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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-12 01:16:30 UTC
Update Date2020-02-26 21:27:21 UTC
HMDB IDHMDB0007218
Secondary Accession Numbers
  • HMDB07218
Metabolite Identification
Common NameDG(18:1(9Z)/18:1(9Z)/0:0)
DescriptionDG(18:1(9Z)/18:1(9Z)/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(18:1(9Z)/18:1(9Z)/0:0), in particular, consists of two chains of oleic acid at the C-1 and C-2 positions. The oleic acid moieties are derived from vegetable oils, especially olive and canola oil. 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
Data?1582752441
Synonyms
ValueSource
1,2-Di-(9Z-octadecenoyl)-sn-glycerolChEBI
DG(18:1/18:1/0:0)ChEBI
sn-1,2-DioleinChEBI
sn-1,2-DioleoylglycerolChEBI
1,2-Dioleoyl-rac-glycerolHMDB
Di-oleoylglycerolHMDB
Glycerol dioleateHMDB
DioleinHMDB
DioleoylglycerolHMDB
1,2-DioleoylglycerolHMDB
Diacylglycerol(36:2)HMDB
DG(18:1/18:1)HMDB
DG(36:2)HMDB
DAG(36:2)HMDB
DiglycerideHMDB
Diacylglycerol(18:1/18:1)HMDB
DiacylglycerolHMDB
DAG(18:1/18:1)HMDB
1,2-Di(9Z-octadecenoyl)-rac-glycerolHMDB
DG(18:1(9Z)/18:1(9Z)/0:0)Lipid Annotator
(+--)-1,2-DioleoylglycerolMeSH
1,2-DioleinMeSH
9-Octadecenoic acid (9Z)-, 1-(hydroxymethyl)-1,2-ethanediyl esterMeSH
Glyceryl 1,2-dioleateMeSH
9-Octadecenoic acid (Z)-, 1-(hydroxymethyl)-1,2-ethanediyl esterMeSH
1,2-Glyceryl dioleateMeSH
(+--)-1,2-DioleinMeSH
1,2-Dioleoyl-DL-glycerolMeSH
9-Octadecenoic acid (9Z)-, 1,1'-(1-(hydroxymethyl)-1,2-ethanediyl) esterMeSH
9-Octadecenoic acid (9Z)-, diester with 1,2,3-propanetriolMeSH
Oleic acid diglycerideMeSH
Chemical FormulaC39H72O5
Average Molecular Weight620.986
Monoisotopic Molecular Weight620.537975414
IUPAC Name(2S)-1-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propan-2-yl (9Z)-octadec-9-enoate
Traditional Name1,2-dioleoyl-sn-glycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C39H72O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,37,40H,3-16,21-36H2,1-2H3/b19-17-,20-18-/t37-/m0/s1
InChI KeyAFSHUZFNMVJNKX-LLWMBOQKSA-N
Chemical Taxonomy
Description 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 Solubility1.2e-05 g/LALOGPS
logP10.26ALOGPS
logP13.06ChemAxon
logS-7.7ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity188.34 m³·mol⁻¹ChemAxon
Polarizability80.99 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03dr-4351956000-02493870893e9eaf8021Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 43V, positivesplash10-0ufr-0025089000-86867947e5d654a1367eSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 43V, positivesplash10-014i-0092020000-48754474f83689f7da27Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 43V, positivesplash10-03dr-0009000000-38a71500caac14fe5e10Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-00di-0001009000-ad8aa7c4c14b2b4811f0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 22V, positivesplash10-0079-0079007000-878059044a8b6bd25bbfSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 29V, positivesplash10-00kr-1389001000-88d226dc029ad1418f08Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 38V, positivesplash10-00ks-6965000000-0b86ba8ef5ef1cff8b10Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 45V, positivesplash10-00lj-8931000000-8dca4ecba590c00ca67eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 53V, positivesplash10-00l2-9600000000-310135ebf19be0cf22fcSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 60V, positivesplash10-05o1-9500000000-c6cc9222e27414e1a8c3Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 68V, positivesplash10-05o1-9300000000-fbca81be56d5e04c9706Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 76V, positivesplash10-015a-9200000000-19fd61863fddb281d45eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 91V, positivesplash10-067i-9100000000-d08d8fd7ca1191a0774fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 115V, positivesplash10-067i-9000000000-b9daf31db2718f97206bSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 137V, positivesplash10-0690-9000000000-22a10438f123ad9c81c2Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 168V, positivesplash10-0690-9000000000-78e32b4bdcdd00b25bd7Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 199V, positivesplash10-0ar0-9000000000-6c348586c0b4d81be070Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 245V, positivesplash10-0ar0-9000000000-1e4a43dab5d1cc87b20aSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 43V, positivesplash10-0udr-0026069000-1d883e799bc5f0d1e2e1Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 43V, positivesplash10-014j-0970000000-3b55de48b23381fee738Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 43V, positivesplash10-00ds-0900000000-4e9641ccd9863ab49ac2Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 43V, positivesplash10-0002-3940000000-f7ed9cc10bd7a4729a0fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-9185b686832caa4f55c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0009009000-33724f4f211af0262245Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0009009000-36758b4e03b2a3c426eaSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
Tissue Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified4.06 +/- 0.54 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedNewborn (0-30 days old)Not Specified
Premature neonates
details
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood2.666 +/- 0.998 uMAdult (>18 years old)BothNormal (Most Probable)Calculated using MetaboAnalyst
Blood7.783 +/- 1.455 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
FooDB IDFDB094043
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543716
PDB IDNot Available
ChEBI ID52333
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 10 proteins. There are 131 proteins in total.

Enzymes

General function:
Involved in diacylglycerol kinase activity
Specific function:
Phosphorylates diacylglycerol (DAG) to generate phosphatidic acid (PA). May regulate the activity of protein kinase C by controlling the balance between these two signaling lipids. Activated in the nucleus in response to alpha-thrombin and nerve growth factor. May be involved in cAMP- induced activation of NR5A1 and subsequent steroidogenic gene transcription by delivering PA as ligand for NR5A1. Acts synergistically with NR5A1 on CYP17 transcriptional activity
Gene Name:
DGKQ
Uniprot ID:
P52824
Molecular weight:
101154.0
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
PNLIP
Uniprot ID:
P16233
Molecular weight:
51156.48
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.
Gene Name:
PLCB1
Uniprot ID:
Q9NQ66
Molecular weight:
138565.805
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 form has a role in retina signal transduction.
Gene Name:
PLCB4
Uniprot ID:
Q15147
Molecular weight:
136105.065
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.
Gene Name:
PLCB2
Uniprot ID:
Q00722
Molecular weight:
134023.21
General function:
Involved in diacylglycerol kinase activity
Specific function:
Reverses the normal flow of glycerolipid biosynthesis by phosphorylating diacylglycerol back to phosphatidic acid
Gene Name:
DGKG
Uniprot ID:
P49619
Molecular weight:
89095.3
General function:
Involved in catalytic activity
Specific function:
Hepatic lipase has the capacity to catalyze hydrolysis of phospholipids, mono-, di-, and triglycerides, and acyl-CoA thioesters. It is an important enzyme in HDL metabolism. Hepatic lipase binds heparin.
Gene Name:
LIPC
Uniprot ID:
P11150
Molecular weight:
55914.1
General function:
Involved in lipid metabolic process
Specific function:
Crucial for the intracellular hydrolysis of cholesteryl esters and triglycerides that have been internalized via receptor-mediated endocytosis of lipoprotein particles. Important in mediating the effect of LDL (low density lipoprotein) uptake on suppression of hydroxymethylglutaryl-CoA reductase and activation of endogenous cellular cholesteryl ester formation.
Gene Name:
LIPA
Uniprot ID:
P38571
Molecular weight:
45418.71
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.
Gene Name:
PLCB3
Uniprot ID:
Q01970
Molecular weight:
138797.725
General function:
Involved in catalytic activity
Specific function:
May function as inhibitor of dietary triglyceride digestion. Lacks detectable lipase activity towards triglycerides, diglycerides, phosphatidylcholine, galactolipids or cholesterol esters (in vitro) (By similarity).
Gene Name:
PNLIPRP1
Uniprot ID:
P54315
Molecular weight:
Not Available

Only showing the first 10 proteins. There are 131 proteins in total.