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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2008-09-12 01:15:30 UTC
Update Date2022-03-07 02:49:38 UTC
HMDB IDHMDB0007158
Secondary Accession Numbers
  • HMDB07158
Metabolite Identification
Common NameDG(18:0/18:0/0:0)
DescriptionDG(18:0/18:0/0:0) 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(18:0/18:0/0:0), in particular, consists of two chains of stearic acid at the C-1 and C-2 positions. The stearic acid moieties are derived from animal fats, coco butter and sesame 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?1582752435
Synonyms
ValueSource
(-)-(S)-Glycerin-1,2-distearatHMDB
(2S)-1,2-Bis-O-stearylglycerolHMDB
(2S)-3-Hydroxypropane-1,2-diyl distearoateHMDB
(S)-(-)-1,2-Distearoyl-sn-glycerolHMDB
(S)-1,2-DioctadecanoylglycerolHMDB
(S)-1,2-DistearoylglycerolHMDB
(S)-2,3-Bis-stearoyloxy-propan-1-olHMDB
1,2-Di-O-stearoyl-sn-glycerolHMDB
1,2-Distearoyl-sn-glycerolHMDB
Diacyl glycerolHMDB
(2S)-3-Hydroxypropane-1,2-diyl distearoic acidHMDB
DAG(36:0)HMDB
DAG(18:0/18:0)HMDB
Diacylglycerol(36:0)HMDB
Diacylglycerol(18:0/18:0)HMDB
DiglycerideHMDB
DG(18:0/18:0)HMDB
1,2-Distearoyl-rac-glycerolHMDB
DiacylglycerolHMDB
1,2-Dioctadecanoyl-rac-glycerolHMDB
DG(36:0)HMDB
DG(18:0/18:0/0:0)Lipid Annotator
Chemical FormulaC39H76O5
Average Molecular Weight625.0177
Monoisotopic Molecular Weight624.569275542
IUPAC Name(2S)-1-hydroxy-3-(octadecanoyloxy)propan-2-yl octadecanoate
Traditional Namediacyl glycerol
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C39H76O5/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/h37,40H,3-36H2,1-2H3/t37-/m0/s1
InChI KeyUHUSDOQQWJGJQS-QNGWXLTQSA-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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.7e-05 g/LALOGPS
logP10.36ALOGPS
logP13.78ChemAxon
logS-7.6ALOGPS
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
Refractivity186.1 m³·mol⁻¹ChemAxon
Polarizability83.2 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+257.50231661259
DarkChem[M-H]-248.53231661259
DeepCCS[M+H]+253.67130932474
DeepCCS[M-H]-251.31330932474
DeepCCS[M-2H]-285.31630932474
DeepCCS[M+Na]+260.54330932474
AllCCS[M+H]+275.932859911
AllCCS[M+H-H2O]+275.532859911
AllCCS[M+NH4]+276.232859911
AllCCS[M+Na]+276.332859911
AllCCS[M-H]-257.632859911
AllCCS[M+Na-2H]-261.432859911
AllCCS[M+HCOO]-265.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DG(18:0/18:0/0:0)[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC3801.9Standard polar33892256
DG(18:0/18:0/0:0)[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC3797.8Standard non polar33892256
DG(18:0/18:0/0:0)[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCC4476.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
DG(18:0/18:0/0:0),1TMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)OC[C@H](CO[Si](C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC4325.1Semi standard non polar33892256
DG(18:0/18:0/0:0),1TBDMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)OC[C@H](CO[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCCCCCC4652.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - DG(18:0/18:0/0:0) GC-MS (1 TMS) - 70eV, Positivesplash10-03dr-5151956000-f3cfe411b34b1c221b642017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DG(18:0/18:0/0:0) GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-16Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DG(18:0/18:0/0:0) GC-MS ("DG(18:0/18:0/0:0),1TMS,#1" TMS) - 70eV, PositiveNot Available2021-11-02Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - DG(18:0/18:0/0:0) Orbitrap 22V, positive-QTOFsplash10-0a4i-0000009000-8e2b49808d5e3ba8021b2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DG(18:0/18:0/0:0) Orbitrap 29V, positive-QTOFsplash10-0a4i-7440009000-7ae5fe88175fdeb6fb5f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DG(18:0/18:0/0:0) Orbitrap 37V, positive-QTOFsplash10-0a5a-9310001000-85fce82520a3cc11397a2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DG(18:0/18:0/0:0) Orbitrap 52V, positive-QTOFsplash10-0ac1-9100000000-a1f2263667fdc881e94c2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - DG(18:0/18:0/0:0) Orbitrap 59V, positive-QTOFsplash10-0ac1-9100000000-3d9ba6996495929e12f12020-07-22HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(18:0/18:0/0:0) 10V, Positive-QTOFsplash10-0006-0000009000-b7a4da88d31b5bcc2c452017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(18:0/18:0/0:0) 20V, Positive-QTOFsplash10-052f-0009009000-1ba3fc9d6773d912e0ef2017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(18:0/18:0/0:0) 40V, Positive-QTOFsplash10-0006-0009009000-e19946aa33b3b6470f092017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(18:0/18:0/0:0) 10V, Positive-QTOFsplash10-05r3-1049008000-49dcad482d1f6cdbdb6c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(18:0/18:0/0:0) 20V, Positive-QTOFsplash10-066u-3197102000-2f093b5f0a07bfed3cb42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(18:0/18:0/0:0) 40V, Positive-QTOFsplash10-0693-9373000000-93a030c229e94346a6e12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(18:0/18:0/0:0) 10V, Negative-QTOFsplash10-00e9-1054009000-050434164c58cd42a01a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(18:0/18:0/0:0) 20V, Negative-QTOFsplash10-001i-2095001000-85b9d03fc704e33c4ca12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(18:0/18:0/0:0) 40V, Negative-QTOFsplash10-00lr-1091000000-17b8d9f52bf6076415d62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(18:0/18:0/0:0) 10V, Positive-QTOFsplash10-0006-0000009000-4f85695573a777cd0fb72021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(18:0/18:0/0:0) 20V, Positive-QTOFsplash10-052f-0008009000-7bc5dee7fe55e1f720472021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(18:0/18:0/0:0) 40V, Positive-QTOFsplash10-0006-0008009000-0348034e2d9f82dbea4a2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(18:0/18:0/0:0) 10V, Positive-QTOFsplash10-0002-0000009000-0c5603e78a419f79d9c22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(18:0/18:0/0:0) 20V, Positive-QTOFsplash10-0002-0000009000-0c5603e78a419f79d9c22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(18:0/18:0/0:0) 40V, Positive-QTOFsplash10-03di-0009001000-1fc1ebe517eccab43dab2021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.69 +/- 0.19 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.900 +/- 0.144 uMAdult (>18 years old)BothNormal (Most Probable)Calculated using MetaboAnalyst
Blood4.567 +/- 0.401 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 IDFDB024352
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543705
PDB IDNot Available
ChEBI ID41847
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 10 proteins. There are 133 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

Transporters

General function:
Lipid transport and metabolism
Specific function:
Involved in translocation of long-chain fatty acids (LFCA) across the plasma membrane. The LFCA import appears to be hormone-regulated in a tissue-specific manner. In adipocytes, but not myocytes, insulin induces a rapid translocation of FATP1 from intracellular compartments to the plasma membrane, paralleled by increased LFCA uptake. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane- associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LFCA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism. Has acyl-CoA ligase activity for long-chain and very-long-chain fatty acids
Gene Name:
SLC27A1
Uniprot ID:
Q6PCB7
Molecular weight:
71107.5

Only showing the first 10 proteins. There are 133 proteins in total.