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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-09 07:57:39 UTC
Update Date2022-11-30 19:26:35 UTC
HMDB IDHMDB0116368
Secondary Accession NumbersNone
Metabolite Identification
Common NameDG(8:0/8:0/0:0)
DescriptionDiglycerides (DGs) are also known as diacylglycerols or diacylglycerides, meaning that they are glycerides consisting of two fatty acid chains covalently bonded to a glycerol molecule through ester linkages. DG(8:0/8:0/0:0), in particular, consists of one chain of caprylic acid at the C-1 position and one chain of caprylic acid at the C-2 position. Mono- and diacylglycerols are common food additives used to blend together certain ingredients, such as oil and water, which would not otherwise blend well. Diacylglycerols are often found in bakery products, beverages, ice cream, chewing gum, shortening, whipped toppings, margarine, and confections.
Structure
Data?1563873708
Synonyms
ValueSource
1,2-Dicapryloyl-sn-glycerolChEBI
1,2-DioctanoylglycerolChEBI
1,2-Octanoyl-sn-diglycerideChEBI
D-alpha,beta-DicaprylinChEBI
DicaprylglycerideChEBI
Octanoic acid, 1-(hydroxymethyl)-1,2-ethanediyl esterChEBI
sn-1,2-DicaprilinChEBI
sn-1,2-DioctanoylglycerolChEBI
D-a,b-DicaprylinGenerator
D-Α,β-dicaprylinGenerator
Octanoate, 1-(hydroxymethyl)-1,2-ethanediyl esterGenerator
1,2-Dioctanoylglycerol, (S)-isomerMeSH
1,2-DicapryloylglycerolMeSH
DiC8MeSH
1,2-Dioctanoyl-rac-glycerolMeSH
1-capryloyl-2-capryloyl-sn-glycerol SMPDB, HMDB
DG(16:0) SMPDB, HMDB
Dag(8:0/8:0/0:0) SMPDB, HMDB
Dag(16:0) SMPDB, HMDB
Diacylglycerol(8:0/8:0/0:0) SMPDB, HMDB
Diacylglycerol(16:0) SMPDB, HMDB
Diacylglycerol SMPDB, HMDB
DiglycerideSMPDB, HMDB
DG(8:0/8:0/0:0)SMPDB, ChEBI
1,2-dicapryloyl-rac-glycerolLipid Annotator, HMDB
DG(16:0)Lipid Annotator
Diacylglycerol(8:0/8:0)Lipid Annotator, HMDB
DAG(8:0/8:0)Lipid Annotator, HMDB
DG(8:0/8:0)Lipid Annotator, HMDB
DAG(16:0)Lipid Annotator
DiacylglycerolLipid Annotator
Diacylglycerol(16:0)Lipid Annotator
1,2-Dioctanoyl-sn-glycerolMeSH
Chemical FormulaC19H36O5
Average Molecular Weight344.492
Monoisotopic Molecular Weight344.256274259
IUPAC Name(2S)-1-hydroxy-3-(octanoyloxy)propan-2-yl octanoate
Traditional Name(2S)-1-hydroxy-3-(octanoyloxy)propan-2-yl octanoate
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCC)OC(=O)CCCCCCC
InChI Identifier
InChI=1S/C19H36O5/c1-3-5-7-9-11-13-18(21)23-16-17(15-20)24-19(22)14-12-10-8-6-4-2/h17,20H,3-16H2,1-2H3/t17-/m0/s1
InChI KeyZQBULZYTDGUSSK-KRWDZBQOSA-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 effectNot Available
DispositionNot Available
Process
Naturally occurring process
RoleNot 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
logP5.18ALOGPS
logP4.89ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity94.08 m³·mol⁻¹ChemAxon
Polarizability40.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+188.4531661259
DarkChem[M-H]-184.93931661259
DeepCCS[M+H]+182.30530932474
DeepCCS[M-H]-179.94730932474
DeepCCS[M-2H]-213.90130932474
DeepCCS[M+Na]+189.12830932474
AllCCS[M+H]+191.932859911
AllCCS[M+H-H2O]+189.732859911
AllCCS[M+NH4]+194.032859911
AllCCS[M+Na]+194.532859911
AllCCS[M-H]-187.732859911
AllCCS[M+Na-2H]-188.932859911
AllCCS[M+HCOO]-190.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DG(8:0/8:0/0:0)[H][C@](CO)(COC(=O)CCCCCCC)OC(=O)CCCCCCC3350.4Standard polar33892256
DG(8:0/8:0/0:0)[H][C@](CO)(COC(=O)CCCCCCC)OC(=O)CCCCCCC2324.8Standard non polar33892256
DG(8:0/8:0/0:0)[H][C@](CO)(COC(=O)CCCCCCC)OC(=O)CCCCCCC2410.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
DG(8:0/8:0/0:0),1TMS,isomer #1CCCCCCCC(=O)OC[C@H](CO[Si](C)(C)C)OC(=O)CCCCCCC2425.2Semi standard non polar33892256
DG(8:0/8:0/0:0),1TBDMS,isomer #1CCCCCCCC(=O)OC[C@H](CO[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCC2678.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - DG(8:0/8:0/0:0) GC-MS (1 TMS) - 70eV, Positivesplash10-00fr-9443000000-6cf9dc38a892ce328a252017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DG(8:0/8:0/0:0) GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(8:0/8:0/0:0) 10V, Positive-QTOFsplash10-0ufs-1797000000-3c48af1aa6ec30406efd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(8:0/8:0/0:0) 20V, Positive-QTOFsplash10-004i-4930000000-5d4803070fa75a6f9e452021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(8:0/8:0/0:0) 40V, Positive-QTOFsplash10-056s-9600000000-d7a0684744bdcbc4c6e92021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(8:0/8:0/0:0) 10V, Positive-QTOFsplash10-03di-0009000000-88368969d80893c66c082021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(8:0/8:0/0:0) 20V, Positive-QTOFsplash10-0ufr-0089000000-781d7837a416f6bc151e2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(8:0/8:0/0:0) 40V, Positive-QTOFsplash10-0w29-0089000000-51e2807c05c5021562aa2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(8:0/8:0/0:0) 10V, Negative-QTOFsplash10-0006-4958000000-a08c241fae3d53aacbe82021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(8:0/8:0/0:0) 20V, Negative-QTOFsplash10-002f-2910000000-a6cc1398a59875ed0b3e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(8:0/8:0/0:0) 40V, Negative-QTOFsplash10-004l-0900000000-c25a9172bacc185222902021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(8:0/8:0/0:0) 10V, Positive-QTOFsplash10-014i-0009000000-76d98eb990a817d33ecb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(8:0/8:0/0:0) 20V, Positive-QTOFsplash10-014i-0009000000-76d98eb990a817d33ecb2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(8:0/8:0/0:0) 40V, Positive-QTOFsplash10-00di-0191000000-18621b03bf222137bb6d2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-13470
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound148879
PDB IDNot Available
ChEBI ID76979
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 References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. [PubMed:9034165 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Only showing the first 10 proteins. There are 132 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 132 proteins in total.