Showing Compound Glycerol trieicosanoate (FDB000704)

Record Information

Version

1.0

Creation date

2010-04-08 22:04:40 UTC

Update date

2020-09-17 15:36:58 UTC

Primary ID

FDB000704

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Glycerol trieicosanoate

Description

TG(20:0/20:0/20:0) belongs to the family of triradyglycerols, which are glycerolipids lipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. Their general formula is [R1]OCC(CO[R2])O[R3]. TG(20:0/20:0/20:0) is made up of one eicosanoyl(R1), one eicosanoyl(R2), and one eicosanoyl(R3).

CAS Number

620-64-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1-Arachidonyl-2-arachidonyl-3-arachidonyl-glycerol	HMDB
TAG(20:0/20:0/20:0)	HMDB
TAG(60:0)	HMDB
TG(60:0)	HMDB
Tracylglycerol(20:0/20:0/20:0)	HMDB
Tracylglycerol(60:0)	HMDB
Triacylglycerol	HMDB
Triglyceride	HMDB
1-Eicosanoyl-2-eicosanoyl-3-eicosanoyl-glycerol	HMDB
TG(20:0/20:0/20:0)	Lipid Annotator
1,2,3-Propanetriol trieicosanoate	biospider
1,2,3-Propanetriyl trieicosanoate, 9CI	db_source
2,3-Bis(icosanoyloxy)propyl icosanoate	biospider
Eicosanoic acid, 1,2,3-propanetriyl ester	biospider
Glycerol triarachidate	biospider
Glycerol trivalerate	biospider
Glyceryl triarachidate	biospider
Propane-1,2,3-triyl triicosanoate	biospider
Triarachidin	db_source
Triarachin	db_source
Triarachine	biospider

Predicted Properties

Property	Value	Source
Water Solubility	1.1e-05 g/L	ALOGPS
logP	10.67	ALOGPS
logP	24.26	ChemAxon
logS	-7.9	ALOGPS
pKa (Strongest Basic)	-6.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	62	ChemAxon
Refractivity	296.5 m³·mol⁻¹	ChemAxon
Polarizability	135.29 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C63H122O6

IUPAC name

1,3-bis(icosanoyloxy)propan-2-yl icosanoate

InChI Identifier

InChI=1S/C63H122O6/c1-4-7-10-13-16-19-22-25-28-31-34-37-40-43-46-49-52-55-61(64)67-58-60(69-63(66)57-54-51-48-45-42-39-36-33-30-27-24-21-18-15-12-9-6-3)59-68-62(65)56-53-50-47-44-41-38-35-32-29-26-23-20-17-14-11-8-5-2/h60H,4-59H2,1-3H3

InChI Key

KCVWRCXEUJUXIG-UHFFFAOYSA-N

Isomeric SMILES

[H]C(COC(=O)CCCCCCCCCCCCCCCCCCC)(COC(=O)CCCCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCC

Average Molecular Weight

975.6392

Monoisotopic Molecular Weight

974.924141636

Classification

Description

Belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Triradylcglycerols

Direct Parent

Triacylglycerols

Alternative Parents

Substituents

Triacyl-sn-glycerol
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Triacylglycerols (LMGL03010003 )

Ontology

Physiological effect

Health effect:

Health condition:

Metabolism and nutrition disorders:

Obesity

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Cell and elements:

Extracellular

Tissue and substructures:

Adipose tissue

Subcellular:

Biofluid and excreta:

Blood

Process

Naturally occurring process:

Biological process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Multicellular process:

Inflammatory response

Biochemical process:

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	C 77.56%; H 12.60%; O 9.84%	DFC
Melting Point	Mp 78°	DFC
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000009-f914314c4f99d5990e4e	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000000009-f914314c4f99d5990e4e	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03fr-0000009007-5f6aa2db8f900e909442	2017-10-04	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2020-06-30	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0000000009-992721c5c75cf5ec61e5	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0000000009-992721c5c75cf5ec61e5	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03fr-0010009007-52d2b3c1ac9903dfcbb5	2021-09-21	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0002-0000000009-57face8254241680bece	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-0000000009-57face8254241680bece	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0002-0000000009-57face8254241680bece	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-4210004029-92b7aceb4a643791153c	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0c01-9353007143-d5027f93c99e952b3b75	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006t-3249101100-76c56e5f56d6a245c7f9	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0229-0007007009-5963ec16f32d95e25ccf	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03dr-0009002000-131c78a60a8ca4a77bbe	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-08g0-1019001000-5fe1854470fb185e2278	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0000000009-d2ce2f663fce4243eff3	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0000000009-d2ce2f663fce4243eff3	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0159-0009009009-ce693f9116ff83f757ce	2021-09-25	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

455365

ChEMBL ID

Not Available

KEGG Compound ID

C00422

Pubchem Compound ID

522017

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB05414

CRC / DFC (Dictionary of Food Compounds) ID

BFQ89-A:BFQ89-A

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

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

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Name	Gene Name	UniProt ID
Carnitine O-palmitoyltransferase 1, muscle isoform	CPT1B	Q92523
Carnitine O-palmitoyltransferase 1, liver isoform	CPT1A	P50416
Carnitine O-palmitoyltransferase 2, mitochondrial	CPT2	P23786
Liver carboxylesterase 1	CES1	P23141
Pancreatic triacylglycerol lipase	PNLIP	P16233
Hepatic triacylglycerol lipase	LIPC	P11150
Lysosomal acid lipase/cholesteryl ester hydrolase	LIPA	P38571
Inactive pancreatic lipase-related protein 1	PNLIPRP1	P54315
Patatin-like phospholipase domain-containing protein 3	PNPLA3	Q9NST1
Gastric triacylglycerol lipase	LIPF	P07098
Endothelial lipase	LIPG	Q9Y5X9
Diacylglycerol O-acyltransferase 1	DGAT1	O75907
Pancreatic lipase-related protein 2	PNLIPRP2	P54317
Lipoprotein lipase	LPL	P06858
Monoglyceride lipase	MGLL	Q99685
Apolipoprotein A-I	APOA1	P02647
Apolipoprotein E	APOE	P02649
Apolipoprotein B-100	APOB	P04114
Protein disulfide-isomerase	P4HB	P07237
2-acylglycerol O-acyltransferase 2	MOGAT2	Q3SYC2
Patatin-like phospholipase domain-containing protein 4	PNPLA4	P41247
Diacylglycerol O-acyltransferase 2	DGAT2	Q96PD7
2-acylglycerol O-acyltransferase 1	MOGAT1	Q96PD6
2-acylglycerol O-acyltransferase 3	MOGAT3	Q86VF5
Glycerol-3-phosphate acyltransferase 3	AGPAT9	Q53EU6
Patatin-like phospholipase domain-containing protein 2	PNPLA2	Q96AD5
Pancreatic lipase-related protein 3	PNLIPRP3	Q17RR3