MiMeDB: Showing metabocard for Glycerylphosphorylethanolamine (MMDBc0029472)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:23:40 UTC

Update Date

2022-08-31 10:30:50 UTC

MiMeDB ID

MMDBc0029472

Metabolite Identification

Common 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

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Glycerylphosphorylethanolamine.mol                
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       0.385  -0.667   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.695   0.667   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.925  -0.667   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.925   2.001   0.000  0.00  0.00           O+0
HETATM    5  P   UNK     0      -0.385  -2.001   0.000  0.00  0.00           P+0
HETATM    6  O   UNK     0       0.949  -2.771   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      -1.155  -3.334   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -1.719  -1.231   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -0.385   0.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.925   0.667   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.695  -0.667   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.695   2.001   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.925   3.334   0.000  0.00  0.00           O+0
CONECT    1    3    5    9                                                  
CONECT    2    3    4                                                       
CONECT    3    2    1                                                       
CONECT    4    2                                                            
CONECT    5    6    7    8    1                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5                                                            
CONECT    9   10    1                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

Synonyms

Value	Source
2-Aminoethyl ester 1-glycerophosphoric acid	HMDB
a-Glycerophosphorylethanolamine	HMDB
alpha-Glycerophosphorylethanolamine	HMDB
Glycerol 3-phosphoethanolamine	HMDB, MeSH
Glycerol 3-phosphorylethanolamine	HMDB
Glycerophosphoethanolamine	HMDB
Glycerophosphorylethanolamine	HMDB
Glyceryl-3-phosphorylethanolamine	HMDB
GPEA	HMDB

Chemical Formula

C₅H₁₄NO₆P

Average Molecular Weight

215.1415

Monoisotopic Molecular Weight

215.055873697

IUPAC Name

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

Traditional Name

GPEA

CAS Registry Number

1190-00-7

SMILES

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

InChI Identifier

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)

InChI Key

FRMZOWIQVCBEAC-UHFFFAOYSA-N

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

Functional Ontology

Not Available

Physical Properties

State

Solid

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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-4900000000-8d93f4ff2c22c15490ae	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive	splash10-003s-6689400000-b56cb30807ba61fbab62	2017-10-06	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0980000000-ccf9996fb9ea623d636f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000t-5900000000-e9dcf708a81d199f0315	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0229-7900000000-b5a90feff216d218102a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03dj-1970000000-6ccb8182c976c4e3615b	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9300000000-b9585a246036f404a036	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004l-9300000000-82f714d7d8fc0c0f3d6d	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Proteins

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Related Health Condition	Evidence Type	Measured in Matrix	Data Source	Reference

Microbial Sources

Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
	Proteobacteria	1	Human	Unknown
Fungi	Ascomycota	1	Human Feces	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference	Details

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB		details

External Links

HMDB ID

HMDB0000114

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021895

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22833510

PDB ID

Not Available

ChEBI ID

134287

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for Glycerylphosphorylethanolamine (MMDBc0029472)

MOL for #<Metabolite:0x000055b76e049450>

3D MOL for #<Metabolite:0x000055b76e049450>

3D SDF for #<Metabolite:0x000055b76e049450>

3D-SDF for #<Metabolite:0x000055b76e049450>

PDB for #<Metabolite:0x000055b76e049450>

3D PDB for #<Metabolite:0x000055b76e049450>

SMILES for #<Metabolite:0x000055b76e049450>

INCHI for #<Metabolite:0x000055b76e049450>

Structure for #<Metabolite:0x000055b76e049450>

3D Structure for #<Metabolite:0x000055b76e049450>