Phosphorylethanolamine

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Description

Phosphorylethanolamine (Monoaminoethyl phosphate) is a membrane phospholipid and an important precursor of Phosphatidylcholine. It is found in most animal tissues and various human extracranial tumors, playing a critical role in membrane integrity, cell division, mitochondrial respiratory function, and more. Studies have shown that changes in the abundance of Phosphorylethanolamine are associated with Alzheimer's disease and Parkinson's disease. Lowering the ratio of Phosphorylethanolamine to Phosphatidylcholine in the liver can improve insulin signaling. Phosphorylethanolamine holds promise for research in the fields of cancer, neurodegenerative disorders, and metabolic diseases[1][2][3][4][5].

CAS Number

1071-23-4

Product Name Alternative

Monoaminoethyl phosphate; NSC 254167; O-Phosphoethanolamine

UNSPSC

12352211

Hazard Statement

H314

Target

Endogenous Metabolite

Type

Natural Products

Related Pathways

Metabolic Enzyme/Protease

Applications

Metabolism-protein/nucleotide metabolism

Field of Research

Cancer; Metabolic Disease; Neurological Disease

Assay Protocol

https://www.medchemexpress.com/Phosphorylethanolamine.html

Purity

99.90

Solubility

H2O : 125 mg/mL (ultrasonic)

Smiles

NCCOP(O)(O)=O

Molecular Formula

C2H8NO4P

Molecular Weight

141.06

Precautions

H314

References & Citations

[1]Kinoshita Y, et al. Phosphorylethanolamine content of human brain tumors. Neurol Med Chir (Tokyo) . 1994 Dec;34 (12) :803-6.|[2]Hui SCN, et al. In vivo spectral editing of phosphorylethanolamine. Magn Reson Med. 2022 Jan;87 (1) :50-56.|[3]Calzada E, et al. Phosphatidylethanolamine Metabolism in Health and Disease. Int Rev Cell Mol Biol. 2016;321:29-88. doi: 10.1016/bs.ircmb.2015.10.001. |[4]van der Veen JN, et al. A role for phosphatidylcholine and phosphatidylethanolamine in hepatic insulin signaling. FASEB J. 2019 Apr;33 (4) :5045-5057.|[5]Nesic I, et al. Alterations in phosphatidylethanolamine levels affect the generation of Aβ. Aging Cell. 2012 Feb;11 (1) :63-72.

Shipping Conditions

Room Temperature

Storage Conditions

-20°C, 3 years; 4°C, 2 years (Powder)

Scientific Category

Natural Products

Clinical Information

No Development Reported

Isoform

Human Endogenous Metabolite; Microbial Metabolite

Chemical Information

Phosphoethanolamine

O-phosphoethanolamine is the ethanolamine mono-ester of phosphoric acid, and a metabolite of phospholipid metabolism. This phosphomonoester shows strong structural similarity to the inhibitory neurotransmitter GABA, and is decreased in post-mortem Alzheimer's disease brain. It has a role as a mouse metabolite, a human metabolite and an algal metabolite. It is a phosphoethanolamine and a primary amino compound. It is a conjugate acid of an O-phosphonatoethanaminium(1-).

CAS Number	1071-23-4
PubChem CID	1015
IUPAC Name	2-aminoethyl dihydrogen phosphate
Molecular Formula	C2H8NO4P
Molecular Weight	141.06
XLogP	-4.8
Topological Polar Surface Area	92.8
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Heavy Atom Count	8
Formal Charge	0
Complexity	98

SMILES

C(COP(=O)(O)O)N

InChI

InChI=1S/C2H8NO4P/c3-1-2-7-8(4,5)6/h1-3H2,(H2,4,5,6)

InChIKey

SUHOOTKUPISOBE-UHFFFAOYSA-N

Chemical Structure

2D Structure

CAS: 1071-23-4

CID: 1015

Formula: C2H8NO4P

MW: 141.06

Interactive 3D Structure

Loading 3D structure...

View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	141.06
XLogP3	-4.8
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	3
Exact Mass	141.01909473
Monoisotopic Mass	141.01909473
Topological Polar Surface Area	92.8 Å²
Heavy Atom Count	8
Formal Charge	0
Complexity	98.2
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

Alternative Products

Catalog	Name
T4881	Phosphorylethanolamine
TRC-P360902-1MG	Phosphorylethanolamine-d4
MBS3609531-01	O-Phosphorylethanolamine
sc-281522A	Cholesteryl-phosphorylethanolamine
sc-300332	Ceramide phosphorylethanolamine
BIB6033	Cholesteryl phosphorylethanolamine

Phosphorylethanolamine

Chemical Information

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