Human Metabolome Database Version 3.5

Showing metabocard for DG(14:0/18:1(9Z)/0:0) (HMDB07015)

Record Information
Version 3.5
Creation Date 2008-09-11 19:13:05 -0600
Update Date 2013-02-08 17:15:42 -0700
HMDB ID HMDB07015
Secondary Accession Numbers None
Metabolite Identification
Common Name DG(14:0/18:1(9Z)/0:0)
Description DG(14:0/18:1(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(14:0/18:1(9Z)/0:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of oleic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the oleic acid moiety is 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 Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-Myristoyl-2-oleoyl-sn-glycerol
  2. DAG(14:0/18:1)
  3. DAG(14:0/18:1n9)
  4. DAG(14:0/18:1w9)
  5. DAG(32:1)
  6. DG(14:0/18:1)
  7. DG(14:0/18:1n9)
  8. DG(14:0/18:1w9)
  9. DG(32:1)
  10. Diacylglycerol
  11. Diacylglycerol(14:0/18:1)
  12. Diacylglycerol(14:0/18:1n9)
  13. Diacylglycerol(14:0/18:1w9)
  14. Diacylglycerol(32:1)
  15. Diglyceride
Chemical Formula C35H66O5
Average Molecular Weight 566.8955
Monoisotopic Molecular Weight 566.491025222
IUPAC Name (2S)-1-hydroxy-3-(tetradecanoyloxy)propan-2-yl (9Z)-octadec-9-enoate
Traditional IUPAC Name (2S)-1-hydroxy-3-(tetradecanoyloxy)propan-2-yl (9Z)-octadec-9-enoate
CAS Registry Number Not Available
SMILES [H][C@](CO)(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier InChI=1S/C35H66O5/c1-3-5-7-9-11-13-15-16-17-18-20-22-24-26-28-30-35(38)40-33(31-36)32-39-34(37)29-27-25-23-21-19-14-12-10-8-6-4-2/h16-17,33,36H,3-15,18-32H2,1-2H3/b17-16-/t33-/m0/s1
InChI Key XEQQGHISHUGMIP-ASUORMEESA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Glycerolipids
Sub Class Diacylglycerols
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Acyclic Alkene
  • Carboxylic Acid Ester
  • Dicarboxylic Acid Derivative
  • Fatty Acid Ester
  • Primary Alcohol
Direct Parent Diacylglycerols
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Energy source
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 1.960E-05 g/L ALOGPS
LogP 9.82 ALOGPS
LogP 11.64 ChemAxon
LogS -7.46 ALOGPS
pKa (strongest acidic) 14.58 ChemAxon
pKa (strongest basic) -3 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 72.83 A2 ChemAxon
Rotatable Bond Count 33 ChemAxon
Refractivity 168.82 ChemAxon
Polarizability 73.46 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • All Tissues
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
1.07 +/- 0.14 uM Adult (>18 years old) Both Normal
Abnormal Concentrations
Not Available
Predicted Concentrations Help
Biofluid Value Original age Original sex Original condition Comments
Blood 0.634214353 +/- 0.169264232 uM Adult (>18 years old) Both Normal (Most Probable) Calculated using MetaboAnalyst
Blood 4 +/- 1.670329309 uM Adult (>18 years old) Both Normal (Upper Limit) Calculated using MetaboAnalyst
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB024209
KNApSAcK ID Not Available
Chemspider ID 24765849 Link_out
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB07015 Link_out
Metagene Link HMDB07015 Link_out
METLIN ID Not Available
PubChem Compound 14275341 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes

Show all enzymes and transporters Important Only showing the first 50 enzymes. There are 130 enzymes in total.

Name: Diacylglycerol kinase theta
Reactions: Not Available
Gene Name: DGKQ
Uniprot ID: P52824 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pancreatic triacylglycerol lipase
Reactions: Not Available
Gene Name: PNLIP
Uniprot ID: P16233 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-1
Reactions: Not Available
Gene Name: PLCB1
Uniprot ID: Q9NQ66 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-4
Reactions: Not Available
Gene Name: PLCB4
Uniprot ID: Q15147 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-2
Reactions: Not Available
Gene Name: PLCB2
Uniprot ID: Q00722 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase gamma
Reactions: Not Available
Gene Name: DGKG
Uniprot ID: P49619 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hepatic triacylglycerol lipase
Reactions: Not Available
Gene Name: LIPC
Uniprot ID: P11150 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase beta-3
Reactions: Not Available
Gene Name: PLCB3
Uniprot ID: Q01970 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Inactive pancreatic lipase-related protein 1
Reactions: Not Available
Gene Name: PNLIPRP1
Uniprot ID: P54315 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-2
Reactions: Not Available
Gene Name: PLCG2
Uniprot ID: P16885 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipid phosphate phosphohydrolase 2
Reactions: Not Available
Gene Name: PPAP2C
Uniprot ID: O43688 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Patatin-like phospholipase domain-containing protein 3
Reactions: Not Available
Gene Name: PNPLA3
Uniprot ID: Q9NST1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase alpha
Reactions: Not Available
Gene Name: DGKA
Uniprot ID: P23743 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase delta
Reactions: Not Available
Gene Name: DGKD
Uniprot ID: Q16760 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase epsilon
Reactions: Not Available
Gene Name: DGKE
Uniprot ID: P52429 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Gastric triacylglycerol lipase
Reactions: Not Available
Gene Name: LIPF
Uniprot ID: P07098 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipid phosphate phosphohydrolase 1
Reactions: Not Available
Gene Name: PPAP2A
Uniprot ID: O14494 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase beta
Reactions: Not Available
Gene Name: DGKB
Uniprot ID: Q9Y6T7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Endothelial lipase
Reactions: Not Available
Gene Name: LIPG
Uniprot ID: Q9Y5X9 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase iota
Reactions: Not Available
Gene Name: DGKI
Uniprot ID: O75912 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Bile salt-activated lipase
Reactions: Not Available
Gene Name: CEL
Uniprot ID: P19835 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipid phosphate phosphohydrolase 3
Reactions: Not Available
Gene Name: PPAP2B
Uniprot ID: O14495 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol O-acyltransferase 1
Reactions: Not Available
Gene Name: DGAT1
Uniprot ID: O75907 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase gamma-1
Reactions: Not Available
Gene Name: PLCG1
Uniprot ID: P19174 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pancreatic lipase-related protein 2
Reactions: Not Available
Gene Name: PNLIPRP2
Uniprot ID: P54317 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase zeta
Reactions: Not Available
Gene Name: DGKZ
Uniprot ID: Q13574 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-phosphatidylinositol 4,5-bisphosphate phosphodiesterase delta-1
Reactions: Not Available
Gene Name: PLCD1
Uniprot ID: P51178 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipoprotein lipase
Reactions: Not Available
Gene Name: LPL
Uniprot ID: P06858 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Galactosylceramide sulfotransferase
Reactions: Not Available
Gene Name: GAL3ST1
Uniprot ID: Q99999 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hormone-sensitive lipase
Reactions: Not Available
Gene Name: LIPE
Uniprot ID: Q05469 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidate cytidylyltransferase 2
Reactions: Not Available
Gene Name: CDS2
Uniprot ID: O95674 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Choline-phosphate cytidylyltransferase A
Reactions: Not Available
Gene Name: PCYT1A
Uniprot ID: P49585 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidate cytidylyltransferase 1
Reactions: Not Available
Gene Name: CDS1
Uniprot ID: Q92903 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylcholine:ceramide cholinephosphotransferase 2
Reactions: Not Available
Gene Name: SGMS2
Uniprot ID: Q8NHU3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: CDP-diacylglycerol--inositol 3-phosphatidyltransferase
Reactions: Not Available
Gene Name: CDIPT
Uniprot ID: O14735 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylcholine:ceramide cholinephosphotransferase 1
Reactions: Not Available
Gene Name: SGMS1
Uniprot ID: Q86VZ5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Rap guanine nucleotide exchange factor 2
Reactions: Not Available
Gene Name: RAPGEF2
Uniprot ID: Q9Y4G8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: RAF proto-oncogene serine/threonine-protein kinase
Reactions: Not Available
Gene Name: RAF1
Uniprot ID: P04049 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein kinase C alpha type
Reactions: Not Available
Gene Name: PRKCA
Uniprot ID: P17252 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Serine/threonine-protein kinase A-Raf
Reactions: Not Available
Gene Name: ARAF
Uniprot ID: P10398 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Citron Rho-interacting kinase
Reactions: Not Available
Gene Name: CIT
Uniprot ID: O14578 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein kinase C beta type
Reactions: Not Available
Gene Name: PRKCB
Uniprot ID: P05771 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein kinase C zeta type
Reactions: Not Available
Gene Name: PRKCZ
Uniprot ID: Q05513 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein kinase C iota type
Reactions: Not Available
Gene Name: PRKCI
Uniprot ID: P41743 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Rho-associated protein kinase 1
Reactions: Not Available
Gene Name: ROCK1
Uniprot ID: Q13464 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Serine/threonine-protein kinase D1
Reactions: Not Available
Gene Name: PRKD1
Uniprot ID: Q15139 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein kinase C gamma type
Reactions: Not Available
Gene Name: PRKCG
Uniprot ID: P05129 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Rho-associated protein kinase 2
Reactions: Not Available
Gene Name: ROCK2
Uniprot ID: O75116 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein kinase C delta type
Reactions: Not Available
Gene Name: PRKCD
Uniprot ID: Q05655 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Serine/threonine-protein kinase D3
Reactions: Not Available
Gene Name: PRKD3
Uniprot ID: O94806 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA