Showing Compound MG(20:4(5Z,8Z,11Z,14Z)/0:0/0:0) (FDB028291)

Record Information

Version

1.0

Creation date

2011-09-21 01:37:28 UTC

Update date

2015-07-21 06:59:22 UTC

Primary ID

FDB028291

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

MG(20:4(5Z,8Z,11Z,14Z)/0:0/0:0)

Description

MG(20:4(5Z,8Z,11Z,14Z)/0:0/0:0) is a monoacylglyceride. A monoglyceride, more correctly known as a monoacylglycerol, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. Monoacylglycerol can be broadly divided into two groups; 1-monoacylglycerols (or 3-monoacylglycerols) and 2-monoacylglycerols, depending on the position of the ester bond on the glycerol moiety. Normally the 1-/3-isomers are not distinguished from each other and are termed 'alpha-monoacylglycerols', while the 2-isomers are beta-monoacylglycerols. Monoacylglycerols are formed biochemically via release of a fatty acid from diacylglycerol by diacylglycerol lipase or hormone sensitive lipase. Monoacylglycerols are broken down by monoacylglycerol lipase. They tend to be minor components only of most plant and animal tissues, and indeed would not be expected to accumulate because their strong detergent properties would have a disruptive effect on membranes. 2-Monoacylglycerols are a major end product of the intestinal digestion of dietary fats in animals via the enzyme pancreatic lipase. They are taken up directly by the intestinal cells and converted to triacylglycerols via the monoacylglycerol pathway before being transported in lymph to the liver. Mono- and Diglycerides are commonly added to commercial food products in small quantities. They act as emulsifiers, helping to mix ingredients such as oil and water that would not otherwise blend well. [HMDB]

CAS Number

124511-15-5

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(S)-Glyceryl 1-arachidonate	ChEBI
(S)-Glyceryl 1-arachidonic acid	Generator
1-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-rac-glycerol	hmdb
1-(5Z,8Z,11Z,14Z-Eicosatetraenoyl)-sn-glycerol	ChEBI
1-AG	hmdb
1-arachidonoyl-glycerol	hmdb
1-Arachidonoyl-sn-glycerol	ChEBI
1-Arachidonoylglycerol	ChEBI
MAG(20:4/0:0)	HMDB
MAG(20:4n6/0:0)	hmdb

Showing 1 to 10 of 14 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.0012 g/L	ALOGPS
logP	5.66	ALOGPS
logP	5.41	ChemAxon
logS	-5.5	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	116.98 m³·mol⁻¹	ChemAxon
Polarizability	45.44 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

Chemical Formula

C23H38O4

IUPAC name

(2S)-2,3-dihydroxypropyl icosa-5,8,11,14-tetraenoate

InChI Identifier

InChI=1S/C23H38O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(26)27-21-22(25)20-24/h6-7,9-10,12-13,15-16,22,24-25H,2-5,8,11,14,17-21H2,1H3/t22-/m0/s1

InChI Key

DCPCOKIYJYGMDN-QFIPXVFZSA-N

Isomeric SMILES

[H][C@](O)(CO)COC(=O)CCCC=CCC=CCC=CCC=CCCCCC

Average Molecular Weight

378.5454

Monoisotopic Molecular Weight

378.277009704

Classification

Description

Belongs to the class of organic compounds known as monoacylglycerols. These are glycerides consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Monoradylglycerols

Direct Parent

Monoacylglycerols

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

Not Available

External Links

ChemSpider ID

13148726

ChEMBL ID

CHEMBL124426

KEGG Compound ID

Not Available

Pubchem Compound ID

16019980

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB11578

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

1AG

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
2-acylglycerol O-acyltransferase 1	MOGAT1	Q96PD6
2-acylglycerol O-acyltransferase 2	MOGAT2	Q3SYC2
2-acylglycerol O-acyltransferase 3	MOGAT3	Q86VF5
Ectonucleotide pyrophosphatase/phosphodiesterase family member 6	ENPP6	Q6UWR7
Lysophosphatidic acid phosphatase type 6	ACP6	Q9NPH0
Monoglyceride lipase	MGLL	Q99685