Record Information
Version1.0
Creation date2011-09-21 00:05:01 UTC
Update date2020-09-17 15:38:29 UTC
Primary IDFDB021911
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameO-Phosphoethanolamine
DescriptionO-Phosphoethanolamine, also known as colamine phosphoric acid or ethanolamine O-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 is a very strong basic compound (based on its pKa). O-Phosphoethanolamine exists in all living species, ranging from bacteria to humans. Within humans, O-phosphoethanolamine participates in a number of enzymatic reactions. In particular, O-phosphoethanolamine and palmitaldehyde can be biosynthesized from sphinganine 1-phosphate; which is catalyzed by the enzyme sphingosine-1-phosphate lyase 1. In addition, O-phosphoethanolamine and palmitaldehyde can be biosynthesized from sphingosine 1-phosphate; which is catalyzed by the enzyme sphingosine-1-phosphate lyase 1. In humans, O-phosphoethanolamine is involved in globoid cell leukodystrophy. Outside of the human body, O-Phosphoethanolamine has been detected, but not quantified in, several different foods, such as lambsquarters, nutmegs, yellow wax beans, dandelions, and cloud ear fungus. This could make O-phosphoethanolamine a potential biomarker for the consumption of these foods. The ethanolamine mono-ester of phosphoric acid, and a metabolite of phospholipid metabolism. O-Phosphoethanolamine is a potentially toxic compound.
CAS Number1071-23-4
Structure
Thumb
Synonyms
SynonymSource
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
2-amino-Ethanol ateChEBI
2-amino-Ethanol dihydrogen ateChEBI
2-amino-Ethanol dihydrogen ate (ester)HMDB
2-amino-Ethanol dihydrogen ic acidGenerator
2-amino-Ethanol dihydrogen phosphatehmdb
2-amino-Ethanol dihydrogen phosphate (ester)hmdb
2-amino-Ethanol ic acidGenerator
2-amino-Ethanol phosphatehmdb
2-Aminoethanol O-ateHMDB
2-Aminoethyl ateHMDB
2-Aminoethyl dihydrogen ateHMDB
2-Aminoethyl dihydrogen ate (acd/name 4.0)HMDB
2-aminoethyl dihydrogen phosphatehmdb
2-aminoethyl dihydrogen phosphate (ACD/Name 4.0)hmdb
2-aminoethyl phosphatehmdb
ColaminateGenerator
Colamine acid ateHMDB
Colamine ateChEBI
Colamine ic acidGenerator
Colamine orateGenerator
Colamine oric acidChEBI
Colamineoric acidHMDB
Colaminic acidGenerator
Colaminoric acidChEBI
Ethanolamine acid ateChEBI
Ethanolamine acid ic acidGenerator
Ethanolamine ateChEBI
Ethanolamine ic acidGenerator
Ethanolamine O-ateChEBI
Ethanolamine O-ic acidGenerator
Mono(2-aminoethyl) ateChEBI
Mono(2-aminoethyl) ic acidGenerator
Mono(2-aminoethyl) phosphatehmdb
Monoaminoethyl ateChEBI
Monoaminoethyl ic acidGenerator
O-OcolamineChEBI
O-OethanolamineChEBI
O-OnatoethanaminiumHMDB
O-OrylethanolamineChEBI
O-phosphocolaminehmdb
O-Phosphoethanolaminehmdb
O-phosphorylethanolaminehmdb
OethanolamineChEBI
OnoethanolamineChEBI
Orate 2-aminoethyl phenyl esterGenerator
oric acid 2-Aminoethyl phenyl esterChEBI
OryethanolamineHMDB
Oryl-ethanolamineChEBI
OrylethanolamineHMDB
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC2H8NO4P
IUPAC name(2-aminoethoxy)phosphonic acid
InChI IdentifierInChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)
InChI KeySUHOOTKUPISOBE-UHFFFAOYSA-N
Isomeric SMILESNCCOP(O)(O)=O
Average Molecular Weight141.063
Monoisotopic Molecular Weight141.019094261
Classification
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-001i-9000000000-88dc3b66f275af50de342014-09-20View Spectrum
GC-MSO-Phosphoethanolamine, non-derivatized, GC-MS Spectrumsplash10-0fki-0910000000-63541b89e6730018e48bSpectrum
GC-MSO-Phosphoethanolamine, 4 TMS, GC-MS Spectrumsplash10-0h9a-1921000000-3a1d4ab89b928259f71dSpectrum
GC-MSO-Phosphoethanolamine, non-derivatized, GC-MS Spectrumsplash10-0fki-0910000000-63541b89e6730018e48bSpectrum
GC-MSO-Phosphoethanolamine, non-derivatized, GC-MS Spectrumsplash10-0h9a-1921000000-3a1d4ab89b928259f71dSpectrum
GC-MSO-Phosphoethanolamine, non-derivatized, GC-MS Spectrumsplash10-0h9a-1921000000-3a1d4ab89b928259f71dSpectrum
GC-MSO-Phosphoethanolamine, non-derivatized, GC-MS Spectrumsplash10-0h9a-1921000000-3a1d4ab89b928259f71dSpectrum
GC-MSO-Phosphoethanolamine, non-derivatized, GC-MS Spectrumsplash10-0fki-0911000000-7fc066f17e2ebf6c84f8Spectrum
Predicted GC-MSO-Phosphoethanolamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000t-9100000000-543d2d90aa663406e999Spectrum
Predicted GC-MSO-Phosphoethanolamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-9100000000-993b8efd11624567ec4b2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0006-9000000000-f2fd3c258685af07afb52012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0006-9000000000-b479823e7c0ee6b5e03d2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-2900000000-9cf72ee86018eb78504f2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-9000000000-169b03f94a9f53bd0de42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9000000000-199d7ab7a4aeb040674e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-f573b62dada3630598c32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-38c04ce07a85a8db342c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-004i-9100000000-b582c6b51602884756da2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-2900000000-9cf72ee86018eb78504f2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-169b03f94a9f53bd0de42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-199d7ab7a4aeb040674e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-f573b62dada3630598c32017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-38c04ce07a85a8db342c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-9100000000-b582c6b51602884756da2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-004i-9000000000-4335e927ba2537543f7d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-004i-9000000000-3e5f10c6e140e555b9fe2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-db65ce46b55b09e54fd22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-c4e1a40502d86192ed6b2021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-9300000000-a9eb3cce3bf5c7453bd22015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-4c92e75f13cc6c5119eb2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-5874389316d6cd66936a2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-002f-9800000000-b5c7c61b118c38407fa52015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9100000000-b562b8507dff78a49e4d2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-dfba6ec4cc15f40c63552015-04-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID990
ChEMBL IDCHEMBL146972
KEGG Compound IDC00346
Pubchem Compound ID1015
Pubchem Substance IDNot Available
ChEBI ID17553
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00224
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID1485304
KNApSAcK IDNot Available
HET IDOPE
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDPhosphoethanolamine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Choline/ethanolamine kinaseCHKBQ9Y259
Choline kinase alphaCHKAP35790
Ectonucleotide pyrophosphatase/phosphodiesterase family member 6ENPP6Q6UWR7
Ethanolamine kinase 1ETNK1Q9HBU6
Ethanolamine kinase 2ETNK2Q9NVF9
Sphingosine-1-phosphate lyase 1SGPL1O95470
Ethanolamine-phosphate phospho-lyaseAGXT2L1Q8TBG4
Ethanolamine-phosphate cytidylyltransferasePCYT2Q99447
Pathways
NameSMPDB LinkKEGG Link
Sphingolipid MetabolismSMP00034 map00500
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference