Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-17 23:45:05 UTC
Update Date2024-04-30 19:42:52 UTC
Metabolite IDMMDBc0029873
Metabolite Identification
Common NamePA(18:1(9Z)/18:1(11Z))
DescriptionPA(18:1(9Z)/18:1(11Z)) 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(18:1(9Z)/18:1(11Z)), in particular, consists of one chain of oleic acid at the C-1 position and one chain of vaccenic acid 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
Synonyms
ValueSource
1-(9Z)-Octadecenoyl-2-(11Z)-octadecenoyl-sn-glycero-3-phosphateChEBI
1-Oleoyl-2-(Z)-vaccenoyl-sn-glycero-3-phosphateChEBI
1-Oleoyl-2-vaccenoyl-sn-glycero-3-phosphateChEBI
PA(18:1/18:1)ChEBI
PA(18:1OMEGA9/18:1OMEGA7)ChEBI
PA(36:2)ChEBI
Phosphatidic acid(18:1/18:1)ChEBI
Phosphatidic acid(18:1omega9/18:1omega7)ChEBI
Phosphatidic acid(36:2)ChEBI
1-(9Z)-Octadecenoyl-2-(11Z)-octadecenoyl-sn-glycero-3-phosphoric acidGenerator
1-Oleoyl-2-(Z)-vaccenoyl-sn-glycero-3-phosphoric acidGenerator
1-Oleoyl-2-vaccenoyl-sn-glycero-3-phosphoric acidGenerator
Phosphatidate(18:1/18:1)Generator
Phosphatidate(18:1OMEGA9/18:1OMEGA7)Generator
Phosphatidate(36:2)Generator
Molecular FormulaC39H73O8P
Average Mass700.979
Monoisotopic Mass700.504306309
IUPAC Name[(2R)-2-[(11Z)-octadec-11-enoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphonic acid
Traditional Name(2R)-2-[(11Z)-octadec-11-enoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](COC(=O)CCCCCCC\C=C/CCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C39H73O8P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-31-33-38(40)45-35-37(36-46-48(42,43)44)47-39(41)34-32-30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h14,16-17,19,37H,3-13,15,18,20-36H2,1-2H3,(H2,42,43,44)/b16-14-,19-17-/t37-/m1/s1
InChI KeyWXGVPSHYGAKQHX-YFPMXLMLSA-N