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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-12 01:15:16 UTC
Update Date2017-12-23 07:50:07 UTC
HMDB IDHMDB0007145
Secondary Accession Numbers
  • HMDB07145
Metabolite Identification
Common NameDG(16:1(9Z)/22:1(13Z)/0:0)
DescriptionDG(16:1(9Z)/22:1(13Z)/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)/22:1(13Z)/0:0), in particular, consists of one chain of palmitoleic acid at the C-1 position and one chain of erucic acid at the C-2 position. The palmitoleic acid moiety is derived from animal fats and vegetable oils, while the erucic acid moiety is derived from seed oils and avocados. 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
Thumb
Synonyms
ValueSource
1-(9Z-hexadecenoyl)-2-(13Z-docosenoyl)-sn-glycerol; DG(16:1(9Z)/22:1(13Z)/0:0)Lipid Annotator
DAG(38:2)Lipid Annotator
DAG(16:1/22:1)Lipid Annotator
Diacylglycerol(38:2)Lipid Annotator
Diacylglycerol(16:1/22:1)Lipid Annotator
DiglycerideLipid Annotator
DG(38:2)Lipid Annotator
DiacylglycerolLipid Annotator
DG(16:1/22:1)Lipid Annotator
1-palmitoleoyl-2-erucoyl-sn-glycerolLipid Annotator
1-(9Z-hexadecenoyl)-2-(13Z-docosenoyl)-sn-glycerolLipid Annotator
DG(16:1(9Z)/22:1(13Z)/0:0)Lipid Annotator
Chemical FormulaC41H76O5
Average Molecular Weight649.0391
Monoisotopic Molecular Weight648.569275542
IUPAC Name(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (13Z)-docos-13-enoate
Traditional Name(2S)-1-[(9Z)-hexadec-9-enoyloxy]-3-hydroxypropan-2-yl (13Z)-docos-13-enoate
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C41H76O5/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-24-26-28-30-32-34-36-41(44)46-39(37-42)38-45-40(43)35-33-31-29-27-25-23-16-14-12-10-8-6-4-2/h14,16-18,39,42H,3-13,15,19-38H2,1-2H3/b16-14-,18-17-/t39-/m0/s1
InChI KeyBRTWZKUDSRQGQH-NFIJARSKSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassDiradylglycerols
Direct Parent1,2-diacylglycerols
Alternative Parents
Substituents
  • 1,2-acyl-sn-glycerol
  • Fatty acid ester
  • Fatty acyl
  • Dicarboxylic acid or derivatives
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.1e-05 g/LALOGPS
logP10.47ALOGPS
logP13.95ChemAxon
logS-7.8ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count38ChemAxon
Refractivity197.54 m³·mol⁻¹ChemAxon
Polarizability85.03 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0000009000-9cb3686d663a4e72a34aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01pk-0009004000-fcc9ca35a4e0bb19350eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0292-0009004000-afe26d341aef3249b226View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue Location
  • All Tissues
Pathways
NameSMPDB/PathwhizKEGG
De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/18:3(9Z,12Z,15Z))ThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/18:4(6Z,9Z,12Z,15Z))ThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/20:1(11Z))ThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/20:2(11Z,14Z))ThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
De Novo Triacylglycerol Biosynthesis TG(16:1(9Z)/22:1(13Z)/20:3(5Z,8Z,11Z))ThumbThumb?image type=greyscaleThumb?image type=simpleNot Available
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.022 +/- 0.010 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.007644615 +/- 0.004258609 uMAdult (>18 years old)BothNormal (Most Probable)Calculated using MetaboAnalyst
Blood0.566666667 +/- 0.351188458 uMAdult (>18 years old)BothNormal (Upper Limit)Calculated using MetaboAnalyst
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543780
PDB IDNot Available
ChEBI ID88483
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 10 proteins. There are 130 proteins in total.

Enzymes

General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Catalyzes the biosynthesis of phosphatidylinositol (PtdIns) as well as PtdIns:inositol exchange reaction. May thus act to reduce an excessive cellular PtdIns content. The exchange activity is due to the reverse reaction of PtdIns synthase and is dependent on CMP, which is tightly bound to the enzyme.
Gene Name:
CDIPT
Uniprot ID:
O14735
Molecular weight:
23538.47
General function:
Involved in calcium ion binding
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes. This phospholipase activity is very sensitive to calcium. May be important for formation and maintenance of the neuronal network in the postnatal brain (By similarity).
Gene Name:
PLCH2
Uniprot ID:
O75038
Molecular weight:
154666.975
General function:
Involved in diacylglycerol kinase activity
Specific function:
ATP + 1,2-diacylglycerol = ADP + 1,2-diacyl- sn-glycerol 3-phosphate
Gene Name:
DGKI
Uniprot ID:
O75912
Molecular weight:
116996.2
General function:
Involved in intracellular signaling pathway
Specific function:
Converts transient diacylglycerol (DAG) signals into prolonged physiological effects, downstream of PKC. Involved in resistance to oxidative stress
Gene Name:
PRKD3
Uniprot ID:
O94806
Molecular weight:
100469.8
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
Provides CDP-diacylglycerol an important precursor for the synthesis of phosphatidylinositol, phosphatidylglycerol, and cardiolipin.
Gene Name:
CDS2
Uniprot ID:
O95674
Molecular weight:
51417.5
General function:
Involved in protein serine/threonine kinase activity
Specific function:
PKC is activated by diacylglycerol which in turn phosphorylates a range of cellular proteins. PKC also serves as the receptor for phorbol esters, a class of tumor promoters
Gene Name:
PRKCG
Uniprot ID:
P05129
Molecular weight:
78447.2
General function:
Involved in protein serine/threonine kinase activity
Specific function:
Calcium-activated and phospholipid-dependent serine/threonine-protein kinase involved in various processes such as regulation of the B-cell receptor (BCR) signalosome, apoptosis and transcription regulation. Plays a key role in B-cell activation and function by regulating BCR-induced NF-kappa-B activation and B-cell suvival. Required for recruitment and activation of the IKK kinase to lipid rafts and mediates phosphorylation of CARD11/CARMA1 at 'Ser-559', 'Ser-644' and 'Ser- 652', leading to activate the NF-kappa-B signaling. Involved in apoptosis following oxidative damage:in case of oxidative conditions, specifically phosphorylates 'Ser-36' of isoform p66Shc of SHC1, leading to mitochondrial accumulation of p66Shc, where p66Shc acts as a reactive oxygen species producer. Acts as a coactivator of androgen receptor (ANDR)-dependent transcription, by being recruited to ANDR target genes and specifically mediating phosphorylation of 'Thr-6' of histone H3 (H3T6ph), a specific tag for epigenetic transcriptional activation that prevents demethylation of histone H3 'Lys-4' (H3K4me) by LSD1/KDM1A. Also involved in triglyceride homeostasis. Serves as the receptor for phorbol esters, a class of tumor promoters
Gene Name:
PRKCB
Uniprot ID:
P05771
Molecular weight:
76868.4
General function:
Involved in phosphoinositide phospholipase C activity
Specific function:
The production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) is mediated by activated phosphatidylinositol-specific phospholipase C enzymes. It is a crucial enzyme in transmembrane signaling.
Gene Name:
PLCG2
Uniprot ID:
P16885
Molecular weight:
147868.67
General function:
Involved in protein serine/threonine kinase activity
Specific function:
PKC is activated by diacylglycerol which in turn phosphorylates a range of cellular proteins. PKC also serves as the receptor for phorbol esters, a class of tumor promoters
Gene Name:
PRKCA
Uniprot ID:
P17252
Molecular weight:
76763.5
General function:
Involved in calcium ion binding
Specific function:
Mediates the production of the second messenger molecules diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3). Plays an important role in the regulation of intracellular signaling cascades. Becomes activated in response to ligand-mediated activation of receptor-type tyrosine kinases, such as PDGFRA, PDGFRB, FGFR1, FGFR2, FGFR3 and FGFR4. Plays a role in actin reorganization and cell migration.
Gene Name:
PLCG1
Uniprot ID:
P19174
Molecular weight:
148658.92

Only showing the first 10 proteins. There are 130 proteins in total.