Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2008-09-12 01:12:51 UTC |
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Update Date | 2022-11-30 19:02:48 UTC |
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HMDB ID | HMDB0007001 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | CDP-DG(18:1(9Z)/22:3(10Z,13Z,16Z)) |
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Description | CDP-DG(18:1(9Z)/22:3(10Z,13Z,16Z)) is a cytidine diphosphate diacylglycerol or CDP-diacylglycerol. CDP-diacylglycerol (CDP-DG) is an important branchpoint intermediate in eukaryotic phospholipid biosynthesis and could be a key regulatory molecule in phospholipid metabolism. It is a glycerophospholipid in which a cytidine diphosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, CDP-diacylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. CDP-DG(18:1(9Z)/22:3(10Z,13Z,16Z)), in particular, consists of one chain of oleic acid at the C-1 position and one chain of (10Z,13Z,16Z-docosatrienoyl) at the C-2 position. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the (10Z,13Z,16Z-docosatrienoyl) moiety is derived from fish oils. CDP-diacylglycerols are intermediates in the synthesis of phosphatidylglycerols (PG, PC, PS, PI), which is catalyzed by CDP-diacyl synthase, synthase, phosphatidylglycerolphosphate (PGP) synthase, phosphatidylinositol (PI) synthase, and phosphatidylserine (PS) synthase. Cytidine diphosphate diacylglycerols are rarely noticed in analyses of lipid compositions of tissues, as they are present is such small amounts, perhaps only 0.05% or so of the total phospholipids. |
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Structure | [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCC\C=C/C\C=C/C\C=C/CCCCC InChI=1S/C52H89N3O15P2/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-48(57)68-44(41-65-47(56)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2)42-66-71(61,62)70-72(63,64)67-43-45-49(58)50(59)51(69-45)55-40-39-46(53)54-52(55)60/h11,13,17-19,21-23,39-40,44-45,49-51,58-59H,3-10,12,14-16,20,24-38,41-43H2,1-2H3,(H,61,62)(H,63,64)(H2,53,54,60)/b13-11-,19-17-,22-21-,23-18-/t44-,45-,49+,50?,51-/m1/s1 |
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Synonyms | Value | Source |
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1-(9Z-Octadecenoyl)-2-(10Z,13Z,16Z-docosatrienoyl)-sn-glycero-3-CDP | HMDB | 1-Oleoyl-2-(10Z,13Z,16Z-docosatrienoyl)-sn-glycero-3-cytidine-5'-diphosphate | HMDB | CDP-DG(18:1/22:3) | HMDB | CDP-DG(18:1N9/22:3N6) | HMDB | CDP-DG(18:1W9/22:3W6) | HMDB | CDP-DG(40:4) | HMDB | CDP-Diacylglycerol(18:1/22:3) | HMDB | CDP-Diacylglycerol(18:1N9/22:3N6) | HMDB | CDP-Diacylglycerol(18:1W9/22:3W6) | HMDB | CDP-Diacylglycerol(40:4) | HMDB |
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Chemical Formula | C52H89N3O15P2 |
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Average Molecular Weight | 1058.2217 |
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Monoisotopic Molecular Weight | 1057.576892217 |
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IUPAC Name | [({[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy][(2R)-2-[(10Z,13Z,16Z)-docosa-10,13,16-trienoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphinic acid |
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Traditional Name | {[(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(2R)-2-[(10Z,13Z,16Z)-docosa-10,13,16-trienoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxyphosphinic acid |
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CAS Registry Number | Not Available |
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SMILES | [H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H](C(O)[C@H]1O)N1C=CC(N)=NC1=O)OC(=O)CCCCCCCC\C=C/C\C=C/C\C=C/CCCCC |
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InChI Identifier | InChI=1S/C52H89N3O15P2/c1-3-5-7-9-11-13-15-17-19-20-21-22-24-26-28-30-32-34-36-38-48(57)68-44(41-65-47(56)37-35-33-31-29-27-25-23-18-16-14-12-10-8-6-4-2)42-66-71(61,62)70-72(63,64)67-43-45-49(58)50(59)51(69-45)55-40-39-46(53)54-52(55)60/h11,13,17-19,21-23,39-40,44-45,49-51,58-59H,3-10,12,14-16,20,24-38,41-43H2,1-2H3,(H,61,62)(H,63,64)(H2,53,54,60)/b13-11-,19-17-,22-21-,23-18-/t44-,45-,49+,50?,51-/m1/s1 |
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InChI Key | KTDSFHYGTNRDNM-CHNQJESLSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 1-acyl-sn-glycerol-2,3-cyclic-phosphates. These are monoacylglycerophosphates consisting of a sn-glycerol 2,3-cyclic phosphate that carries an acyl group at the 1-position. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Glycerophospholipids |
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Sub Class | Glycerophosphates |
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Direct Parent | 1-acyl-sn-glycerol-2,3-cyclic-phosphates |
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Alternative Parents | |
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Substituents | - 1-acyl-sn-glycerol-2,3-cyclic-phosphate
- Fatty acid ester
- Organic phosphoric acid derivative
- Fatty acyl
- 1,3_dioxaphospholane
- Carboxylic acid ester
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Oxacycle
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Organooxygen compound
- Organic oxygen compound
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesNot Available | Show more...
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