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Identification
YMDB IDYMDB00125
NameO-Phosphoethanolamine
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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 yeast, O-phosphoethanolamine participates in a number of enzymatic reactions. In particular, O-phosphoethanolamine can be biosynthesized from ethanolamine; which is mediated by the enzyme choline/ethanolamine kinase. In addition, cytidine triphosphate and O-phosphoethanolamine can be converted into CDP-ethanolamine through the action of the enzyme ethanolamine-phosphate cytidylyltransferase. In yeast, O-phosphoethanolamine is involved in the metabolic pathway called phosphatidylcholine biosynthesis pathway. O-Phosphoethanolamine is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 2-amino-Ethanol dihydrogen phosphate
  • 2-amino-Ethanol dihydrogen phosphate (ester)
  • 2-amino-Ethanol phosphate
  • 2-Aminoethanol O-phosphate
  • 2-aminoethyl dihydrogen phosphate
  • 2-aminoethyl phosphate
  • Colamine acid phosphate
  • Colamine phosphate
  • Colamine phosphoric acid
  • Colaminephosphoric acid
  • Colaminphosphoric acid
  • EAP
  • Ethanolamine acid phosphate
  • Ethanolamine O-phosphate
  • Ethanolamine phosphate
  • Mono(2-aminoethyl) phosphate
  • Monoaminoethyl phosphate
  • O-phosphocolamine
  • O-Phosphoethanolamine
  • O-phosphorylethanolamine
  • OPE
  • PETN
  • Phosphoethanolamine
  • Phosphonoethanolamine
  • Phosphoric acid 2-aminoethyl phenyl ester
  • Phosphoryethanolamine
  • Phosphorylethanolamine
  • PE
  • PEA
  • Phosphoryl-ethanolamine
  • 2-Amino-ethanol dihydrogen phosphoric acid
  • 2-Amino-ethanol phosphoric acid
  • Colaminphosphate
  • Ethanolamine acid phosphoric acid
  • Ethanolamine O-phosphoric acid
  • Ethanolamine phosphoric acid
  • mono(2-Aminoethyl) phosphoric acid
  • Monoaminoethyl phosphoric acid
  • Phosphate 2-aminoethyl phenyl ester
  • 2-Aminoethyl dihydrogen phosphate (acd/name 4.0)
  • Ethamp
  • O-Phosphonatoethanaminium
  • Phosphorylethanolamine, 3H-labeled CPD
  • Phosphorylethanolamine magnesium (1:1) salt
  • Phosphorylethanolamine zinc salt
  • Phosphorylethanolamine, cobalt (2+) (1:1) salt
  • Calcium 2-aminoethanol phosphate
  • Phosphorylethanolamine ca (1:1) salt
CAS number1071-23-4
WeightAverage: 141.063
Monoisotopic: 141.019094261
InChI KeySUHOOTKUPISOBE-UHFFFAOYSA-N
InChIInChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)
IUPAC Name(2-aminoethoxy)phosphonic acid
Traditional IUPAC Namephosphorylethanolamine
Chemical FormulaC2H8NO4P
SMILES[H]OP(=O)(O[H])OC([H])([H])C([H])([H])N([H])[H]
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
StateSolid
Charge0
Melting point241-243 °C
Experimental Properties
PropertyValueReference
Water Solubility72 mg/mL [HMP experimental]PhysProp
LogPNot AvailablePhysProp
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
  • endoplasmic reticulum
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
Sphingolipid metabolismPW002479 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerophospholipid metabolismec00564 Map00564
Sphingolipid metabolismec00600 Map00600
SMPDB Reactions
Sphinganine 1-phosphateO-Phosphoethanolamine + Palmitaldehyde
Sphingosine 1-phosphateO-Phosphoethanolamine + Palmitaldehyde
O-Phosphoethanolamine + hydron + Cytidine triphosphateCDP-Ethanolamine + Pyrophosphate
Ethanolamine + Adenosine triphosphateADP + hydron + O-Phosphoethanolamine
KEGG Reactions
Adenosine triphosphate + Ethanolaminehydron + ADP + O-Phosphoethanolamine
hydron + Cytidine triphosphate + O-PhosphoethanolaminePyrophosphate + CDP-Ethanolamine
Phytosphingosine 1-phosphate2-hydroxyhexadecanal + O-Phosphoethanolamine
Sphinganine 1-phosphatePalmitaldehyde + O-Phosphoethanolamine
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Kim, K., Kim, K. H., Storey, M. K., Voelker, D. R., Carman, G. M. (1999). "Isolation and characterization of the Saccharomyces cerevisiae EKI1 gene encoding ethanolamine kinase." J Biol Chem 274:14857-14866.10329685
  • Mao, C., Xu, R., Bielawska, A., Szulc, Z. M., Obeid, L. M. (2000). "Cloning and characterization of a Saccharomyces cerevisiae alkaline ceramidase with specificity for dihydroceramide." J Biol Chem 275:31369-31378.10900202
  • Kim, K. H., Voelker, D. R., Flocco, M. T., Carman, G. M. (1998). "Expression, purification, and characterization of choline kinase, product of the CKI gene from Saccharomyces cerevisiae." J Biol Chem 273:6844-6852.9506987
Synthesis Reference:Muller K; Schulz J; Oemus R Phosphoethanolamine--a substrate of alkaline phosphatase isolated from rat calvaria. Biomedica biochimica acta (1989), 48(8), 495-504.
External Links:
ResourceLink
CHEBI ID17553
HMDB IDHMDB00224
Pubchem Compound ID1015
Kegg IDC00346
ChemSpider ID990
FOODB IDFDB021911
WikipediaPhosphoethanolamine
BioCyc IDPHOSPHORYL-ETHANOLAMINE

Enzymes

General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Catalyzes the committed step of phosphatidylethanolamine synthesis via the CDP-ethanolamine pathway. Also exhibits choline kinase activity but its preferred substrate is ethanolamine
Gene Name:
EKI1
Uniprot ID:
Q03764
Molecular weight:
61656.39844
Reactions
ATP + ethanolamine → ADP + O-phosphoethanolamine.
General function:
Involved in phosphotransferase activity, alcohol group as acceptor
Specific function:
Responsible for phosphatidylcholine synthesis via the CDP-choline pathway. Also exhibits ethanolamine kinase activity but at 14% efficiency compared with choline
Gene Name:
CKI1
Uniprot ID:
P20485
Molecular weight:
66316.0
Reactions
ATP + choline → ADP + O-phosphocholine.
General function:
Involved in catalytic activity
Specific function:
CTP + ethanolamine phosphate = diphosphate + CDP-ethanolamine
Gene Name:
MUQ1
Uniprot ID:
P33412
Molecular weight:
36862.60156
Reactions
CTP + ethanolamine phosphate → diphosphate + CDP-ethanolamine.
General function:
Involved in carboxy-lyase activity
Specific function:
Cleaves phosphorylated sphingoid bases (PSBs), such as sphingosine-1-phosphate, into fatty aldehydes and phosphoethanolamine
Gene Name:
DPL1
Uniprot ID:
Q05567
Molecular weight:
65565.10156
Reactions
Sphinganine 1-phosphate → phosphoethanolamine + palmitaldehyde.