MiMeDB: Showing metabocard for Glycerol 1-hexadecanoate (MMDBc0000667)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:52:18 UTC

Update Date

2024-10-17 08:06:32 UTC

Metabolite ID

MMDBc0000667

Metabolite Identification

Common Name

Glycerol 1-hexadecanoate

Description

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

Molecular Formula

C₁₉H₃₈O₄

Average Mass

330.5026

Monoisotopic Mass

330.277009704

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

Not Available

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

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	1	Human ; Human mucosa; Human supragingival plaque; Human subgingival plaque; Human saliva	Indirect association between microbiota composition and metabolites measured in host biospecimen
Eukaryota/Fungi	Ascomycota	1

Exposure Sources

Source Type	Activity	Data Source	Reference
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

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

General References

Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. doi: 10.1096/fasebj.11.1.9034165. [PubMed:9034165 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. doi: 10.1194/jlr.R600022-JLR200. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Glycerol 1-hexadecanoate (MMDBc0000667)

MOL for #<Metabolite:0x00007fdb07d4af78>

3D MOL for #<Metabolite:0x00007fdb07d4af78>

3D SDF for #<Metabolite:0x00007fdb07d4af78>

3D-SDF for #<Metabolite:0x00007fdb07d4af78>

PDB for #<Metabolite:0x00007fdb07d4af78>

3D PDB for #<Metabolite:0x00007fdb07d4af78>

SMILES for #<Metabolite:0x00007fdb07d4af78>

INCHI for #<Metabolite:0x00007fdb07d4af78>

Structure for #<Metabolite:0x00007fdb07d4af78>

3D Structure for #<Metabolite:0x00007fdb07d4af78>