2-(Hexadecanoyloxy)-1-[(phosphonooxy)methyl]ethyl hexadecanoate
PubChem CID: 446066
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| Compound Synonyms | 7091-44-3, 1,2-Dipalmitoyl-sn-glycerol 3-phosphate, Dipalmitoyl, dipalmitoyl phosphatidic acid, 1,2-Dipalmitoyl-3-sn-phosphatidic acid, phosphatidic acid, L-A-PHOSPHATIDIC ACID, DIPALMITOYL*FREE ACID, dipalmitoylphosphatidic acid, 1,2-Dipalmitoyl-sn-glycerol-3-phosphoric acid, PA(16:0/16:0), [(2R)-2-hexadecanoyloxy-3-phosphonooxypropyl] hexadecanoate, Phosphatidic acid(32:0), Phosphatidic acid(16:0/16:0), 2-(HEXADECANOYLOXY)-1-[(PHOSPHONOOXY)METHYL]ETHYL HEXADECANOATE, L-alpha-Dipalmitoylphosphatidic acid, 1,2-dihexadecanoyl-sn-glycero-3-phosphate, Dipalmitoyl-L-alpha-phosphatidic acid, 1,2-dihexadecanoyl-sn-glycerol-3-phosphate, Palmitin, 1,2-di-, dihydrogen phosphate, L-, 1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphoric acid, (2R)-3-(phosphonooxy)propane-1,2-diyl dihexadecanoate, Hexadecanoic acid, 1-[(phosphonooxy)methyl]-1,2-ethanediyl ester, (R)-, PA(32:0), Dipalmitoylphosphatidate, L-a-Dipalmitoylphosphatidate, SCHEMBL44215, Dipalmitoyl-L-a-phosphatidate, L-a-Dipalmitoyl-phosphatidate, L-alpha-Dipalmitoylphosphatidate, L-a-Dipalmitoylphosphatidic acid, CHEBI:73246, Dipalmitoyl-L-alpha-phosphatidate, L-alpha-Dipalmitoyl-phosphatidate, Dipalmitoyl-L-a-phosphatidic acid, L-a-Dipalmitoyl-phosphatidic acid, PORPENFLTBBHSG-MGBGTMOVSA-N, DTXSID101301555, 1,2-Dipalmitoyl-3-sn-phosphatidate, L-I+/--Dipalmitoylphosphatidic acid, L-alpha-Dipalmitoyl-phosphatidic acid, LMGP10010027, AKOS040732217, 16:0 PA, 1,2-dihexadecanoyl-rac-phosphatidic acid, 1,2-dipalmitoyl-sn-glycerol-3-phosphate, PD101874, 1,2-Dipalmitoyl-sn-glycerol-3-phosphorate, HY-113437, CS-0059528, NS00124440, 1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphorate, (R)-3-(Phosphonooxy)propane-1,2-diyl dipalmitate, Palmitin, 1,2-di-, dihydrogen phosphate, L- (8CI), Q27140395, Hexadecanoic acid, 1-[(phosphonooxy)methyl]-1,2-ethanediyl ester,(R)-, Hexadecanoic acid, (1R)-1-[(phosphonooxy)methyl]-1,2-ethanediyl ester(9CI), hexadecanoic acid, (1R)-2-[(1-oxohexadecyl)oxy]-1-[(phosphonooxy)methyl]ethyl ester |
|---|---|
| Topological Polar Surface Area | 119.0 |
| Hydrogen Bond Donor Count | 2.0 |
| Heavy Atom Count | 44.0 |
| Pathway Kegg Map Id | map00561, map00564 |
| Description | PA(16:0/16:0) is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids 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. PA(16:0/16:0), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of palmitic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. Indeed, the concentration of phosphatidic acids is often over-estimated in tissues and biofluids as it can arise by inadvertent enzymatic hydrolysis during inappropriate storage or extraction conditions during analysis. The main biosynthetic route of phosphatidic acid in animal tissues involves sequential acylation of alpha-glycerophosphate by acyl-coA derivatives of fatty acids. PAs are biologically active lipids that can stimulate a large range of responses in many different cell types, such as platelet aggregation, smooth muscle contraction, in vivo vasoactive effects, chemotaxis, expression of adhesion molecules, increased tight junction permeability of endothelial cells, induction of stress fibres, modulation of cardiac contractility, and many others. Diacylglycerols (DAGs) can be converted to PAs by DAG kinases and indirect evidence supports the notion that PAs alter the excitability of neurons. Phospholipase Ds (PLDs), which catalyze the conversion of glycerolphospholipids, particularly phosphatidylcholine, to PAs and the conversion of N-arachidonoyl-phosphatidylethanolamine (NAPE) to anandamide and PAs are activated by several inflammatory mediators including bradykinin, ATP and glutamate. PAs activate downstream signaling pathways such as PKCs and mitogen-activated protein kinases (MAPKs), which are linked to an increase in sensitivity of sensory neurons either during inflammation or in chronic pain models. Circumstantial evidence that PAs are converted to DAGs. (PMID: 12618218, 16185776). [HMDB] |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 696.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 1.0 |
| Enzyme Uniprot Id | O14939, Q8NEL9, O95674, Q9NRZ7, O15120, Q99943, P80108, Q9NUQ2, Q3SYC2, Q9NRZ5, Q6UWP7, Q7Z2D5, Q32ZL2, Q8IY26, Q8NBV4, Q5VZY2, Q8NEB5, A1L4Q0, O94830 |
| Iupac Name | [(2R)-2-hexadecanoyloxy-3-phosphonooxypropyl] hexadecanoate |
| Prediction Hob | 0.0 |
| Class | Glycerophospholipids |
| Xlogp | 12.9 |
| Superclass | Lipids and lipid-like molecules |
| Subclass | Glycerophosphates |
| Molecular Formula | C35H69O8P |
| Prediction Swissadme | 0.0 |
| Inchi Key | PORPENFLTBBHSG-MGBGTMOVSA-N |
| Fcsp3 | 0.9428571428571428 |
| Rotatable Bond Count | 36.0 |
| State | Solid |
| Synonyms | 1,2-Di-O-palmitoyl-3-sn-glyceryl-O-orate, 1,2-Di-O-palmitoyl-3-sn-glyceryl-O-oric acid, 1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphorate, 1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphoric acid, 1,2-Dihexadecanoyl-rac-atidic acid, 1,2-dihexadecanoyl-rac-phosphatidic acid, 1,2-Dipalmitoyl-3-sn-atidate, 1,2-Dipalmitoyl-3-sn-atidic acid, 1,2-Dipalmitoyl-3-sn-phosphatidate, 1,2-Dipalmitoyl-3-sn-phosphatidic acid, 1,2-Dipalmitoyl-sn-glycerol 3-ate, 1,2-Dipalmitoyl-sn-glycerol 3-phosphate, 1,2-Dipalmitoyl-sn-glycerol-3-ate, 1,2-Dipalmitoyl-sn-glycerol-3-ic acid, 1,2-Dipalmitoyl-sn-glycerol-3-orate, 1,2-Dipalmitoyl-sn-glycerol-3-oric acid, 1,2-Dipalmitoyl-sn-glycerol-3-phosphorate, 1,2-Dipalmitoyl-sn-glycerol-3-phosphoric acid, Atidate(16:0/16:0), Atidate(32:0), Atidic acid(16:0/16:0), Atidic acid(32:0), Dipalmitoyl atidate, Dipalmitoyl atidic acid, Dipalmitoyl-L-a-atidate, Dipalmitoyl-L-a-atidic acid, Dipalmitoyl-L-a-phosphatidate, Dipalmitoyl-L-a-phosphatidic acid, Dipalmitoyl-L-alpha-atidate, Dipalmitoyl-L-alpha-atidic acid, Dipalmitoyl-L-alpha-phosphatidate, Dipalmitoyl-L-alpha-phosphatidic acid, Dipalmitoylatidate, Dipalmitoylatidic acid, Dipalmitoylphosphatidate, Dipalmitoylphosphatidic acid, L-a-Dipalmitoyl-atidate, L-a-Dipalmitoyl-atidic acid, L-a-Dipalmitoyl-phosphatidate, L-a-Dipalmitoyl-phosphatidic acid, L-a-Dipalmitoylatidate, L-a-Dipalmitoylatidic acid, L-a-Dipalmitoylphosphatidate, L-a-Dipalmitoylphosphatidic acid, L-alpha-Dipalmitoyl-atidate, L-alpha-Dipalmitoyl-atidic acid, L-alpha-Dipalmitoyl-phosphatidate, L-alpha-Dipalmitoyl-phosphatidic acid, L-alpha-Dipalmitoylatidate, L-alpha-Dipalmitoylatidic acid, L-alpha-Dipalmitoylphosphatidate, L-alpha-Dipalmitoylphosphatidic acid, PA(32:0), Phosphatidic acid(16:0/16:0), Phosphatidic acid(32:0) |
| Substituent Name | 1,2-diacylglycerol-3-phosphate, Monoalkyl phosphate, Fatty acid ester, Fatty acyl, Alkyl phosphate, Phosphoric acid ester, Organic phosphoric acid derivative, Organic phosphate, Dicarboxylic acid or derivatives, Carboxylic acid ester, Ether, Carboxylic acid derivative, Hydrocarbon derivative, Organooxygen compound, Carbonyl group, Aliphatic acyclic compound |
| Compound Name | 2-(Hexadecanoyloxy)-1-[(phosphonooxy)methyl]ethyl hexadecanoate |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 648.473 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 648.473 |
| Hydrogen Bond Acceptor Count | 8.0 |
| Molecular Weight | 648.9 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 1.0 |
| Total Bond Stereocenter Count | 0.0 |
| Esol | -9.645698599999996 |
| Inchi | InChI=1S/C35H69O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-34(36)41-31-33(32-42-44(38,39)40)43-35(37)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h33H,3-32H2,1-2H3,(H2,38,39,40)/t33-/m1/s1 |
| Smiles | CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O)OC(=O)CCCCCCCCCCCCCCC |
| Defined Bond Stereocenter Count | 0.0 |
- 1. Outgoing r'ship
FOUND_INto/from Vitis Vinifera (Plant) Rel Props:Source_db:cmaup_ingredients;npass_chem_all