ChemFOnt: Showing chemical card for 9-Hexadecenoylcholine (CFc000008248)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:54:56 UTC

Chemfont ID

CFc000008248

Molecule Identification

Common Name

9-Hexadecenoylcholine

Definition

9-Hexadecenoylcholine, also known as palmitoloelycholine, is a fatty acid-choline and is the ester product of 9-hexadecenoic acid and choline. The pharmacological effects of a series of fatty acid-choline esters have been studied on the isolated rabbit heart, the isolated guinea-pig ileum, and the rat stomach. The effect changed with increasing chain length, and three different types of response were observed. The short-chain compounds produced depression of the isolated rabbit heart and spasm of the isolated guinea-pig ileum. Only one, butyrylcholine, had an erratic stimulating effect on hydrochloric acid secretion by the partially vagotomized rat stomach. Medium-chain compounds had a stimulating effect on the isolated rabbit heart, a mixed spasmogenic and relaxant effect on the isolated guinea-pig ileum, and no effect on the rat stomach. Long-chain compounds blocked the effect of acetylcholine on the isolated rabbit heart and the isolated guinea-pig ileum; they also depressed spontaneous hydrochloric acid secretion by the rat stomach.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₁H₄₂NO₂

Average Molecular Weight

340.5637

Monoisotopic Molecular Weight

340.321554593

IUPAC Name

{2-[(9E)-hexadec-9-enoyloxy]ethyl}trimethylazanium

Traditional Name

{2-[(9E)-hexadec-9-enoyloxy]ethyl}trimethylazanium

CAS Registry Number

943438-47-9

SMILES

CCCCCC\C=C\CCCCCCCC(=O)OCC[N+](C)(C)C

InChI Identifier

InChI=1S/C21H42NO2/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-21(23)24-20-19-22(2,3)4/h10-11H,5-9,12-20H2,1-4H3/q+1/b11-10+

InChI Key

KZSMYKYPFGHWQV-ZHACJKMWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl cholines. These are acylated derivatives of choline. Choline or 2-Hydroxy-N,N,N-trimethylethanaminium is a quaternary ammonium salt with the chemical formula (CH3)3N+(CH2)2OH.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Quaternary ammonium salts

Direct Parent

Acyl cholines

Alternative Parents

Substituents

Acyl choline
Fatty acid ester
Fatty acyl
Tetraalkylammonium salt
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Amine
Organooxygen compound
Organic salt
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Carbonyl group
Organic cation
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Placenta (HMDB: HMDB0013208)

Source

Endogenous

Endogenous (HMDB: HMDB0013208)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.2e-05 g/L	ALOGPS
logP	2.58	ALOGPS
logP	1.9	ChemAxon
logS	-7.5	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	116.9 m³·mol⁻¹	ChemAxon
Polarizability	45.1 Å³	ChemAxon
Number of Rings	0	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

HMDB0013208

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029334

KNApSAcK ID

Not Available

Chemspider ID

14582884

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22155839

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 9-Hexadecenoylcholine (CFc000008248)

MOL for CFc000008248 (9-Hexadecenoylcholine)

3D MOL for CFc000008248 (9-Hexadecenoylcholine)

3D SDF for CFc000008248 (9-Hexadecenoylcholine)

3D-SDF for CFc000008248 (9-Hexadecenoylcholine)

PDB for CFc000008248 (9-Hexadecenoylcholine)

3D PDB for CFc000008248 (9-Hexadecenoylcholine)

SMILES for CFc000008248 (9-Hexadecenoylcholine)

INCHI for CFc000008248 (9-Hexadecenoylcholine)

Structure for CFc000008248 (9-Hexadecenoylcholine)

3D Structure for CFc000008248 (9-Hexadecenoylcholine)