ChemFOnt: Showing chemical card for PGF2a ethanolamide (CFc000008519)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:20 UTC

Chemfont ID

CFc000008519

Molecule Identification

Common Name

PGF2a ethanolamide

Definition

PGF2a ethanolamide is a N-acylethanolamine. N-acylethanolamines (NAEs) constitute a class of lipid compounds naturally present in both animal and plant membranes as constituents of the membrane-bound phospholipid, N-acylphosphatidylethanolamine (NAPE). NAPE is composed of a third fatty acid moiety linked to the amino head group of the commonly occurring membrane phospholipid, phosphatidylethanolamine. NAEs are released from NAPE by phospholipase D-type hydrolases in response to a variety of stimuli. Transient NAE release and accumulation has been attributed a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. N-oleoylethanolamine is an inhibitor of the sphingolipid signaling pathway, via specific ceramidase inhibition (ceramidase converts ceramide to sphingosine). N-oleoylethanolamine blocks the effects of TNF- and arachidonic acid on intracellular Ca concentration. (PMID: 12692337 , 12056855 , 12560208 , 11997249 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
N-(9S,11R,15S-Trihydroxy-5Z,13E-prostadienoyl)-ethanolamine	HMDB
PGF2a EA	HMDB
PGF2alpha-EA	HMDB
Prostaglandin F2alpha-ea	HMDB
Prostaglanding F2a ethanolamiden-(8Z,11Z,14Z-icosatrienoyl)-ethanolamide	HMDB
(5E)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-N-(2-hydroxyethyl)hept-5-enimidate	Generator

Chemical Formula

C₂₂H₃₉NO₅

Average Molecular Weight

397.5488

Monoisotopic Molecular Weight

397.282823363

IUPAC Name

(5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-N-(2-hydroxyethyl)hept-5-enamide

Traditional Name

(5E)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxyoct-1-en-1-yl]cyclopentyl]-N-(2-hydroxyethyl)hept-5-enamide

CAS Registry Number

None

SMILES

CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)C[C@H](O)[C@@H]1C\C=C\CCCC(=O)NCCO

InChI Identifier

InChI=1S/C22H39NO5/c1-2-3-6-9-17(25)12-13-19-18(20(26)16-21(19)27)10-7-4-5-8-11-22(28)23-14-15-24/h4,7,12-13,17-21,24-27H,2-3,5-6,8-11,14-16H2,1H3,(H,23,28)/b7-4+,13-12+/t17-,18+,19+,20-,21+/m0/s1

InChI Key

XCVCLIRZZCGEMU-FPLRWIMGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as prostaglandins and related compounds. These are unsaturated carboxylic acids consisting of a 20 carbon skeleton that also contains a five member ring, and are based upon the fatty acid arachidonic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Eicosanoids

Direct Parent

Prostaglandins and related compounds

Alternative Parents

Substituents

Prostaglandin skeleton
N-acylethanolamine
Cyclopentanol
Fatty amide
N-acyl-amine
Cyclic alcohol
Carboxamide group
Secondary carboxylic acid amide
Secondary alcohol
Alkanolamine
Carboxylic acid derivative
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Alcohol
Organonitrogen compound
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0013628)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013628)

Source

Endogenous

Endogenous (HMDB: HMDB0013628)

Animal

Animal (HMDB: HMDB0013628)

Exogenous

Food

Food (HMDB: HMDB0013628)

Exogenous (HMDB: HMDB0013628)

Process

Role

Biological role

Membrane stabilizer (HMDB: HMDB0013628)

Modulator

Immunomodulator (HMDB: HMDB0013628)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013628)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.11 g/L	ALOGPS
logP	2.09	ALOGPS
logP	1.34	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	14.45	ChemAxon
pKa (Strongest Basic)	-0.32	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	110.02 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	113.48 m³·mol⁻¹	ChemAxon
Polarizability	47.34 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0013628

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029605

KNApSAcK ID

Not Available

Chemspider ID

30776717

KEGG Compound ID

C13828

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53481911

PDB ID

Not Available

ChEBI ID

89607

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for PGF2a ethanolamide (CFc000008519)

MOL for CFc000008519 (PGF2a ethanolamide)

3D MOL for CFc000008519 (PGF2a ethanolamide)

3D SDF for CFc000008519 (PGF2a ethanolamide)

3D-SDF for CFc000008519 (PGF2a ethanolamide)

PDB for CFc000008519 (PGF2a ethanolamide)

3D PDB for CFc000008519 (PGF2a ethanolamide)

SMILES for CFc000008519 (PGF2a ethanolamide)

INCHI for CFc000008519 (PGF2a ethanolamide)

Structure for CFc000008519 (PGF2a ethanolamide)

3D Structure for CFc000008519 (PGF2a ethanolamide)