Cannabis Compound Database: Showing Compound Card for O-Phosphoethanolamine (CDB004825)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (9) Show 11 proteins XML

Record Information

Version

1.0

Created at

2020-04-17 18:40:39 UTC

Updated at

2020-12-07 19:11:02 UTC

CannabisDB ID

CDB004825

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

O-Phosphoethanolamine

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. Within humans, O-phosphoethanolamine participates in a number of enzymatic reactions. In particular, O-phosphoethanolamine and palmitaldehyde can be biosynthesized from sphinganine 1-phosphate; which is catalyzed by the enzyme sphingosine-1-phosphate lyase 1. In addition, O-phosphoethanolamine and palmitaldehyde can be biosynthesized from sphingosine 1-phosphate; which is catalyzed by the enzyme sphingosine-1-phosphate lyase 1. In humans, O-phosphoethanolamine is involved in globoid cell leukodystrophy. Outside of the human body, O-Phosphoethanolamine has been detected, but not quantified in, several different foods, such as lambsquarters, nutmegs, yellow wax beans, dandelions, and cloud ear fungus. This could make O-phosphoethanolamine a potential biomarker for the consumption of these foods. The ethanolamine mono-ester of phosphoric acid, and a metabolite of phospholipid metabolism. O-Phosphoethanolamine is a potentially toxic compound. O-Phosphoethanolamine is expected to be in Cannabis as all living plants are known to produce and metabolize it.

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

141.06

Monoisotopic Molecular Weight

141.0191

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

Traumatic brain injury

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Tissue and substructures:

Placenta

Biofluid and excreta:

Subcellular:

Physical Properties

State

Not Available

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	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-88dc3b66f275af50de34	2014-09-20	View Spectrum
GC-MS	O-Phosphoethanolamine, non-derivatized, GC-MS Spectrum	splash10-0fki-0910000000-63541b89e6730018e48b	Spectrum
GC-MS	O-Phosphoethanolamine, 4 TMS, GC-MS Spectrum	splash10-0h9a-1921000000-3a1d4ab89b928259f71d	Spectrum
GC-MS	O-Phosphoethanolamine, non-derivatized, GC-MS Spectrum	splash10-0fki-0910000000-63541b89e6730018e48b	Spectrum
GC-MS	O-Phosphoethanolamine, non-derivatized, GC-MS Spectrum	splash10-0h9a-1921000000-3a1d4ab89b928259f71d	Spectrum
GC-MS	O-Phosphoethanolamine, non-derivatized, GC-MS Spectrum	splash10-0h9a-1921000000-3a1d4ab89b928259f71d	Spectrum
GC-MS	O-Phosphoethanolamine, non-derivatized, GC-MS Spectrum	splash10-0h9a-1921000000-3a1d4ab89b928259f71d	Spectrum
GC-MS	O-Phosphoethanolamine, non-derivatized, GC-MS Spectrum	splash10-0fki-0911000000-7fc066f17e2ebf6c84f8	Spectrum
Predicted GC-MS	O-Phosphoethanolamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000t-9100000000-543d2d90aa663406e999	Spectrum
Predicted GC-MS	O-Phosphoethanolamine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-9100000000-993b8efd11624567ec4b	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0006-9000000000-f2fd3c258685af07afb5	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0006-9000000000-b479823e7c0ee6b5e03d	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-2900000000-9cf72ee86018eb78504f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-004i-9000000000-169b03f94a9f53bd0de4	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-004i-9000000000-199d7ab7a4aeb040674e	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-9000000000-f573b62dada3630598c3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-9000000000-38c04ce07a85a8db342c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative	splash10-004i-9100000000-b582c6b51602884756da	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-2900000000-9cf72ee86018eb78504f	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-169b03f94a9f53bd0de4	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-199d7ab7a4aeb040674e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-f573b62dada3630598c3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-004i-9000000000-38c04ce07a85a8db342c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , negative	splash10-004i-9100000000-b582c6b51602884756da	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-004i-9000000000-4335e927ba2537543f7d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , negative	splash10-004i-9000000000-3e5f10c6e140e555b9fe	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-db65ce46b55b09e54fd2	2021-09-20	View Spectrum
MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-c4e1a40502d86192ed6b	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-9300000000-a9eb3cce3bf5c7453bd2	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-9000000000-4c92e75f13cc6c5119eb	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-5874389316d6cd66936a	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002f-9800000000-b5c7c61b118c38407fa5	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9100000000-b562b8507dff78a49e4d	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-dfba6ec4cc15f40c6355	2015-04-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Name	SMPDB/Pathwhiz	KEGG
Sphingolipid Metabolism
Gaucher Disease		Not Available
Globoid Cell Leukodystrophy		Not Available
Metachromatic Leukodystrophy (MLD)		Not Available
Fabry disease		Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Ethanolamine-phosphate cytidylyltransferase	PCYT2	17q25.3	Q99447	details
Choline/ethanolamine kinase	CHKB	22q13.33	Q9Y259	details
Choline kinase alpha	CHKA	11q13.2	P35790	details
Ethanolamine kinase 1	ETNK1	12p12.1	Q9HBU6	details
Sphingosine-1-phosphate lyase 1	SGPL1	10q21	O95470	details
Phosphoethanolamine/phosphocholine phosphatase	PHOSPHO1	17q21.32	Q8TCT1	details
Ethanolamine-phosphate phospho-lyase	AGXT2L1	4q25	Q8TBG4	details
Ethanolamine kinase 2	ETNK2	1q32.1	Q9NVF9	details
Ectonucleotide pyrophosphatase/phosphodiesterase family member 6	ENPP6	4q35.1	Q6UWR7	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Phosphoethanolamine/phosphocholine phosphatase	PHOSPHO1	17q21.32	Q8TCT1	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Sphingosine-1-phosphate lyase 1	SGPL1	10q21	O95470	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0000224

DrugBank ID

DB01738

Phenol Explorer Compound ID

Not Available

FoodDB 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

General References

Not Available

Only showing the first 10 proteins. There are 11 proteins in total.

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Enzymes

Enzyme Details

1. Ethanolamine-phosphate cytidylyltransferase

General function:: Involved in catalytic activity
Specific function:: Plays an important role in the biosynthesis of the phospholipid phosphatidylethanolamine. Catalyzes the formation of CDP-ethanolamine.
Gene Name:: PCYT2
Uniprot ID:: Q99447
Molecular weight:: 35199.52

Enzyme Details

2. Choline/ethanolamine kinase

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Has a key role in phospholipid biosynthesis. Catalyzes the first step in phosphatidylethanolamine biosynthesis. Phosphorylates ethanolamine, and can also act on choline (in vitro). Has higher activity with ethanolamine. May not significantly contribute to in vivo phosphatidylcholine biosynthesis.
Gene Name:: CHKB
Uniprot ID:: Q9Y259
Molecular weight:: 45270.99

Enzyme Details

3. Choline kinase alpha

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Has a key role in phospholipid biosynthesis and may contribute to tumor cell growth. Catalyzes the first step in phosphatidylcholine biosynthesis. Contributes to phosphatidylethanolamine biosynthesis. Phosphorylates choline and ethanolamine. Has higher activity with choline.
Gene Name:: CHKA
Uniprot ID:: P35790
Molecular weight:: 52248.53

Enzyme Details

4. Ethanolamine kinase 1

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Highly specific for ethanolamine phosphorylation. May be a rate-controlling step in phosphatidylethanolamine biosynthesis.
Gene Name:: ETNK1
Uniprot ID:: Q9HBU6
Molecular weight:: 27994.955

Enzyme Details

5. Sphingosine-1-phosphate lyase 1

General function:: Involved in carboxy-lyase activity
Specific function:: Cleaves phosphorylated sphingoid bases (PSBs), such as sphingosine-1-phosphate, into fatty aldehydes and phosphoethanolamine. Elevates stress-induced ceramide production and apoptosis.
Gene Name:: SGPL1
Uniprot ID:: O95470
Molecular weight:: 63523.265

Enzyme Details

6. Phosphoethanolamine/phosphocholine phosphatase

General function:: Involved in phosphatase activity
Specific function:: Phosphatase that has a high activity toward phosphoethanolamine (PEA) and phosphocholine (PCho). Involved in the generation of inorganic phosphate for bone mineralization.
Gene Name:: PHOSPHO1
Uniprot ID:: Q8TCT1
Molecular weight:: 32350.505

Enzyme Details

7. Ethanolamine-phosphate phospho-lyase

General function:: Involved in transaminase activity
Specific function:: Catalyzes the pyridoxal-phosphate-dependent breakdown of phosphoethanolamine, converting it to ammonia, inorganic phosphate and acetaldehyde.
Gene Name:: AGXT2L1
Uniprot ID:: Q8TBG4
Molecular weight:: 55039.64

Enzyme Details

8. Ethanolamine kinase 2

General function:: Cell wall/membrane/envelope biogenesis
Specific function:: Highly specific for ethanolamine phosphorylation. Does not have choline kinase activity (By similarity).
Gene Name:: ETNK2
Uniprot ID:: Q9NVF9
Molecular weight:: 44781.125

Enzyme Details

9. Ectonucleotide pyrophosphatase/phosphodiesterase family member 6

General function:: Involved in catalytic activity
Specific function:: Choline-specific glycerophosphodiester phosphodiesterase. The preferred substrate may be lysosphingomyelin (By similarity). Hydrolyzes lysophosphatidylcholine (LPC) to form monoacylglycerol and phosphorylcholine but not lysophosphatidic acid, showing it has a lysophospholipase C activity. Has a preference for LPC with short (12:0 and 14:0) or polyunsaturated (18:2 and 20:4) fatty acids. Also hydrolyzes glycerophosphorylcholine and sphingosylphosphorylcholine efficiently. Hydrolyzes the classical substrate for phospholipase C, p-nitrophenyl phosphorylcholine in vitro, while it does not hydrolyze the classical nucleotide phosphodiesterase substrate, p-nitrophenyl thymidine 5'-monophosphate. Does not hydrolyze diacyl phospholipids such as phosphatidylethanolamine, phosphatidylinositol, phosphatidylserine, phosphatidylglycerol and phosphatidic acid.
Gene Name:: ENPP6
Uniprot ID:: Q6UWR7
Molecular weight:: 50240.625

Only showing the first 10 proteins. There are 11 proteins in total.

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Showing Compound Card for O-Phosphoethanolamine (CDB004825)

Structure for CDB004825 (O-Phosphoethanolamine)

Enzymes