Record Information
Version2.0
Creation Date2012-08-09 09:16:10 -0600
Update Date2015-09-13 12:56:16 -0600
Secondary Accession Numbers
  • ECMDB21417
Identification
Name:O-Phosphoethanolamine
DescriptionPhosphoethanolamine is chemically the ethanolamine mono-ester of phosphoric acid. It is an important intermediate in the synthesis of LPS. In particular, phosphoethanolamine (pEtN) is added to the outer 3-deoxy-D-manno-octulosonic acid (KDO) residue of a KDO(2)-lipid A via phosphoethanolamine transferase (eptB).
Structure
Thumb
Synonyms:
  • 2-amino-Ethanol dihydrogen phosphate
  • 2-amino-Ethanol dihydrogen phosphate (ester)
  • 2-amino-Ethanol dihydrogen phosphoric acid
  • 2-amino-Ethanol dihydrogen phosphoric acid (ester)
  • 2-amino-Ethanol phosphate
  • 2-amino-Ethanol phosphoric acid
  • 2-Aminoethanol O-phosphate
  • 2-Aminoethanol O-phosphoric acid
  • 2-aminoethyl dihydrogen phosphate
  • 2-aminoethyl dihydrogen phosphate (ACD/Name 4.0)
  • 2-Aminoethyl dihydrogen phosphoric acid
  • 2-Aminoethyl dihydrogen phosphoric acid (acd/name 4.0)
  • 2-aminoethyl phosphate
  • 2-Aminoethyl phosphoric acid
  • Colamine acid phosphate
  • Colamine acid phosphoric acid
  • Colamine phosphate
  • Colamine phosphoric acid
  • Colaminephosphate
  • Colaminephosphoric acid
  • Colaminphosphate
  • Colaminphosphoric acid
  • EAP
  • Ethanolamine acid phosphate
  • Ethanolamine acid phosphoric acid
  • Ethanolamine O-phosphate
  • Ethanolamine O-phosphoric acid
  • Ethanolamine phosphate
  • Ethanolamine phosphoric acid
  • Mono(2-aminoethyl) phosphate
  • mono(2-Aminoethyl) phosphoric acid
  • Monoaminoethyl phosphate
  • Monoaminoethyl phosphoric acid
  • O-phosphocolamine
  • O-phosphoethanolamine
  • O-phosphorylethanolamine
  • OPE
  • PEtN
  • Phosphate 2-aminoethyl phenyl ester
  • Phosphoethanolamine
  • Phosphonoethanolamine
  • Phosphoric acid 2-aminoethyl phenyl ester
  • Phosphoryethanolamine
  • Phosphorylethanolamine
Chemical Formula:C2H8NO4P
Weight:Average: 141.063
Monoisotopic: 141.019094261
InChI Key:SUHOOTKUPISOBE-UHFFFAOYSA-N
InChI:InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)
CAS number:1071-23-4
IUPAC Name:(2-aminoethoxy)phosphonic acid
Traditional IUPAC Name:phosphorylethanolamine
SMILES:NCCOP(O)(O)=O
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
Physical Properties
State:Solid
Charge:-1
Melting point:241-243 °C
Experimental Properties:
PropertyValueSource
Water Solubility:72 mg/mL [HMP experimental]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility25.8 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Lipopolysaccharide biosynthesisPW000831 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Lipopolysaccharide biosynthesis ec00540
EcoCyc Pathways:
  • superpathway of lipopolysaccharide biosynthesis LPSSYN-PWY
Concentrations
Not Available
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-db65ce46b55b09e54fd2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-c4e1a40502d86192ed6bView 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
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
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
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
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
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
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Klunk WE, Debnath ML, McClure RJ, Pettegrew JW: Inactivity of phosphoethanolamine, an endogenous GABA analog decreased in Alzheimer's disease, at GABA binding sites. Life Sci. 1995;56(26):2377-83. Pubmed: 7791524
  • Klunk WE, McClure RJ, Xu CJ, Pettegrew JW: Structural determinants of activity at the GABAB receptor. A comparison of phosphoethanolamine and related GABA analogs. Mol Chem Neuropathol. 1995 Sep;26(1):15-30. Pubmed: 8588821
  • Li G, Foote C, Alexander S, Alexander H: Sphingosine-1-phosphate lyase has a central role in the development of Dictyostelium discoideum. Development. 2001 Sep;128(18):3473-83. Pubmed: 11566853
  • Seki Y, Kimura M, Mizutani N, Fujita M, Aimi Y, Suzuki Y: Cerebrospinal fluid taurine after traumatic brain injury. Neurochem Res. 2005 Jan;30(1):123-8. Pubmed: 15756940
  • Silwood CJ, Lynch E, Claxson AW, Grootveld MC: 1H and (13)C NMR spectroscopic analysis of human saliva. J Dent Res. 2002 Jun;81(6):422-7. Pubmed: 12097436
  • Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 Mar 3. doi: 10.1038/nbt.2488. Pubmed: 23455439
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID17553
HMDB IDHMDB00224
Pubchem Compound ID1015
Kegg IDC00346
ChemSpider ID990
WikipediaPhosphoethanolamine
BioCyc IDPHOSPHORYL-ETHANOLAMINE
EcoCyc IDPHOSPHORYL-ETHANOLAMINE
Ligand ExpoOPE

Enzymes

General function:
Involved in catalytic activity
Specific function:
Catalyzes the addition of a phosphoethanolamine moiety to the lipid A. The phosphoethanolamine modification is required for resistance to polymyxin
Gene Name:
eptA
Uniprot ID:
P30845
Molecular weight:
61667
General function:
Involved in catalytic activity
Specific function:
Catalyzes the addition of a phosphoethanolamine (pEtN) moiety to the outer 3-deoxy-D-manno-octulosonic acid (KDO) residue of a KDO(2)-lipid A. Phosphatidylethanolamines with one unsaturated acyl group functions as pEtN donors and the reaction releases diacylglycerol
Gene Name:
eptB
Uniprot ID:
P37661
Molecular weight:
63804