1.0 2011-09-21 01:31:51 UTC 2018-05-29 01:54:22 UTC FDB027912 DHAP(18:0) DHAP(18:0) is the octadecanoyl derivative of Dihydroxyacetone phosphate. It is also known as an alkyl-DHAP. This compound is formed by octadecanoic acid reacting with DHAP. Alkyl-DHAPs are intermediates in the synthesis of ether phospholipids. The initial steps of ether phospholipid biosynthesis take place in peroxisomes. Alkyl-dihydroxyacetonephosphate synthase is the peroxisomal enzyme that actually introduces the ether linkage. Levels of Alkyl-DHAP have been found to be strongly reduced in human fibroblasts derived from Zellweger syndrome and rhizomelic chondrodysplasia punctata patients. Four other enzymes are known to be involved in the metabolism of acyl-DHAP and alkyl-DHAP. These include: acyl-DHAP/alkyl-DHAP oxidoreductase, DHAP acyltransferase, alkyl-DHAP phosphohydrolase, and a dinitrofluorobenzene-insensitive acyl-DHAP acylhydrolase. Dihydroxyacetone phosphate (DHAP) is a biochemical compound primarily involved in the glycolysis metabolic pathway. DHAP is also the product of the dehydrogenation of L-glycerol-3-phosphate which is part of the entry of glycerol (sourced from triglycerides) into the glycolytic pathway. Conversely, reduction of glycolysis-derived DHAP to L-glycerol-3-phosphate provides adipose cells with the activated glycerol backbone they require to synthesize new triglycerides. Both reactions are catalyzed by the enzyme glycerol 3-phosphate dehydrogenase with NAD+/NADH as cofactor. DHAP may be referred to as glycerone phosphate in older texts. 1-Octadecyl-glycerone-3-phosphate is an intermediate in Ether lipid metabolism. DHAP(18:0) or 1-Octadecanoyl-glycerone-3-phosphate is the precursor to 1-Octadecyl-glycerone-3-phosphate DHAP(18:0e) which is generated via alkylglycerone phosphate synthase (EC: 2.5.1.26). Ether lipids are lipids in which one or more of the carbon atoms on glycerol is bonded to an alkyl chain via an ether linkage, as opposed to the usual ester linkage. Ether lipids are called plasmalogens (1-O-1'-alkenyl-2-acylglycerophospholipids) if these are glycerol-containing phospholipids with an unsaturated O-(1-alkenyl) (vinyl ether) group at the first position on the glycerol chain. Plasmalogens as well as some 1-O-alkyl lipids are ubiquitous and sometimes major parts of the cell membranes in mammals and anaerobic bacteria. In archaea, ether lipids are the major polar lipids in the cell envelope and their abundance is one of the major characteristics that separate this group of prokaryotes from the bacteria. In these cells, diphytanylglycerolipids or bipolar macrocyclic tetraethers can form covalently linked 'bilayers'. [HMDB] 1-Octadecanoyl DHAP 1-Octadecanoyl dihydroxyacetone ate 1-Octadecanoyl Dihydroxyacetone phosphate 1-Octadecanoyl-glycerone-3-ate 1-Octadecanoyl-glycerone-3-phosphate 1-Stearoylglycerone 3-ate 1-stearoylglycerone 3-phosphate C21H41O7P 436.5198 436.258990178 [3-(octadecanoyloxy)-2-oxopropoxy]phosphonic acid stearoylglycerone phosphate CCCCCCCCCCCCCCCCCC(=O)OCC(=O)COP(O)(O)=O InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h2-19H2,1H3,(H2,24,25,26) GTPATKZCXDKGQS-UHFFFAOYSA-N belongs to the class of organic compounds known as o-acylglycerone-phosphates. These are glycerone-3-phosphates carrying an acyl substituent at the 1-position. O-acylglycerone-phosphates Organic compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Aliphatic acyclic compounds Alpha-acyloxy ketones Carboxylic acid esters Fatty acid esters Hydrocarbon derivatives Monoalkyl phosphates Monocarboxylic acids and derivatives Monosaccharide phosphates Organic oxides Aliphatic acyclic compound Alkyl phosphate Alpha-acyloxy ketone Carboxylic acid derivative Carboxylic acid ester Fatty acid ester Fatty acyl Hydrocarbon derivative Monoalkyl phosphate Monocarboxylic acid or derivatives Monosaccharide Monosaccharide phosphate O-acylglycerone-phosphate Organic oxide Organic phosphoric acid derivative Phosphoric acid ester Solid logp 5.37 ALOGPS logs -5.71 ALOGPS solubility 8.47e-04 g/l ALOGPS logp 6.16 ChemAxon pka_strongest_acidic 1.19 ChemAxon pka_strongest_basic -7 ChemAxon iupac [3-(octadecanoyloxy)-2-oxopropoxy]phosphonic acid ChemAxon average_mass 436.5198 ChemAxon mono_mass 436.258990178 ChemAxon smiles CCCCCCCCCCCCCCCCCC(=O)OCC(=O)COP(O)(O)=O ChemAxon formula C21H41O7P ChemAxon inchi InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h2-19H2,1H3,(H2,24,25,26) ChemAxon inchikey GTPATKZCXDKGQS-UHFFFAOYSA-N ChemAxon polar_surface_area 110.13 ChemAxon refractivity 113.27 ChemAxon polarizability 50.42 ChemAxon rotatable_bond_count 22 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Plasmalogen Synthesis SMP00479 Specdb::CMs 9592 Specdb::CMs 137228 Specdb::CMs 144962 Specdb::MsMs 287161 Specdb::MsMs 287162 Specdb::MsMs 287163 Specdb::MsMs 325924 Specdb::MsMs 325925 Specdb::MsMs 325926 Specdb::MsMs 2772647 Specdb::MsMs 2772648 Specdb::MsMs 2772649 Specdb::MsMs 2909654 Specdb::MsMs 2909655 Specdb::MsMs 2909656 HMDB11133 Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823