Livestock Metabolome Database: Showing metabocard for O-Phosphoethanolamine (LMDB00104)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:42:27 UTC

Update Date

2016-07-20 20:25:06 UTC

Lmdb

LMDB00104

Secondary Accession Numbers

None

Metabolite Identification

Common Name

O-Phosphoethanolamine

Description

Phosphoethanolamine (PE) is a phosphomonoester metabolite of the phospholipid metabolism. PE is a precursor of phospholipid synthesis and a product of phospholipid breakdown. Phosphomonoesters are present at much higher levels in brain than in other organs. In developing brain, phosphomonoesters are normally elevated during the period of neuritic proliferation. This also coincides with the occurrence of normal programmed cell death and synaptic pruning in developing brain. These findings are consistent with the role of phosphomonoesters in membrane biosynthesis. PE shows a strong structural similarity to the inhibitory neurotransmitter, GABA, and the GABAB receptor partial agonist, 3-amino-propylphosphonic acid. PE is a phosphomonoester which is decreased in post-mortem Alzheimer's disease (AD) brain. (PMID: 7791524 , 8588821 , 11566853 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Amino-ethanol dihydrogen phosphate	ChEBI
2-Amino-ethanol phosphate	ChEBI
Colamine phosphate	ChEBI
Colamine phosphoric acid	ChEBI
Colaminphosphoric acid	ChEBI
EAP	ChEBI
Ethanolamine acid phosphate	ChEBI
Ethanolamine O-phosphate	ChEBI
Ethanolamine phosphate	ChEBI
mono(2-Aminoethyl) phosphate	ChEBI
Monoaminoethyl phosphate	ChEBI
O-Phosphocolamine	ChEBI
O-Phosphorylethanolamine	ChEBI
OPE	ChEBI
PE	ChEBI
PEA	ChEBI
PETN	ChEBI
Phosphoethanolamine	ChEBI
Phosphoric acid 2-aminoethyl phenyl ester	ChEBI
Phosphoryl-ethanolamine	ChEBI
2-Amino-ethanol dihydrogen phosphoric acid	Generator
2-Amino-ethanol phosphoric acid	Generator
Colaminphosphate	Generator
Ethanolamine acid phosphoric acid	Generator
Ethanolamine O-phosphoric acid	Generator
Ethanolamine phosphoric acid	Generator
mono(2-Aminoethyl) phosphoric acid	Generator
Monoaminoethyl phosphoric acid	Generator
Phosphate 2-aminoethyl phenyl ester	Generator
Phosphonoethanolamine	HMDB
2-Amino-ethanol dihydrogen phosphate (ester)	HMDB
2-Aminoethanol O-phosphate	HMDB
2-Aminoethyl dihydrogen phosphate	HMDB
2-Aminoethyl dihydrogen phosphate (acd/name 4.0)	HMDB
2-Aminoethyl phosphate	HMDB
Colamine acid phosphate	HMDB
Colaminephosphoric acid	HMDB
Ethamp	HMDB
O-Phosphonatoethanaminium	HMDB
Phosphoryethanolamine	HMDB
Phosphorylethanolamine	HMDB
Phosphorylethanolamine, 3H-labeled CPD	HMDB
Phosphorylethanolamine magnesium (1:1) salt	HMDB
Phosphorylethanolamine zinc salt	HMDB
Phosphorylethanolamine, cobalt (2+) (1:1) salt	HMDB
Calcium 2-aminoethanol phosphate	HMDB
Phosphorylethanolamine ca (1:1) salt	HMDB

Chemical Formula

C₂H₈NO₄P

Average Molecular Weight

141.063

Monoisotopic Molecular Weight

141.019094261

IUPAC Name

(2-aminoethoxy)phosphonic acid

Traditional Name

phosphorylethanolamine

CAS Registry Number

1071-23-4

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 Key

SUHOOTKUPISOBE-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.

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 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

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

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Follicular Fluid
Lung
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Follicular Fluid	Detected and Quantified	22 +/- 2-42+/-4 uM	Not Available	Porcine	183842	details
Follicular Fluid	Detected and Quantified	29 +/- 4-62+/-1 uM	Not Available	Porcine	183842	details
Lung	Detected but not Quantified	Not Applicable	Not Available	Porcine	23412987	details
Serum	Detected and Quantified	7 +/- 1 uM	Not Available	Porcine	183842	details

External Links

DrugBank ID

DB01738

HMDB ID

HMDB0000224

FooDB ID

FDB031115

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

1485304

BioCyc ID

PHOSPHORYL-ETHANOLAMINE

METLIN ID

5233

PDB ID

Not Available

Wikipedia Link

Phosphorylethanolamine

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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. [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. [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. [11566853 ]

Showing metabocard for O-Phosphoethanolamine (LMDB00104)

Structure for LMDB00104 (O-Phosphoethanolamine)