ChemFOnt: Showing chemical card for DG(16:1(9Z)/18:3(6Z,9Z,12Z)/0:0) (CFc000003182)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:48:13 UTC

Chemfont ID

CFc000003182

Molecule Identification

Common Name

DG(16:1(9Z)/18:3(6Z,9Z,12Z)/0:0)

Definition

DG(16:1(9Z)/18:3(6Z,9Z,12Z)/0:0) is a diglyceride, or a diacylglycerol (DAG). It is a glyceride consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Diacylglycerols can have many different combinations of fatty acids attached at both the C-1 and C-2 positions. DG(16:1(9Z)/18:3(6Z,9Z,12Z)/0:0), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of g-linolenic acid at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the g-linolenic acid moiety is derived from animal fats. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Dacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections. Synthesis of diacylglycerol begins with glycerol-3-phosphate, which is derived primarily from dihydroxyacetone phosphate, a product of glycolysis (usually in the cytoplasm of liver or adipose tissue cells). Glycerol-3-phosphate is first acylated with acyl-coenzyme A (acyl-CoA) to form lysophosphatidic acid, which is then acylated with another molecule of acyl-CoA to yield phosphatidic acid. Phosphatidic acid is then de-phosphorylated to form diacylglycerol.Diacylglycerols are precursors to triacylglycerols (triglyceride), which are formed by the addition of a third fatty acid to the diacylglycerol under the catalysis of diglyceride acyltransferase. Since diacylglycerols are synthesized via phosphatidic acid, they will usually contain a saturated fatty acid at the C-1 position on the glycerol moiety and an unsaturated fatty acid at the C-2 position.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₃₇H₆₄O₅

Average Molecular Weight

588.9011

Monoisotopic Molecular Weight

588.475375158

IUPAC Name

(2S)-1-(hexadec-9-enoyloxy)-3-hydroxypropan-2-yl octadeca-6,9,12-trienoate

Traditional Name

(2S)-1-(hexadec-9-enoyloxy)-3-hydroxypropan-2-yl octadeca-6,9,12-trienoate

CAS Registry Number

None

SMILES

[H][C@](CO)(COC(=O)CCCCCCCC=CCCCCCC)OC(=O)CCCCC=CCC=CCC=CCCCCC

InChI Identifier

InChI=1S/C37H64O5/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(40)42-35(33-38)34-41-36(39)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h11,13-14,16-18,22,24,35,38H,3-10,12,15,19-21,23,25-34H2,1-2H3/t35-/m0/s1

InChI Key

ALRUJMSZDYDUJX-DHUJRADRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
1,2-acyl-sn-glycerol
Diacylglycerol
Diradylglycerol
Fatty acid ester
Glycerolipid
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Carbonyl group
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Health effect

Metabolic disorder

Metabolic syndrome (PMID: 26273583)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 20671299)

Tissue

All Tissues (HMDB: HMDB0007133)

Cellular substructure

Membrane (HMDB: HMDB0007133)
Extracellular (HMDB: HMDB0007133)
Golgi apparatus membrane (PMID: 26153463)
Cell membrane (PMID: 26153463)

Organelle

Endoplasmic reticulum (PMID: 26153463)

Cell

All cells and tissues (HMDB: HMDB0007133)

Source

Exogenous

Exogenous (HMDB: HMDB0007133)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0007133)

Process

Naturally occurring process

Industrial application

Pharmaceutical industry

Biomarker

Insulin resistance ()

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	1.9e-05 g/L	ALOGPS
logP	9.39	ALOGPS
logP	11.44	ChemAxon
logS	-7.5	ALOGPS
pKa (Strongest Acidic)	14.58	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	32	ChemAxon
Refractivity	181.37 m³·mol⁻¹	ChemAxon
Polarizability	74.42 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB024327

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for DG(16:1(9Z)/18:3(6Z,9Z,12Z)/0:0) (CFc000003182)

MOL for CFc000003182 (DG(16:1(9Z)/18:3(6Z,9Z,12Z)/0:0))

3D MOL for CFc000003182 (DG(16:1(9Z)/18:3(6Z,9Z,12Z)/0:0))

3D SDF for CFc000003182 (DG(16:1(9Z)/18:3(6Z,9Z,12Z)/0:0))

3D-SDF for CFc000003182 (DG(16:1(9Z)/18:3(6Z,9Z,12Z)/0:0))

PDB for CFc000003182 (DG(16:1(9Z)/18:3(6Z,9Z,12Z)/0:0))

3D PDB for CFc000003182 (DG(16:1(9Z)/18:3(6Z,9Z,12Z)/0:0))

SMILES for CFc000003182 (DG(16:1(9Z)/18:3(6Z,9Z,12Z)/0:0))

INCHI for CFc000003182 (DG(16:1(9Z)/18:3(6Z,9Z,12Z)/0:0))

Structure for CFc000003182 (DG(16:1(9Z)/18:3(6Z,9Z,12Z)/0:0))

3D Structure for CFc000003182 (DG(16:1(9Z)/18:3(6Z,9Z,12Z)/0:0))