| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2008-09-11 19:15:13 -0600 |
| Update Date |
2013-02-08 17:16:03 -0700 |
| HMDB ID |
HMDB07142 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
DG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/0:0) |
| Description |
DG(16:1(9Z)/20:4(8Z,11Z,14Z,17Z)/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)/20:4(8Z,11Z,14Z,17Z)/0:0), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of eicsoatetraenoic acid at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the eicsoatetraenoic acid moiety is derived from fish oils. 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 |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
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| Synonyms |
- 1-Palmitoleoyl-2-eicsoate
- 1-Palmitoleoyl-2-eicsoatetraenoyl-sn-glycerol
- 1-Palmitoleoyl-2-eicsoic acid
- DAG(16:1/20:4)
- DAG(16:1n7/20:4n3)
- DAG(16:1w7/20:4w3)
- DAG(36:5)
- DG(16:1/20:4)
- DG(16:1n7/20:4n3)
- DG(16:1w7/20:4w3)
- DG(36:5)
- Diacylglycerol
- Diacylglycerol(16:1/20:4)
- Diacylglycerol(16:1n7/20:4n3)
- Diacylglycerol(16:1w7/20:4w3)
- Diacylglycerol(36:5)
- Diglyceride
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| Chemical Formula |
C39H66O5 |
| Average Molecular Weight |
614.9383 |
| Monoisotopic Molecular Weight |
614.491025222 |
| IUPAC Name |
(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoate |
| Traditional IUPAC Name |
(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoate |
| CAS Registry Number |
Not Available |
| SMILES |
[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCC\C=C/C\C=C/C\C=C/C\C=C/CC |
| InChI Identifier |
InChI=1S/C39H66O5/c1-3-5-7-9-11-13-15-17-18-19-20-22-24-26-28-30-32-34-39(42)44-37(35-40)36-43-38(41)33-31-29-27-25-23-21-16-14-12-10-8-6-4-2/h5,7,11,13-14,16-18,20,22,37,40H,3-4,6,8-10,12,15,19,21,23-36H2,1-2H3/b7-5-,13-11-,16-14-,18-17-,22-20-/t37-/m0/s1 |
| InChI Key |
CMBHKSKRJUUOQH-YGFCVJAISA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Lipids |
| Class |
Glycerolipids |
| Sub Class |
Diacylglycerols |
| Other Descriptors |
- Aliphatic Acyclic Compounds
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| Substituents |
- Acyclic Alkene
- Carboxylic Acid Ester
- Dicarboxylic Acid Derivative
- Fatty Acid Ester
- Hydroxyeicosapolyenoic Acid
- Primary Alcohol
- Saccharide
- Triose Monosaccharide
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| Direct Parent |
Diacylglycerols |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
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| Biofunction |
- Cell signaling
- Energy source
- Fuel and energy storage
- Fuel or energy source
- Membrane component
- Membrane integrity/stability
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| Application |
- Nutrients
- Stabilizers
- Surfactants and Emulsifiers
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| Cellular locations |
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| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
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| Predicted Properties |
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| Spectra |
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Not Available
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| Biological Properties |
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| Cellular Locations |
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| Biofluid Locations |
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| Tissue Location |
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| Pathways |
Not Available
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| Normal Concentrations |
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| Blood |
Detected and Quantified |
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0.961 +/- 0.023 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
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| Abnormal Concentrations |
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Not Available |
| Associated Disorders and Diseases |
|---|
| Disease References |
None |
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB024336 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
24765946  |
| KEGG Compound ID |
Not Available |
| BioCyc ID |
Not Available |
| BiGG ID |
Not Available |
| Wikipedia Link |
Not Available |
| NuGOwiki Link |
HMDB07142 |
| Metagene Link |
HMDB07142 |
| METLIN ID |
Not Available |
| PubChem Compound |
53478041 |
| PDB ID |
Not Available |
| ChEBI ID |
Not Available |
| References |
|---|
| Synthesis Reference |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available
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| General References |
Not Available
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| Enzymes |
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| Name: |
Endothelial lipase
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| Reactions: |
- triacylglycerol + H2O = diacylglycerol + a carboxylate [RN:R01369]
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| Gene Name: |
LIPG |
| Uniprot ID: |
Q9Y5X9 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Lipoprotein lipase
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| Reactions: |
- triacylglycerol + H2O = diacylglycerol + a carboxylate [RN:R01369]
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| Gene Name: |
LPL |
| Uniprot ID: |
P06858 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Galactosylceramide sulfotransferase
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| Reactions: |
- 3'-phosphoadenylyl sulfate + a galactosylceramide = adenosine 3',5'-bisphosphate + a galactosylceramidesulfate [RN:R04017 R06279]
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| Gene Name: |
GAL3ST1 |
| Uniprot ID: |
Q99999 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Hormone-sensitive lipase
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| Reactions: |
- (1) diacylglycerol + H2O = monoacylglycerol + a carboxylate [RN:R05209]
- (2) triacylglycerol + H2O = diacylglycerol + a carboxylate [RN:R01369]
- (3) monoacylglycerol + H2O = glycerol + a carboxylate [RN:R07293]
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| Gene Name: |
LIPE |
| Uniprot ID: |
Q05469 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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| Name: |
Diacylglycerol kinase eta
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| Reactions: |
- ATP + 1,2-diacyl-sn-glycerol = ADP + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02240]
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| Gene Name: |
DGKH |
| Uniprot ID: |
Q86XP1 |
| Protein Sequence: |
FASTA |
| Gene Sequence: |
FASTA |
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