ChemFOnt: Showing chemical card for Glycerol 1-hexadecanoate (CFc000012276)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 19:00:18 UTC

Chemfont ID

CFc000012276

Molecule Identification

Common Name

Glycerol 1-hexadecanoate

Definition

Glycerol 1-hexadecanoate, also known as alpha-monopalmitin or 1-palmitoylglycerol, is a member of the class of compounds known as 1-monoacylglycerols. 1-Monoacylglycerols are monoacylglycerols containing a glycerol acylated at the 1-position. Thus, glycerol 1-hexadecanoate is considered to be a monoradylglycerol lipid molecule. Glycerol 1-hexadecanoate is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Glycerol 1-hexadecanoate can be found in fats and oils, which makes glycerol 1-hexadecanoate a potential biomarker for the consumption of this food product. Glycerol 1-hexadecanoate can be found in feces and sweat. Glycerol 1-hexadecanoate exists in all living organisms, ranging from bacteria to humans. Glycerol 1-hexadecanoate is a minor component of olive oil and other vegetable oil.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Hexadecanoylglycerol	ChEBI
1-Palmitoylglycerol	ChEBI
2,3-Dihydroxypropyl hexadecanoate	ChEBI
alpha-Monopalmitin	ChEBI
Glycerol 1-monopalmitate	ChEBI
Glycerol 1-palmitate	ChEBI
Glycerol 3-palmitate	ChEBI
Glyceryl palmitate	ChEBI
Hexadecanoic acid, 2,3-dihydroxypropyl ester	ChEBI
Palmitic acid alpha-monoglyceride	ChEBI
Palmitin, 1-mono	ChEBI
2,3-Dihydroxypropyl hexadecanoic acid	Generator
a-Monopalmitin	Generator
Α-monopalmitin	Generator
Glycerol 1-monopalmitic acid	Generator
Glycerol 1-palmitic acid	Generator
Glycerol 3-palmitic acid	Generator
Glyceryl palmitic acid	Generator
Hexadecanoate, 2,3-dihydroxypropyl ester	Generator
Palmitate a-monoglyceride	Generator
Palmitate alpha-monoglyceride	Generator
Palmitate α-monoglyceride	Generator
Palmitic acid a-monoglyceride	Generator
Palmitic acid α-monoglyceride	Generator
Glycerol 1-hexadecanoic acid	Generator
(+-)-2,3-Dihydroxypropyl hexadecanoate	HMDB
(1)-2,3-Dihydroxypropyl palmitate	HMDB
(C16-C22)Trialkyl glyceride	HMDB
(S)-2,3-Dihydroxypropyl palmitate	HMDB
1,2,3-Propanetriol 1-hexandecanoyl ester	HMDB
1-Hexadecanoyl-sn-glycerol	HMDB
1-mono-Palmitin	HMDB
1-Monohexadecanoyl-rac-glycerol	HMDB, MeSH
1-Monohexadecanoylglycerol	HMDB, MeSH
1-Monopalmitin	HMDB, MeSH
1-MONOPALMITOYL-rac-glycerol	HMDB
1-Monopalmitoylglycerol	HMDB
1-O-Hexadecanoylglycerol	HMDB
2,3-Dihydroxypropyl ester(.+/-.)-hexadecanoic acid	HMDB
2,3-Dihydroxypropyl palmitate	HMDB
alpha -Monopalmitin	HMDB
DL-alpha-Palmitin	HMDB
Glycerol 1-monohexadecanoate	HMDB
Glycerol alpha -palmitate	HMDB
Glycerol palmitate	HMDB
Glyceryl monopalmitate	HMDB
Hexadecanoic acid, 2,3-bishydroxy propyl ester	HMDB
Hexadexanoic acid 2,3-dihydroxypropyl ester	HMDB
L-(-)-alpha-Monopalmitin	HMDB
Monopalmitin	HMDB
Palmitic acid alpha -monoglyceride	HMDB
Palmitin, 1-mono- (8ci)	HMDB
Palmitoyl glycerol	HMDB, MeSH
rac-1-Palmitoylglycerol	HMDB
rac-Glycerol 1-palmitate	HMDB
1-Glyceryl hexadecanoate	MeSH
rac-1(3)-Palmitoyl glycerol	MeSH
Palmitoyl glycerol, (+,-)-isomer	MeSH
Palmitoyl glycerol, hexadecanoic-1-(14)C-labeled CPD, (R)-isomer	MeSH
Glycerol-1-monopalmitic acid	Generator

Chemical Formula

C₁₉H₃₈O₄

Average Molecular Weight

330.5026

Monoisotopic Molecular Weight

330.277009704

IUPAC Name

2,3-dihydroxypropyl hexadecanoate

Traditional Name

2,3-dihydroxypropyl hexadecanoate

CAS Registry Number

542-44-9

SMILES

CCCCCCCCCCCCCCCC(=O)OCC(O)CO

InChI Identifier

InChI=1S/C19H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(22)23-17-18(21)16-20/h18,20-21H,2-17H2,1H3

InChI Key

QHZLMUACJMDIAE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-monoacylglycerols. These are monoacylglycerols containing a glycerol acylated at the 1-position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Monoradylglycerols

Direct Parent

1-monoacylglycerols

Alternative Parents

Substituents

1-acyl-sn-glycerol
Fatty acid ester
Fatty acyl
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Alcohol
Organic oxide
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

1-monoglyceride (CHEBI:69081 )
Monoacylglycerols (LMGL01010001 )
a monoacylglycerol (CPD-8508 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Feces (PMID: 27015276)
Urine (PMID: 28157703)
Sweat (HMDB: HMDB0031074)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031074)

Source

Endogenous

Endogenous (HMDB: HMDB0031074)

Animal

Animal (HMDB: HMDB0031074)

Exogenous

Food

Food (HMDB: HMDB0031074)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0031074)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0031074)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0031074)

Lipid metabolism pathway (HMDB: HMDB0031074)

Cellular process

Cell signaling (HMDB: HMDB0031074)

Biochemical process

Lipid transport (HMDB: HMDB0031074)

Role

Biological role

Energy source (HMDB: HMDB0031074)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031074)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.0047 g/L	ALOGPS
logP	5.73	ALOGPS
logP	5.08	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	18	ChemAxon
Refractivity	94.11 m³·mol⁻¹	ChemAxon
Polarizability	42.15 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031074

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB003076

KNApSAcK ID

C00042063

Chemspider ID

14201

KEGG Compound ID

Not Available

BioCyc ID

CPD-8508

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

69081

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Glycerol 1-hexadecanoate (CFc000012276)

MOL for CFc000012276 (Glycerol 1-hexadecanoate)

3D MOL for CFc000012276 (Glycerol 1-hexadecanoate)

3D SDF for CFc000012276 (Glycerol 1-hexadecanoate)

3D-SDF for CFc000012276 (Glycerol 1-hexadecanoate)

PDB for CFc000012276 (Glycerol 1-hexadecanoate)

3D PDB for CFc000012276 (Glycerol 1-hexadecanoate)

SMILES for CFc000012276 (Glycerol 1-hexadecanoate)

INCHI for CFc000012276 (Glycerol 1-hexadecanoate)

Structure for CFc000012276 (Glycerol 1-hexadecanoate)

3D Structure for CFc000012276 (Glycerol 1-hexadecanoate)