Bovine Metabolome Database: Showing metabocard for O-Phosphoethanolamine (BMDB0000224)

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Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (2) Show 2 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:27:00 UTC

Update Date

2020-06-04 20:35:20 UTC

BMDB ID

BMDB0000224

Secondary Accession Numbers

BMDB00224

Metabolite Identification

Common Name

O-Phosphoethanolamine

Description

O-Phosphoethanolamine, also known as colamine phosphoric acid or ethanolamine 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 exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. 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

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

Endogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cytoplasm
Endoplasmic reticulum

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	241 - 243 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	72 mg/mL	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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0fki-0910000000-63541b89e6730018e48b	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (4 TMS)	splash10-0h9a-1921000000-3a1d4ab89b928259f71d	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fki-0910000000-63541b89e6730018e48b	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0h9a-1921000000-3a1d4ab89b928259f71d	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0h9a-1921000000-3a1d4ab89b928259f71d	View in MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0h9a-1921000000-3a1d4ab89b928259f71d	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0fki-0911000000-7fc066f17e2ebf6c84f8	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-000t-9100000000-543d2d90aa663406e999	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-9100000000-993b8efd11624567ec4b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-f2fd3c258685af07afb5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-b479823e7c0ee6b5e03d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-2900000000-9cf72ee86018eb78504f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-9000000000-169b03f94a9f53bd0de4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-9000000000-199d7ab7a4aeb040674e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-9000000000-f573b62dada3630598c3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-9000000000-38c04ce07a85a8db342c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004i-9100000000-b582c6b51602884756da	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-2900000000-9cf72ee86018eb78504f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-169b03f94a9f53bd0de4	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-199d7ab7a4aeb040674e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-f573b62dada3630598c3	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-38c04ce07a85a8db342c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-9100000000-b582c6b51602884756da	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-004i-9000000000-4335e927ba2537543f7d	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - , negative	splash10-004i-9000000000-3e5f10c6e140e555b9fe	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-db65ce46b55b09e54fd2	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-c4e1a40502d86192ed6b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9300000000-a9eb3cce3bf5c7453bd2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-4c92e75f13cc6c5119eb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-5874389316d6cd66936a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002f-9800000000-b5c7c61b118c38407fa5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-b562b8507dff78a49e4d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-dfba6ec4cc15f40c6355	View in MoNA
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-88dc3b66f275af50de34	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 90 MHz, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cytoplasm
Endoplasmic reticulum

Biospecimen Locations

Liver
Mammary Gland
Milk
Placenta
Testis

Pathways

Name	SMPDB/Pathwhiz	KEGG
Phosphatidylcholine Biosynthesis		Not Available
Phosphatidylethanolamine Biosynthesis		Not Available
Phosphatidylcholine Biosynthesis PC(14:0/14:0)		Not Available
Phosphatidylcholine Biosynthesis PC(14:0/14:1(9Z))		Not Available
Phosphatidylcholine Biosynthesis PC(14:0/15:0)		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 23438684	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 28306241	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 29291809	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Testis	Detected and Quantified	6934 +/- 1186 nmol/g of tissue	Not Specified	Not Specified	Normal	Aidin Foroutan, C...	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000224

DrugBank ID

DB01738

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB031115

KNApSAcK ID

Not Available

Chemspider ID

990

KEGG Compound ID

C00346

BioCyc ID

PHOSPHORYL-ETHANOLAMINE

BiGG ID

1485304

Wikipedia Link

Phosphorylethanolamine

METLIN ID

5233

PubChem Compound

1015

PDB ID

Not Available

ChEBI ID

17553

References

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.

Material Safety Data Sheet (MSDS)

Not Available

General References

Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]

Enzymes

Enzyme Details

1. Ethanolamine-phosphate cytidylyltransferase

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Plays an important role in the biosynthesis of the phospholipid phosphatidylethanolamine. Catalyzes the formation of CDP-ethanolamine (By similarity).
Gene Name:: PCYT2
Uniprot ID:: Q5EA75
Molecular weight:: 44158.0

Reactions

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

Enzyme Details

2. SGPL1 protein

General function:: Amino acid transport and metabolism
Specific function:: Not Available
Gene Name:: SGPL1
Uniprot ID:: A5D788
Molecular weight:: 63567.0

Reactions

Sphinganine 1-phosphate → O-Phosphoethanolamine + Palmitaldehyde	details
Sphingosine 1-phosphate → O-Phosphoethanolamine + Palmitaldehyde	details

Showing metabocard for O-Phosphoethanolamine (BMDB0000224)

Structure for BMDB0000224 (O-Phosphoethanolamine)

Enzymes

Reactions

Reactions