetected and Quantified6934+/-1186 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • The Bovine Metabo...
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000224
DrugBank IDDB01738
Phenol Explorer Compound IDNot Available
FooDB IDFDB031115
KNApSAcK IDNot Available
Chemspider ID990
KEGG Compound IDC00346
BioCyc IDPHOSPHORYL-ETHANOLAMINE
BiGG ID1485304
Wikipedia LinkPhosphorylethanolamine
METLIN ID5233
PubChem Compound1015
PDB IDNot Available
ChEBI ID17553
References
Synthesis ReferenceMuller K; Schulz J; Oemus R Phosphoethanolamine--a substrate of alkaline phosphatase isolated from rat calvaria. Biomedica biochimica acta (1989), 48(8), 495-504.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  3. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]

Enzymes

General function:
Cell wall/membrane/envelope biogenesis
Specific function:
Plays an important role in the biosynthesis of the phospholipid phosphatidylethanolamine. Catalyzes the formation of CDP-ethanolamine (By similarity).
Gene Name:
PCYT2
Uniprot ID:
Q5EA75
Molecular weight:
44158.0
Reactions
Cytidine triphosphate + O-Phosphoethanolamine → Pyrophosphate + CDP-Ethanolaminedetails
General function:
Amino acid transport and metabolism
Specific function:
Not Available
Gene Name:
SGPL1
Uniprot ID:
A5D788
Molecular weight:
63567.0
Reactions
Sphinganine 1-phosphate → O-Phosphoethanolamine + Palmitaldehydedetails
Sphingosine 1-phosphate → O-Phosphoethanolamine + Palmitaldehydedetails