Showing metabocard for DG(18:1(9Z)/18:1(9Z)/0:0) (BMDB0007218)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 23:32:56 UTC
Update Date2020-06-04 20:21:04 UTC
MCDB ID BMDB0007218
Secondary Accession Numbers
  • BMDB07218
Metabolite Identification
Common NameDG(18:1(9Z)/18:1(9Z)/0:0)
DescriptionDG(18:1(9Z)/18:1(9Z)/0:0), also known as sn-1,2-dioleoylglycerol or sn-1,2-diolein, belongs to the class of organic compounds known as 1,2-diacylglycerols. These are diacylglycerols containing a glycerol acylated at positions 1 and 2. Thus, DG(18:1(9Z)/18:1(9Z)/0:0) is considered to be a diradylglycerol lipid molecule. DG(18:1(9Z)/18:1(9Z)/0:0) is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. DG(18:1(9Z)/18:1(9Z)/0:0) exists in all living organisms, ranging from bacteria to humans. DG(18:1(9Z)/18:1(9Z)/0:0) participates in a number of enzymatic reactions, within cattle. In particular, CDP-Ethanolamine and DG(18:1(9Z)/18:1(9Z)/0:0) can be converted into cytidine monophosphate and PE(18:1(9Z)/18:1(9Z)) through its interaction with the enzyme choline/ethanolaminephosphotransferase. In addition, CDP-Choline and DG(18:1(9Z)/18:1(9Z)/0:0) can be converted into cytidine monophosphate and PC(18:1(9Z)/18:1(9Z)) through its interaction with the enzyme choline/ethanolaminephosphotransferase. In cattle, DG(18:1(9Z)/18:1(9Z)/0:0) is involved in the metabolic pathway called phosphatidylcholine biosynthesis PC(18:1(9Z)/18:1(9Z)) pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Di-(9Z-octadecenoyl)-sn-glycerolChEBI
DG(18:1/18:1/0:0)ChEBI
sn-1,2-DioleinChEBI
sn-1,2-DioleoylglycerolChEBI
1,2-Dioleoyl-rac-glycerolHMDB
Di-oleoylglycerolHMDB
Glycerol dioleateHMDB
DioleinHMDB
DioleoylglycerolHMDB
1,2-DioleoylglycerolHMDB
Diacylglycerol(36:2)HMDB
DG(18:1/18:1)HMDB
DG(36:2)HMDB
DAG(36:2)HMDB
DiglycerideHMDB
Diacylglycerol(18:1/18:1)HMDB
DiacylglycerolHMDB
DAG(18:1/18:1)HMDB
1,2-Di(9Z-octadecenoyl)-rac-glycerolHMDB
(+--)-1,2-DioleoylglycerolHMDB
1,2-DioleinHMDB
9-Octadecenoic acid (9Z)-, 1-(hydroxymethyl)-1,2-ethanediyl esterHMDB
Glyceryl 1,2-dioleateHMDB
9-Octadecenoic acid (Z)-, 1-(hydroxymethyl)-1,2-ethanediyl esterHMDB
1,2-Glyceryl dioleateHMDB
(+--)-1,2-DioleinHMDB
1,2-Dioleoyl-DL-glycerolHMDB
9-Octadecenoic acid (9Z)-, 1,1'-(1-(hydroxymethyl)-1,2-ethanediyl) esterHMDB
9-Octadecenoic acid (9Z)-, diester with 1,2,3-propanetriolHMDB
Oleic acid diglycerideHMDB
DG(18:1(9Z)/18:1(9Z)/0:0)Lipid Annotator
Chemical FormulaC39H72O5
Average Molecular Weight620.986
Monoisotopic Molecular Weight620.537975414
IUPAC Name(2S)-1-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propan-2-yl (9Z)-octadec-9-enoate
Traditional Name1,2-dioleoyl-sn-glycerol
CAS Registry Number24529-88-2
SMILES
[H][C@](CO)(COC(=O)CCCCCCC\C=C/CCCCCCCC)OC(=O)CCCCCCC\C=C/CCCCCCCC
InChI Identifier
InChI=1S/C39H72O5/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(41)43-36-37(35-40)44-39(42)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h17-20,37,40H,3-16,21-36H2,1-2H3/b19-17-,20-18-/t37-/m0/s1
InChI KeyAFSHUZFNMVJNKX-LLWMBOQKSA-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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP10.26ALOGPS
logP13.06ChemAxon
logS-7.7ALOGPS
pKa (Strongest Acidic)14.58ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area72.83 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity188.34 m³·mol⁻¹ChemAxon
Polarizability80.99 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03dr-4351956000-02493870893e9eaf80212017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-10-16View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("DG(18:1(9Z)/18:1(9Z)/0:0),1TMS,#1" TMS) - 70eV, PositiveNot Available2021-11-02View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 43V, positivesplash10-0ufr-0025089000-86867947e5d654a1367e2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 43V, positivesplash10-014i-0092020000-48754474f83689f7da272020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 43V, positivesplash10-03dr-0009000000-38a71500caac14fe5e102020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-00di-0001009000-ad8aa7c4c14b2b4811f02020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 22V, positivesplash10-0079-0079007000-878059044a8b6bd25bbf2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 29V, positivesplash10-00kr-1389001000-88d226dc029ad1418f082020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 38V, positivesplash10-00ks-6965000000-0b86ba8ef5ef1cff8b102020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 45V, positivesplash10-00lj-8931000000-8dca4ecba590c00ca67e2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 53V, positivesplash10-00l2-9600000000-310135ebf19be0cf22fc2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 60V, positivesplash10-05o1-9500000000-c6cc9222e27414e1a8c32020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 68V, positivesplash10-05o1-9300000000-fbca81be56d5e04c97062020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 76V, positivesplash10-015a-9200000000-19fd61863fddb281d45e2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 91V, positivesplash10-067i-9100000000-d08d8fd7ca1191a0774f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 115V, positivesplash10-067i-9000000000-b9daf31db2718f97206b2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 137V, positivesplash10-0690-9000000000-22a10438f123ad9c81c22020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 168V, positivesplash10-0690-9000000000-78e32b4bdcdd00b25bd72020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 199V, positivesplash10-0ar0-9000000000-6c348586c0b4d81be0702020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 245V, positivesplash10-0ar0-9000000000-1e4a43dab5d1cc87b20a2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 43V, positivesplash10-0udr-0026069000-1d883e799bc5f0d1e2e12020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 43V, positivesplash10-014j-0970000000-3b55de48b23381fee7382020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 43V, positivesplash10-00ds-0900000000-4e9641ccd9863ab49ac22020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 43V, positivesplash10-0002-3940000000-f7ed9cc10bd7a4729a0f2020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000009000-9185b686832caa4f55c42017-10-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f79-0009009000-33724f4f211af02622452017-10-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0009009000-36758b4e03b2a3c426ea2017-10-04View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified25 +/- 2 uM details
Detected and Quantified55 +/- 4 uM details
Detected and Quantified118 +/- 3 uM details
Detected and Quantified2.6 +/- 0.1 uM details
HMDB IDHMDB0007218
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB094043
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9543716
PDB IDNot Available
ChEBI ID52333
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.