Record Information
Version3.6
Creation Date2008-09-12 01:13:01 UTC
Update Date2013-02-09 00:15:41 UTC
HMDB IDHMDB07011
Secondary Accession NumbersNone
Metabolite Identification
Common NameDG(14:0/16:0/0:0)
DescriptionDG(14:0/16:0/0:0) 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(14:0/16:0/0:0), in particular, consists of one chain of myristic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The myristic acid moiety is derived from nutmeg and butter, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. 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
Synonyms
  1. 1-Myristoyl-2-palmitoyl-sn-glycerol
  2. DAG(14:0/16:0)
  3. DAG(30:0)
  4. DG(14:0/16:0)
  5. DG(30:0)
  6. Diacylglycerol
  7. Diacylglycerol(14:0/16:0)
  8. Diacylglycerol(30:0)
  9. Diglyceride
Chemical FormulaC33H64O5
Average Molecular Weight540.8583
Monoisotopic Molecular Weight540.475375158
IUPAC Name(2S)-1-hydroxy-3-(tetradecanoyloxy)propan-2-yl hexadecanoate
Traditional IUPAC Name(2S)-1-hydroxy-3-(tetradecanoyloxy)propan-2-yl hexadecanoate
CAS Registry NumberNot Available
SMILES
[H][C@](CO)(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC
InChI Identifier
InChI=1S/C33H64O5/c1-3-5-7-9-11-13-15-16-18-20-22-24-26-28-33(36)38-31(29-34)30-37-32(35)27-25-23-21-19-17-14-12-10-8-6-4-2/h31,34H,3-30H2,1-2H3/t31-/m0/s1
InChI KeyNYNQTTOUQMCOEM-HKBQPEDESA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassGlycerolipids
Sub ClassDiacylglycerols
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Carboxylic Acid Ester
  • Dicarboxylic Acid Derivative
  • Fatty Acid Ester
  • Primary Alcohol
Direct ParentDiacylglycerols
Ontology
StatusDetected 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
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
water solubility2.180E-05 g/LALOGPS
logP9.59ALOGPS
logP11.11ChemAxon
logS-7.4ALOGPS
pKa (strongest acidic)14.58ChemAxon
pKa (strongest basic)-3ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count1ChemAxon
polar surface area72.83ChemAxon
rotatable bond count32ChemAxon
refractivity158.5ChemAxon
polarizability70.38ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location
  • All Tissues
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReference
BloodDetected and Quantified0.58 +/- 0.21 uMAdult (>18 years old)BothNormal
Abnormal Concentrations
Not Available
Predicted Concentrations Help
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0.707894354 +/- 0.313324307 uMAdult (>18 years old)BothNormal (Most Probable)Calculated using MetaboAnalyst
Blood4 +/- 1.670329309 uMAdult (>18 years old)BothNormal (Upper Limit)Calculated using MetaboAnalyst
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB024205
KNApSAcK IDNot Available
Chemspider ID24765845
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB07011
Metagene LinkHMDB07011
METLIN IDNot Available
PubChem Compound13734178
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Only showing the first 50 proteins. There are 130 proteins in total.

Enzymes

Gene Name:
DGKQ
Uniprot ID:
P52824
Gene Name:
PNLIP
Uniprot ID:
P16233
Gene Name:
DGKG
Uniprot ID:
P49619
Gene Name:
LIPC
Uniprot ID:
P11150
Gene Name:
PPAP2C
Uniprot ID:
O43688
Gene Name:
DGKA
Uniprot ID:
P23743
Gene Name:
DGKD
Uniprot ID:
Q16760
Gene Name:
DGKE
Uniprot ID:
P52429
Gene Name:
LIPF
Uniprot ID:
P07098
Gene Name:
PPAP2A
Uniprot ID:
O14494
Gene Name:
DGKB
Uniprot ID:
Q9Y6T7
Gene Name:
LIPG
Uniprot ID:
Q9Y5X9
Gene Name:
DGKI
Uniprot ID:
O75912
Gene Name:
CEL
Uniprot ID:
P19835
Gene Name:
PPAP2B
Uniprot ID:
O14495
Gene Name:
DGAT1
Uniprot ID:
O75907
Gene Name:
PNLIPRP2
Uniprot ID:
P54317
Gene Name:
DGKZ
Uniprot ID:
Q13574
Gene Name:
LPL
Uniprot ID:
P06858
Gene Name:
GAL3ST1
Uniprot ID:
Q99999
Gene Name:
LIPE
Uniprot ID:
Q05469
Gene Name:
CDS2
Uniprot ID:
O95674
Gene Name:
CDS1
Uniprot ID:
Q92903
Gene Name:
RAPGEF2
Uniprot ID:
Q9Y4G8
Gene Name:
PRKCA
Uniprot ID:
P17252
Gene Name:
CIT
Uniprot ID:
O14578
Gene Name:
PRKCB
Uniprot ID:
P05771
Gene Name:
PRKCZ
Uniprot ID:
Q05513
Gene Name:
PRKCI
Uniprot ID:
P41743
Gene Name:
ROCK1
Uniprot ID:
Q13464
Gene Name:
PRKD1
Uniprot ID:
Q15139
Gene Name:
PRKCG
Uniprot ID:
P05129
Gene Name:
ROCK2
Uniprot ID:
O75116
Gene Name:
PRKCD
Uniprot ID:
Q05655
Gene Name:
PRKD3
Uniprot ID:
O94806

Only showing the first 50 proteins. There are 130 proteins in total.