ECMDB: Glycerylphosphorylethanolamine (ECMDB00114) (M2MDB000042)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (8)Transporters (8)XML

Proteins (590)

Record Information

Version

2.0

Creation Date

2012-05-31 09:57:35 -0600

Update Date

2015-06-03 15:53:12 -0600

Secondary Accession Numbers

ECMDB00114

Identification

Name:

Glycerylphosphorylethanolamine

Description

Glycerylphosphorylethanolamine is membrane breakdown product resulting from the cleavage of the lipid group from glycerophosphoethanlomine fatty acids (i.e. phosphatidylethanolamine). Phosphatidylethanolamine is one of the major lipid constituents of E. coli.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

2-Aminoethyl ester 1-glycerophosphate
2-Aminoethyl ester 1-Glycerophosphorate
2-Aminoethyl ester 1-Glycerophosphoric acid
A-Glycerophosphorylethanolamine
Alpha-Glycerophosphorylethanolamine
Glycerol 3-phosphoethanolamine
Glycerol 3-phosphorylethanolamine
Glycerophosphoethanolamine
Glycerophosphorylethanolamine
Glyceryl-3-phosphorylethanolamine
Glycerylphosphorylethanolamine
GPEA
α-Glycerophosphorylethanolamine

Chemical Formula:

C₅H₁₄NO₆P

Weight:

Average: 215.1415
Monoisotopic: 215.055873697

InChI Key:

FRMZOWIQVCBEAC-UHFFFAOYSA-N

InChI:

InChI=1S/C5H14NO6P/c7-2-1-6(13(10,11)12)3-5(9)4-8/h5,7-9H,1-4H2,(H2,10,11,12)

CAS number:

1190-00-7

IUPAC Name:

[(2,3-dihydroxypropyl)(2-hydroxyethyl)amino]phosphonic acid

Traditional IUPAC Name:

GPEA

SMILES:

OCCN(CC(O)CO)P(O)(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as organic phosphoramides. These are organic compounds containing the phosphoric acid amide functional group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Organic phosphoric acids and derivatives

Sub Class

Organic phosphoramides

Direct Parent

Organic phosphoramides

Alternative Parents

Substituents

Organic phosphoric acid amide
Secondary alcohol
Alkanolamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organonitrogen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	29.2 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-3.2	ChemAxon
logS	-0.87	ALOGPS
pKa (Strongest Acidic)	2.8	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	121.46 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	44.53 m³·mol⁻¹	ChemAxon
Polarizability	18.51 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:

Cytoplasm

Reactions:

SMPDB Pathways:

Not Available

KEGG Pathways:

Glycerophospholipid metabolism ec00564

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-4900000000-8d93f4ff2c22c15490ae	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-003s-6689400000-b56cb30807ba61fbab62	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0980000000-ccf9996fb9ea623d636f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000t-5900000000-e9dcf708a81d199f0315	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0229-7900000000-b5a90feff216d218102a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dj-1970000000-6ccb8182c976c4e3615b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9300000000-b9585a246036f404a036	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004l-9300000000-82f714d7d8fc0c0f3d6d	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

References

References:

Fallbrook A, Turenne SD, Mamalias N, Kish SJ, Ross BM: Phosphatidylcholine and phosphatidylethanolamine metabolites may regulate brain phospholipid catabolism via inhibition of lysophospholipase activity. Brain Res. 1999 Jul 10;834(1-2):207-10. Pubmed: 10407117
Jensen JE, Drost DJ, Menon RS, Williamson PC: In vivo brain (31)P-MRS: measuring the phospholipid resonances at 4 Tesla from small voxels. NMR Biomed. 2002 Aug;15(5):338-47. Pubmed: 12203225
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
Kish SJ, Robitaille Y, Ball M, Gilbert J, Deck JH, Chang LJ, Schut L: Glycerophosphoethanolamine concentration is elevated in brain of patients with dominantly inherited olivopontocerebellar atrophy. Neurosci Lett. 1990 Dec 11;120(2):209-11. Pubmed: 2293106
Nelson C, Moffat B, Jacobsen N, Henzel WJ, Stults JT, King KL, McMurtrey A, Vandlen R, Spencer SA: Glycerophosphorylethanolamine (GPEA) identified as an hepatocyte growth stimulator in liver extracts. Exp Cell Res. 1996 Nov 25;229(1):20-6. Pubmed: 8940245
Nitsch RM, Blusztajn JK, Pittas AG, Slack BE, Growdon JH, Wurtman RJ: Evidence for a membrane defect in Alzheimer disease brain. Proc Natl Acad Sci U S A. 1992 Mar 1;89(5):1671-5. Pubmed: 1311847
Perry TL, Hansen S, Gandham SS: Postmortem changes of amino compounds in human and rat brain. J Neurochem. 1981 Feb;36(2):406-10. Pubmed: 7463068
Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411

Synthesis Reference:

Tronconi, Giovanni. Process for the chromatographic isolation of 1-(a)-glycerylphosphorylcholine and of L-(a)-glycerylphosphorylethanolamine. PCT Int. Appl. (1990), 18 pp.

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	134287
HMDB ID	HMDB00114
Pubchem Compound ID	123874
Kegg ID	C01233
ChemSpider ID	17215919
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Lysophospholipase L2

General function:: Lipid transport and metabolism
Specific function:: 2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
Gene Name:: pldB
Uniprot ID:: P07000
Molecular weight:: 38978

Reactions

2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.

Protein Details

2. Glycerophosphoryl diester phosphodiesterase

General function:: Involved in glycerophosphodiester phosphodiesterase activity
Specific function:: Glycerophosphoryl diester phosphodiesterase hydrolyzes deacylated phospholipids to G3P and the corresponding alcohols
Gene Name:: glpQ
Uniprot ID:: P09394
Molecular weight:: 40843

Reactions

A glycerophosphodiester + H(2)O = an alcohol + sn-glycerol 3-phosphate.

Protein Details

3. Acyl-CoA thioesterase I

General function:: Involved in hydrolase activity
Specific function:: Hydrolyzes only long chain acyl thioesters (C12-C18). Specificity similar to chymotrypsin
Gene Name:: tesA
Uniprot ID:: P0ADA1
Molecular weight:: 23622

Reactions

2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.

Protein Details

4. sn-glycerol-3-phosphate import ATP-binding protein UgpC

General function:: Involved in nucleotide binding
Specific function:: Part of the ABC transporter complex UgpABCE involved in sn-glycerol-3-phosphate import. Responsible for energy coupling to the transport system (Probable). Can also transport glycerophosphoryl diesters
Gene Name:: ugpC
Uniprot ID:: P10907
Molecular weight:: 39524

Reactions

ATP + H(2)O + glycerol-3-phosphate(Out) = ADP + phosphate + glycerol-3-phosphate(In).

Protein Details

5. Glycerophosphoryl diester phosphodiesterase_

General function:: Involved in glycerophosphodiester phosphodiesterase activity
Specific function:: Glycerophosphoryl diester phosphodiesterase hydrolyzes deacylated phospholipids to G3P and the corresponding alcohols
Gene Name:: ugpQ
Uniprot ID:: P10908
Molecular weight:: 27409

Reactions

A glycerophosphodiester + H(2)O = an alcohol + sn-glycerol 3-phosphate.

Protein Details

6. sn-glycerol-3-phosphate transport system permease protein ugpA

General function:: Involved in transporter activity
Specific function:: Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:: ugpA
Uniprot ID:: P10905
Molecular weight:: 33264

Protein Details

7. sn-glycerol-3-phosphate transport system permease protein ugpE

General function:: Involved in transporter activity
Specific function:: Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:: ugpE
Uniprot ID:: P10906
Molecular weight:: 31499

Protein Details

8. sn-glycerol-3-phosphate-binding periplasmic protein ugpB

General function:: Involved in transporter activity
Specific function:: sn-glycerol-3-phosphate and glycerophosphoryl diester- binding protein interacts with the binding protein-dependent transport system ugpACE
Gene Name:: ugpB
Uniprot ID:: P0AG80
Molecular weight:: 48448

Transporters

Protein Details

1. sn-glycerol-3-phosphate import ATP-binding protein UgpC

General function:: Involved in nucleotide binding
Specific function:: Part of the ABC transporter complex UgpABCE involved in sn-glycerol-3-phosphate import. Responsible for energy coupling to the transport system (Probable). Can also transport glycerophosphoryl diesters
Gene Name:: ugpC
Uniprot ID:: P10907
Molecular weight:: 39524

Reactions

ATP + H(2)O + glycerol-3-phosphate(Out) = ADP + phosphate + glycerol-3-phosphate(In).

Protein Details

2. sn-glycerol-3-phosphate transport system permease protein ugpA

General function:: Involved in transporter activity
Specific function:: Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:: ugpA
Uniprot ID:: P10905
Molecular weight:: 33264

Protein Details

3. sn-glycerol-3-phosphate transport system permease protein ugpE

General function:: Involved in transporter activity
Specific function:: Part of the binding-protein-dependent transport system for sn-glycerol-3-phosphate; probably responsible for the translocation of the substrate across the membrane
Gene Name:: ugpE
Uniprot ID:: P10906
Molecular weight:: 31499

Protein Details

4. Outer membrane protein N

General function:: Involved in transporter activity
Specific function:: Non-specific porin
Gene Name:: ompN
Uniprot ID:: P77747
Molecular weight:: 41220

Protein Details

5. Outer membrane pore protein E

General function:: Involved in transporter activity
Specific function:: Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:: phoE
Uniprot ID:: P02932
Molecular weight:: 38922

Protein Details

6. Outer membrane protein F

General function:: Involved in transporter activity
Specific function:: OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:: ompF
Uniprot ID:: P02931
Molecular weight:: 39333

Protein Details

7. sn-glycerol-3-phosphate-binding periplasmic protein ugpB

General function:: Involved in transporter activity
Specific function:: sn-glycerol-3-phosphate and glycerophosphoryl diester- binding protein interacts with the binding protein-dependent transport system ugpACE
Gene Name:: ugpB
Uniprot ID:: P0AG80
Molecular weight:: 48448

Protein Details

8. Outer membrane protein C

General function:: Involved in transporter activity
Specific function:: Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:: ompC
Uniprot ID:: P06996
Molecular weight:: 40368

Glycerylphosphorylethanolamine (ECMDB00114) (M2MDB000042)

Structure for #<Compound:0xa26447c0>

Enzymes

Reactions

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Transporters

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