Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-07-07 22:08:11 UTC
Update Date2023-12-14 16:53:55 UTC
Metabolite IDMMDBc0056929
Metabolite Identification
Common NamePA(18:0/19:1(9Z))
DescriptionPA(18:0/19:1(9Z)) 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(18:0/19:1(9Z)), in particular, consists of one octadecanoyl chain at the C-1 position and one 9Z-nonadecenoyl chain at the C-2 position. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. PAs are biologically active lipids that can stimulate a large range of responses in many different cell types. Diacylglycerols (DAGs) can be converted to PAs by DAG kinases. 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). Circumstantial evidence that PAs are converted to DAGs. (PMID: 12618218 , 16185776 ).
Structure
SynonymsNot Available
Molecular FormulaC40H77O8P
Average Mass717.022
Monoisotopic Mass716.535606437
IUPAC Name[(2R)-2-[(9Z)-nonadec-9-enoyloxy]-3-(octadecanoyloxy)propoxy]phosphonic acid
Traditional Name(2R)-2-[(9Z)-nonadec-9-enoyloxy]-3-(octadecanoyloxy)propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCC\C=C/CCCCCCCCC
InChI Identifier
InChI=1S/C40H77O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-35-40(42)48-38(37-47-49(43,44)45)36-46-39(41)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h19,21,38H,3-18,20,22-37H2,1-2H3,(H2,43,44,45)/b21-19-/t38-/m1/s1
InChI KeyDFMAHWOLVYAWKZ-IOSXAPFHSA-N