Structure Database (LMSD)
Common Name
DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2]
Systematic Name
1-octadecanoyl-2-(5Z,8Z,11Z,14Z-eicosatetraenoyl)-sn-glycerol
Synonyms
- DG(18:0/20:4/0:0)[iso2]
- DG(38:4)
- DG(18:0_20:4)
3D model of DG(18:0/20:4(5Z,8Z,11Z,14Z)/0:0)[iso2]
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
Many protein kinase C (PKC) isoforms require activation via second messengers including Ca2+, diacylglycerol (DAG), and/or a phospholipid to phosphorylate target proteins and they initiate a variety of important signalling cascades.1 1-Stearoyl-2-arachidonoyl-sn-glycerol (SAG) is a DAG that contains the ω-6 polyunsaturated fatty acid arachidonic acid in the sn-2 position and stearic acid in the sn-1 position of the glycerol backbone. It can potently activate PKCα, PKCε, and PKCδ at nM concentrations.2 Independent of PKC signalling, SAG competitively binds to the Ras activator RasGRP with a Ki value of 4.49 µM in Jurkat T-cells.3
This information has been provided by Cayman Chemical
References
1. Bell, R.M., and Burns, D.J. Lipid activation of protein kinase C. The Journal of Biological Chemisty 266(8), 4661-4664 (1991).
2. Madani, S., Hichami, A., Charkaoui-Malki, M., et al. Diacylglycerols containing ω-3 and ω-6 fatty acids bind to RasGRP and modulate MAP kinase activation. The Journal of Biological Chemisty 279(2), 1176-1183 (2004).
3. Madani, S., Hichami, A., Legrand, A., et al. Implication of acyl chain diacylglycerols in activation of different isoforms of protein kinase C. FASEB J. 15(14), 2595-2601 (2001).
Reactions
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String Representations
InChiKey (Click to copy)
NSXLMTYRMFVYNT-IUJDHQGTSA-N
InChi (Click to copy)
InChI=1S/C41H72O5/c1-3-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-36-41(44)46-39(37-42)38-45-40(43)35-33-31-29-27-25-23-21-18-16-14-12-10-8-6-4-2/h11,13,17,19,22,24,28,30,39,42H,3-10,12,14-16,18,20-21,23,25-27,29,31-38H2,1-2H3/b13-11-,19-17-,24-22-,30-28-/t39-/m0/s1
SMILES (Click to copy)
OC[C@]([H])(OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O)COC(CCCCCCCCCCCCCCCCC)=O
Other Databases
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
46
Rings
0
Aromatic Rings
0
Rotatable Bonds
36
Van der Waals Molecular Volume
745.97
Topological Polar Surface Area
72.83
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
5
logP
12.70
Molar Refractivity
197.37
Admin
Created at
-
Updated at
25th Apr 2022
LIPID MAPS® abbreviations for glycerolipids (GL)
The LIPID MAPS® glycerolipid abbreviations (MG,DG,TG) are used here to refer to species with one, two or three radyl side-chains, respectively, where the structures of the side chains are indicated within parentheses in the 'Prefix(sn1/sn2/sn3)' format (e.g. TG(16:0/18:1(9Z)/18:0). Acyl chains are assumed by default. The alkyl ether linkage is represented by the 'O-' prefix, e.g. DG(O-16:0/18:1(9Z)/0:0), whereas the 1Z-alkenyl ether (Plasmalogen) linkage is represented by the 'P-' prefix, e.g. and DG(P-14:0/18:1(9Z)/0:0).
For Diradylglycerols and Triradylglycerols, it is not always possible to experimentally determine the exact position of radyl groups on the glycerol group. For Diradylglycerols with two different radyl groups, two different structural isomers exist. For Triradylglycerols with three different radyl groups, six different isomers exist.
Instead of drawing all possible structural isomers explicitly for Diradylglycerols and Triradylglycerols, the LIPID MAPS® abbreviation scheme supports the isomeric specification. A suffix containing 'iso' along with the number of possible isomers is appended to the abbreviation (e.g. [iso2],[iso6]) and a single unique LM_ID is assigned. The structure assigned to the LM_ID corresponds to the radyl substitution shown in the abbreviation. An option is provided to display the other isomers in the group.
The [rac] designation refers to racemic mixtures due to substitution at the sn1 and sn3 positions of glycerol.
The LIPID MAPS® glycerolipid abbreviations (MG,DG,TG) are used here to refer to species with one, two or three radyl side-chains, respectively, where the structures of the side chains are indicated within parentheses in the 'Prefix(sn1/sn2/sn3)' format (e.g. TG(16:0/18:1(9Z)/18:0). Acyl chains are assumed by default. The alkyl ether linkage is represented by the 'O-' prefix, e.g. DG(O-16:0/18:1(9Z)/0:0), whereas the 1Z-alkenyl ether (Plasmalogen) linkage is represented by the 'P-' prefix, e.g. and DG(P-14:0/18:1(9Z)/0:0).
For Diradylglycerols and Triradylglycerols, it is not always possible to experimentally determine the exact position of radyl groups on the glycerol group. For Diradylglycerols with two different radyl groups, two different structural isomers exist. For Triradylglycerols with three different radyl groups, six different isomers exist.
Instead of drawing all possible structural isomers explicitly for Diradylglycerols and Triradylglycerols, the LIPID MAPS® abbreviation scheme supports the isomeric specification. A suffix containing 'iso' along with the number of possible isomers is appended to the abbreviation (e.g. [iso2],[iso6]) and a single unique LM_ID is assigned. The structure assigned to the LM_ID corresponds to the radyl substitution shown in the abbreviation. An option is provided to display the other isomers in the group.
The [rac] designation refers to racemic mixtures due to substitution at the sn1 and sn3 positions of glycerol.