Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-05-19 05:52:48 UTC
Update Date2022-11-30 19:16:35 UTC
HMDB IDHMDB0094305
Secondary Accession Numbers
  • HMDB94305
Metabolite Identification
Common NameDG(a-21:0/i-16:0/0:0)
DescriptionDG(a-21:0/i-16:0/0:0) belongs to the family of Diacylglycerols. These are glycerolipids lipids containing a common glycerol backbone to which at least one fatty acyl group is esterified. DG(a-21:0/i-16:0/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway.
Structure
Data?1563871177
Synonyms
ValueSource
1-anteisoheneicosanoyl-2-isohexadecanoyl-sn-glycerolSMPDB, HMDB
DG(a-21:0/i-16:0)SMPDB, HMDB
DG(37:0)SMPDB, HMDB
Dag(a-21:0/i-16:0)SMPDB, HMDB
Dag(37:0)SMPDB, HMDB
Diacylglycerol(a-21:0/i-16:0)SMPDB, HMDB
Diacylglycerol(37:0)SMPDB, HMDB
DiacylglycerolSMPDB, HMDB
DiglycerideSMPDB, HMDB
DG(a-21:0/i-16:0/0:0)SMPDB
(2S)-3-Hydroxy-2-[(14-methylpentadecanoyl)oxy]propyl 18-methylicosanoic acidGenerator, HMDB
Chemical FormulaC40H78O5
Average Molecular Weight639.059
Monoisotopic Molecular Weight638.584925612
IUPAC Name(2S)-3-hydroxy-2-[(14-methylpentadecanoyl)oxy]propyl 18-methylicosanoate
Traditional Name(2S)-3-hydroxy-2-[(14-methylpentadecanoyl)oxy]propyl 18-methylicosanoate
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCCCC(C)CC)OC(=O)CCCCCCCCCCCCC(C)C
InChI Identifier
InChI=1S/C40H78O5/c1-5-37(4)31-27-23-19-15-10-8-6-7-9-11-16-20-24-28-32-39(42)44-35-38(34-41)45-40(43)33-29-25-21-17-13-12-14-18-22-26-30-36(2)3/h36-38,41H,5-35H2,1-4H3/t37?,38-/m0/s1
InChI KeyJXVGFOPPYFCZLK-OALPUDEUSA-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 DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
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
logP10.27ALOGPS
logP13.91ChemAxon
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 Count37ChemAxon
Refractivity190.6 m³·mol⁻¹ChemAxon
Polarizability84.92 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]+255.49331661259
DarkChem[M-H]-244.49331661259
DeepCCS[M+H]+261.29130932474
DeepCCS[M-H]-258.93330932474
DeepCCS[M-2H]-292.81330932474
DeepCCS[M+Na]+268.04130932474
AllCCS[M+H]+272.732859911
AllCCS[M+H-H2O]+272.332859911
AllCCS[M+NH4]+273.132859911
AllCCS[M+Na]+273.232859911
AllCCS[M-H]-257.232859911
AllCCS[M+Na-2H]-262.932859911
AllCCS[M+HCOO]-269.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
DG(a-21:0/i-16:0/0:0)[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCCCC(C)CC)OC(=O)CCCCCCCCCCCCC(C)C3791.6Standard polar33892256
DG(a-21:0/i-16:0/0:0)[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCCCC(C)CC)OC(=O)CCCCCCCCCCCCC(C)C3968.6Standard non polar33892256
DG(a-21:0/i-16:0/0:0)[H][C@](CO)(COC(=O)CCCCCCCCCCCCCCCCC(C)CC)OC(=O)CCCCCCCCCCCCC(C)C4465.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
DG(a-21:0/i-16:0/0:0),1TMS,isomer #1CCC(C)CCCCCCCCCCCCCCCCC(=O)OC[C@H](CO[Si](C)(C)C)OC(=O)CCCCCCCCCCCCC(C)C4456.0Semi standard non polar33892256
DG(a-21:0/i-16:0/0:0),1TBDMS,isomer #1CCC(C)CCCCCCCCCCCCCCCCC(=O)OC[C@H](CO[Si](C)(C)C(C)(C)C)OC(=O)CCCCCCCCCCCCC(C)C4704.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - DG(a-21:0/i-16:0/0:0) GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DG(a-21:0/i-16:0/0:0) GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-17Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - DG(a-21:0/i-16:0/0:0) GC-MS ("DG(a-21:0/i-16:0/0:0),1TMS,#1" TMS) - 70eV, PositiveNot Available2021-11-02Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(a-21:0/i-16:0/0:0) 10V, Positive-QTOFsplash10-0a4i-0000009000-f73e04973450fc7176422017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(a-21:0/i-16:0/0:0) 20V, Positive-QTOFsplash10-03lr-0009004000-347a9e1fde31a89c3db72017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(a-21:0/i-16:0/0:0) 40V, Positive-QTOFsplash10-08h9-0009004000-25327065f7f33b086f752017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(a-21:0/i-16:0/0:0) 10V, Negative-QTOFsplash10-052r-2079008000-1c944e99a586cba500212021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(a-21:0/i-16:0/0:0) 20V, Negative-QTOFsplash10-05dr-3069000000-705b9e539f16109825882021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(a-21:0/i-16:0/0:0) 40V, Negative-QTOFsplash10-0a6r-2169000000-1e223e031a7e75bcb8ec2021-09-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(a-21:0/i-16:0/0:0) 10V, Positive-QTOFsplash10-0a4i-0000009000-21fd620f481b3cfc210a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(a-21:0/i-16:0/0:0) 20V, Positive-QTOFsplash10-03lr-0009004000-0cae5382d6041ff4a6292021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(a-21:0/i-16:0/0:0) 40V, Positive-QTOFsplash10-08h9-0009004000-7a57befa0ab6ec3c100b2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(a-21:0/i-16:0/0:0) 10V, Positive-QTOFsplash10-03di-0000009000-823c70d734c3fc93caff2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(a-21:0/i-16:0/0:0) 20V, Positive-QTOFsplash10-03di-0000009000-823c70d734c3fc93caff2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(a-21:0/i-16:0/0:0) 40V, Positive-QTOFsplash10-0a50-0019701000-950955ff46ec62eb47dd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(a-21:0/i-16:0/0:0) 10V, Positive-QTOFsplash10-000i-3297007000-3ed251445efd3281d7712021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(a-21:0/i-16:0/0:0) 20V, Positive-QTOFsplash10-0a4s-9355001000-2fb1786b5046815b11902021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - DG(a-21:0/i-16:0/0:0) 40V, Positive-QTOFsplash10-0a4r-9412000000-11f81f72e655306b79ab2021-09-25Wishart 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 IDFDB066261
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound131802733
PDB IDNot Available
ChEBI IDNot Available
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. Quehenberger O, Armando AM, Brown AH, Milne SB, Myers DS, Merrill AH, Bandyopadhyay S, Jones KN, Kelly S, Shaner RL, Sullards CM, Wang E, Murphy RC, Barkley RM, Leiker TJ, Raetz CR, Guan Z, Laird GM, Six DA, Russell DW, McDonald JG, Subramaniam S, Fahy E, Dennis EA: Lipidomics reveals a remarkable diversity of lipids in human plasma. J Lipid Res. 2010 Nov;51(11):3299-305. doi: 10.1194/jlr.M009449. Epub 2010 Jul 29. [PubMed:20671299 ]
  2. Lopez-Lopez A, Lopez-Sabater MC, Campoy-Folgoso C, Rivero-Urgell M, Castellote-Bargallo AI: Fatty acid and sn-2 fatty acid composition in human milk from Granada (Spain) and in infant formulas. Eur J Clin Nutr. 2002 Dec;56(12):1242-54. [PubMed:12494309 ]
  3. Jenkins B, West JA, Koulman A: A review of odd-chain fatty acid metabolism and the role of pentadecanoic Acid (c15:0) and heptadecanoic Acid (c17:0) in health and disease. Molecules. 2015 Jan 30;20(2):2425-44. doi: 10.3390/molecules20022425. [PubMed:25647578 ]
  4. Kingsbury KJ, Morgan DM: The analysis of the fatty acids of normal human depot fat by gas-liquid chromatography. Biochem J. 1964 Jan;90(1):140-7. [PubMed:5832283 ]

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.