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DG(16:0/16:0/0:0) (YMDB01127)

Identification
YMDB IDYMDB01127
NameDG(16:0/16:0/0:0)
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionDG(16:0/16:0/0:0) 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(16:0/16:0/0:0) is also a substrate of diacylglycerol kinase. It is involved in the phospholipid metabolic pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • (+)-D-Dipalmitin
  • 1,2-dipalmitoyl-rac-glycerol
  • DAG(16:0/16:0)
  • DAG(32:0)
  • DG(16:0/16:0)
  • DG(32:0)
  • di-O-acylglycerols
  • Diacylglycerol
  • Diacylglycerol(16:0/16:0)
  • Diacylglycerol(32:0)
  • diacylglycerols
  • Diglyceride
  • diglycerides
  • Hexadecanoic acid, 1-(hydroxymethyl)-1,2-ethanediyl ester
  • Palmitin, 1,2-di-
  • (S)-1-(Hydroxymethyl)ethane-1,2-diyl dipalmitate
  • 1,2-Dihexadecanoyl-sn-glycerol
  • (S)-1-(Hydroxymethyl)ethane-1,2-diyl dipalmitic acid
  • 1,2-Dihexadecanoyl-rac-glycerol
  • DG(16:0/16:0/0:0)
CAS number30334-71-5
WeightAverage: 568.9114
Monoisotopic: 568.506675286
InChI KeyJEJLGIQLPYYGEE-MGBGTMOVSA-N
InChIInChI=1S/C35H68O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(37)39-32-33(31-36)40-35(38)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33,36H,3-32H2,1-2H3/t33-/m1/s1
IUPAC Name(2S)-1-(hexadecanoyloxy)-3-hydroxypropan-2-yl hexadecanoate
Traditional IUPAC Namediacylglycerol
Chemical FormulaC35H68O5
SMILES[H][C@@](CO)(COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC
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
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility2.0e-05 g/LALOGPS
logP9.91ALOGPS
logP12ChemAxon
logS-7.5ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count34ChemAxon
Refractivity167.7 m³·mol⁻¹ChemAxon
Polarizability75.44 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • lipid particle
  • endoplasmic reticulum
  • nucleus
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
Choline metabolismPW002494 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycerophospholipid metabolismPW002493 ThumbThumb?image type=greyscaleThumb?image type=simple
Lysolipid incorporation into ER PC(16:0/16:0)PW002784 ThumbThumb?image type=greyscaleThumb?image type=simple
Triacylglycerol metabolismPW002695 ThumbThumb?image type=greyscaleThumb?image type=simple
Triacylglycerol metabolism TG(16:0/16:0/16:0)PW007758 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycerophospholipid metabolismec00564 Map00564
SMPDB Reactions
PA(16:0/0:0) + Palmityl-CoA → DG(16:0/16:0/0:0) + Coenzyme A
DG(16:0/16:0/0:0) + hydron + Cytidine triphosphate → CDP-DG(16:0/16:0) + Pyrophosphate
Citicoline + DG(16:0/16:0/0:0) → PC(16:0/16:0) + Cytidine monophosphate + hydron
DG(16:0/16:0/0:0) + CDP-Ethanolamine → Cytidine monophosphate + hydron + PE(16:0/16:0)
PA(16:0/16:0) + water → DG(16:0/16:0/0:0) + phosphate
KEGG Reactions
CDP-Ethanolamine + DG(16:0/16:0/0:0) ↔ PE(14:0/16:1(9Z)) + Cytidine monophosphate + hydron
Citicoline + DG(16:0/16:0/0:0) → phosphatidylcholine + Cytidine monophosphate
acyl-CoA + DG(16:0/16:0/0:0) ↔ hydron + TG(18:0/18:0/18:0) + Coenzyme A
LPA(16:0/0:0) + water ↔ DG(16:0/16:0/0:0) + phosphate + hydron
PE(14:0/16:1(9Z)) + 6-O-{alpha-D-mannosyl-(1->2)-alpha-D-mannosyl-(1->6)-2-O-[(2-aminoethyl)phosphoryl]-alpha-D-mannosyl-(1->4)-alpha-D-glucosaminyl}-O-acyl-1-phosphatidyl-1D-myo-inositol ↔ DG(16:0/16:0/0:0) + 6-[6-(2-aminoethylphosphoryl)-alpha-mannosyl-(1->6)-2-(2-aminoethylphosphoryl)-alpha-mannosyl-(1->6)-alpha-2-(2-aminoethylphosphoryl)mannosyl-(1->4)-alpha-glucosaminyl]-O-acyl-1-phosphatidyl-1D-myo-inositol
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
12500 ± 50 umol/L SD media with 2% raffinose37 oCBY4741PMID: 19174513
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Ejsing, C. S., Sampaio, J. L., Surendranath, V., Duchoslav, E., Ekroos, K., Klemm, R. W., Simons, K., Shevchenko, A. (2009). "Global analysis of the yeast lipidome by quantitative shotgun mass spectrometry." Proc Natl Acad Sci U S A 106:2136-2141.19174513
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID18035
HMDB IDHMDB07098
Pubchem Compound ID99931
Kegg IDC00165
ChemSpider ID559127
FOODB IDFDB024292
Wikipedia IDNot Available
BioCyc IDDIACYLGLYCEROL

Enzymes

Protein Details
1. Diacylglycerol O-acyltransferase 1
General function:
Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:
Catalyzes the terminal and only committed step in triacylglycerol synthesis by using diacylglycerol and fatty acyl CoA as substrates. Required for storage lipid synthesis. May be involved in lipid particle synthesis from the endoplasmic reticulum and ergosterol biosynthesis
Gene Name:
DGA1
Uniprot ID:
Q08650
Molecular weight:
47710.89844
Reactions
Acyl-CoA + 1,2-diacylglycerol → CoA + triacylglycerol.
Protein Details
2. Probable 1-acyl-sn-glycerol-3-phosphate acyltransferase
General function:
Involved in acyltransferase activity
Specific function:
May be an acyltransferase with an altered substrate specificity that enables it to use a C-26-CoA in place of the C-16 or C-18-CoAs used by the wild-type protein
Gene Name:
SLC1
Uniprot ID:
P33333
Molecular weight:
33886.69922
Reactions
Acyl-CoA + 1-acyl-sn-glycerol 3-phosphate → CoA + 1,2-diacyl-sn-glycerol 3-phosphate.
Protein Details
3. Lysophospholipid acyltransferase
General function:
Involved in 1-acylglycerol-3-phosphate O-acyltransferas
Specific function:
Membrane-bound O-acyltransferase that mediates the incorporation of unsaturated acyl chains into the sn-2 position of phopholipids. Preferentially acylates lysophosphocholine, but also lysophosphoethanolamine and lysophosphatidylglycerol
Gene Name:
ALE1
Uniprot ID:
Q08548
Molecular weight:
72227.39844
Reactions
Acyl-CoA + 1-acyl-sn-glycerol 3-phosphate → CoA + 1,2-diacyl-sn-glycerol 3-phosphate.
Acyl-CoA + 1-acyl-sn-glycero-3-phosphocholine → CoA + 1,2-diacyl-sn-glycero-3-phosphocholine.
Acyl-CoA + 1-acyl-sn-glycero-3-phosphoethanolamine → CoA + 1,2-diacyl-sn-glycero-3-phosphoethanolamine.
Protein Details
4. CTP-dependent diacylglycerol kinase 1
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
Involved in pre-tRNA splicing. CTP- dependent diacylglycerol kinase that catalyzes the phosphorylation of diacylglycerol (DAG) to phosphatidate (PA). Controls phosphatidate levels at the nuclear envelope. Counteracts the activity of PAH1/SMP2. Involved in the resistance to nickel chloride and nalidixic acid. May be involved in vesicle trafficking between the endoplasmic reticulum and the Golgi apparatus
Gene Name:
DGK1
Uniprot ID:
Q12382
Molecular weight:
32839.80078
Reactions
CTP + 1,2-diacyl-sn-glycerol → CDP + 1,2-diacyl-sn-glycerol 3-phosphate.
Protein Details
5. Cholinephosphotransferase 1
General function:
Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:
Involved in protein-dependent process of phospholipid transport to distribute phosphatidyl choline to the lumenal surface. The multiple transmembrane domains and lumenal hydrophilic domains of the cholinephosphotransferase might participate in the transport process
Gene Name:
CPT1
Uniprot ID:
P17898
Molecular weight:
44829.0
Reactions
CDP-choline + 1,2-diacylglycerol → CMP + a phosphatidylcholine.
Protein Details
6. Phosphatidate cytidylyltransferase
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
Supplies CDP-diacylglycerol, which may play an important role as both a precursor to phosphoinositide biosynthesis in the plasma membrane and as a negative effector of phosphatidylinositol 4-kinase activity, thereby exerting an effect on cell proliferation via a lipid-dependent signal transduction cascade
Gene Name:
CDS1
Uniprot ID:
P38221
Molecular weight:
51822.39844
Reactions
CTP + phosphatidate → diphosphate + CDP-diacylglycerol.
Protein Details
7. Sterol esterase TGL1
General function:
Involved in lipid metabolic process
Specific function:
Mediates the hydrolysis of steryl esters. Required for mobilization of steryl ester, thereby playing a central role in lipid metabolism. May have weak lipase activity toward triglycerides upon some conditions, however, the relevance of such activity is unclear in vivo
Gene Name:
TGL1
Uniprot ID:
P34163
Molecular weight:
62978.39844
Reactions
A steryl ester + H(2)O → a sterol + a fatty acid.
Protein Details
8. Lipase 2
General function:
Involved in hydrolase activity, acting on ester bonds
Specific function:
Lipolytic activity towards triacylglycerols and diacylglycerols with short-chain fatty acids
Gene Name:
TGL2
Uniprot ID:
P54857
Molecular weight:
37499.89844
Reactions
Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.
Protein Details
9. Lipase 3
General function:
Involved in metabolic process
Specific function:
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process
Gene Name:
TGL3
Uniprot ID:
P40308
Molecular weight:
73611.79688
Reactions
Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.
Protein Details
10. Lipase 5
General function:
Involved in metabolic process
Specific function:
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process. May have a specific role in sporulation
Gene Name:
TGL5
Uniprot ID:
Q12043
Molecular weight:
84715.10156
Reactions
Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.
Protein Details
11. Lipase 4
General function:
Involved in metabolic process
Specific function:
Releases specific fatty acids from neutral lipid triacylglycerols (TAG) thereby supplying fatty acids to a general acylation process. May have a specific role in sporulation
Gene Name:
TGL4
Uniprot ID:
P36165
Molecular weight:
102716.0
Reactions
Triacylglycerol + H(2)O → diacylglycerol + a carboxylate.
Protein Details
12. Phosphatidic acid phosphohydrolase 1
General function:
vacuole fusion, non-autophagic
Specific function:
Mg(2+)-dependent phosphatidate (PA) phosphatase which catalyzes the dephosphorylation of PA to yield diacylglycerol. Required for de novo lipid synthesis and formation of lipid droplets. Controles transcription of phospholipid biosynthetic genes and nuclear structure by regulating the amount of membrane present at the nuclear envelope. Involved in plasmid maintenance, in respiration and in cell proliferation.
Gene Name:
PAH1
Uniprot ID:
P32567
Molecular weight:
95029.985
Reactions
Protein Details
13. Phosphatidate cytidylyltransferase, mitochondrial
General function:
CDP-diacylglycerol biosynthetic process
Specific function:
Catalyzes the formation of CDP-diacylglycerol (CDP-DAG) from phosphatidic acid (PA) in the mitochondrial inner membrane. Required for the biosynthesis of the dimeric phospholipid cardiolipin, which stabilizes supercomplexes of the mitochondrial respiratory chain in the mitochondrial inner membrane.
Gene Name:
TAM41
Uniprot ID:
P53230
Molecular weight:
44199.33
Reactions
Protein Details
14. Lysophosphatidic acid:oleoyl-CoA acyltransferase 1
General function:
lipid particle organization
Specific function:
Acyl-CoA-dependent lysophosphatidic acid acyltransferase with preference for oleoyl-CoA. Involved in triacylglyceride homeostasis and lipid droplet formation. Involved in vacuolar protein sorting.
Gene Name:
LOA1
Uniprot ID:
Q06508
Molecular weight:
33815.635
Reactions