O-Phosphoethanolamine (YMDB00125)

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Identification

YMDB ID

YMDB00125

Name

O-Phosphoethanolamine

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

Description

O-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. O-Phosphoethanolamine is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

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 number

1071-23-4

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)

IUPAC Name

(2-aminoethoxy)phosphonic acid

Traditional IUPAC Name

phosphorylethanolamine

Chemical Formula

C₂H₈NO₄P

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.

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 )

Physical Properties

State

Solid

Charge

Melting point

241-243 °C

Experimental Properties

Property	Value	Reference
Water Solubility	72 mg/mL [HMP experimental]	PhysProp
LogP	Not Available	PhysProp

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	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

endoplasmic reticulum
cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Glycerophospholipid metabolism	PW002493
Sphingolipid metabolism	PW002479

KEGG Pathways

Glycerophospholipid metabolism	ec00564
Sphingolipid metabolism	ec00600

SMPDB Reactions

Sphinganine 1-phosphate → O-Phosphoethanolamine + Palmitaldehyde

Sphingosine 1-phosphate → O-Phosphoethanolamine + Palmitaldehyde

O-Phosphoethanolamine + hydron + Cytidine triphosphate → CDP-Ethanolamine + Pyrophosphate

Ethanolamine + Adenosine triphosphate → ADP + hydron + O-Phosphoethanolamine

KEGG Reactions

Adenosine triphosphate + Ethanolamine → hydron + ADP + O-Phosphoethanolamine

hydron + Cytidine triphosphate + O-Phosphoethanolamine → Pyrophosphate + CDP-Ethanolamine

Phytosphingosine 1-phosphate → 2-hydroxyhexadecanal + O-Phosphoethanolamine

Sphinganine 1-phosphate → Palmitaldehyde + O-Phosphoethanolamine

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

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	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0h9a-1921000000-3a1d4ab89b928259f71d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fki-0910000000-63541b89e6730018e48b	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0h9a-1921000000-3a1d4ab89b928259f71d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0h9a-1921000000-3a1d4ab89b928259f71d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0h9a-1921000000-3a1d4ab89b928259f71d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fki-0911000000-7fc066f17e2ebf6c84f8	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000t-9100000000-543d2d90aa663406e999	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-9100000000-993b8efd11624567ec4b	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-f2fd3c258685af07afb5	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-b479823e7c0ee6b5e03d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-2900000000-9cf72ee86018eb78504f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-9000000000-169b03f94a9f53bd0de4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-9000000000-199d7ab7a4aeb040674e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-9000000000-f573b62dada3630598c3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-9000000000-38c04ce07a85a8db342c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004i-9100000000-b582c6b51602884756da	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-2900000000-9cf72ee86018eb78504f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-169b03f94a9f53bd0de4	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-199d7ab7a4aeb040674e	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-f573b62dada3630598c3	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-38c04ce07a85a8db342c	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-9100000000-b582c6b51602884756da	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-004i-9000000000-4335e927ba2537543f7d	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-004i-9000000000-3e5f10c6e140e555b9fe	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-db65ce46b55b09e54fd2	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-c4e1a40502d86192ed6b	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9300000000-a9eb3cce3bf5c7453bd2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-4c92e75f13cc6c5119eb	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-5874389316d6cd66936a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002f-9800000000-b5c7c61b118c38407fa5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-b562b8507dff78a49e4d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-dfba6ec4cc15f40c6355	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-88dc3b66f275af50de34	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	17553
HMDB ID	HMDB00224
Pubchem Compound ID	1015
Kegg ID	C00346
ChemSpider ID	990
FOODB ID	FDB031115
Wikipedia	Phosphoethanolamine
BioCyc ID	PHOSPHORYL-ETHANOLAMINE

Enzymes

Protein Details

1. Ethanolamine kinase

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.

Protein Details

2. Choline kinase

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.

Protein Details

3. Ethanolamine-phosphate cytidylyltransferase

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.

Protein Details

4. Sphingosine-1-phosphate lyase

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.

Structure for #<Compound:0xa2575740>

Enzymes

Reactions

Reactions

Reactions

Reactions