Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-07-07 21:27:06 UTC
Update Date2024-04-30 20:56:11 UTC
Metabolite IDMMDBc0056428
Metabolite Identification
Common NamePA(18:1(9Z)/16:1(9Z))
DescriptionPA(18:1(9Z)/16:1(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(18:1(9Z)/16:1(9Z)), in particular, consists of one 9Z-octadecenoyl chain at the C-1 position and one 9Z-hexadecenoyl 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
Synonyms
ValueSource
1-(9Z-Octadecenoyl)-2-(9Z-hexadecenoyl)-glycero-3-phosphateChEBI
1-Oleoyl-2-palmitoleoyl-sn-glycero-3-phosphateChEBI
1-(9Z-Octadecenoyl)-2-(9Z-hexadecenoyl)-glycero-3-phosphoric acidGenerator
1-Oleoyl-2-palmitoleoyl-sn-glycero-3-phosphoric acidGenerator
1-Oleoyl-2-palmitoleoyl-sn-phosphatidic acidHMDB
PA(18:1/16:1)HMDB
PA(18:1N9/16:1N7)HMDB
PA(18:1W9/16:1W7)HMDB
PA(34:2)HMDB
Phosphatidic acid(18:1(9Z)/16:1(9Z))HMDB
Phosphatidic acid(18:1/16:1)HMDB
Phosphatidic acid(18:1n9/16:1n7)HMDB
Phosphatidic acid(18:1W9/16:1W7)HMDB
Phosphatidic acid(34:2)HMDB
Phosphatidate(18:1(9Z)/16:1(9Z))HMDB
Phosphatidate(18:1/16:1)HMDB
Phosphatidate(18:1N9/16:1N7)HMDB
Phosphatidate(18:1W9/16:1W7)HMDB
Phosphatidate(34:2)HMDB
1-oleoyl-2-palmitoleoyl-sn-glycero-3-phosphate SMPDB, ChEBI
1-oleoyl-2-palmitoleoyl-sn-phosphatidic acid SMPDB, HMDB
PA(18:1/16:1) SMPDB, HMDB
PA(18:1n9/16:1n7) SMPDB, HMDB
PA(18:1w9/16:1w7) SMPDB, HMDB
PA(34:2) SMPDB, HMDB
Phosphatidic acid(18:1(9Z)/16:1(9Z)) SMPDB, HMDB
Phosphatidic acid(18:1/16:1) SMPDB, HMDB
Phosphatidic acid(18:1n9/16:1n7) SMPDB, HMDB
Phosphatidic acid(18:1w9/16:1w7) SMPDB, HMDB
Phosphatidic acid(34:2) SMPDB, HMDB
Phosphatidate(18:1(9Z)/16:1(9Z)) SMPDB, HMDB
Phosphatidate(18:1/16:1) SMPDB, HMDB
Phosphatidate(18:1n9/16:1n7) SMPDB, HMDB
Phosphatidate(18:1w9/16:1w7) SMPDB, HMDB
PA(18:1(9Z)/16:1(9Z))SMPDB
Molecular FormulaC37H69O8P
Average Mass672.925
Monoisotopic Mass672.47300618
IUPAC Name[(2R)-2-[(9Z)-hexadec-9-enoyloxy]-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphonic acid
Traditional Name(2R)-2-[(9Z)-hexadec-9-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)CCCCCCC\C=C/CCCCCC
InChI Identifier
InChI=1S/C37H69O8P/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-36(38)43-33-35(34-44-46(40,41)42)45-37(39)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2/h14,16-18,35H,3-13,15,19-34H2,1-2H3,(H2,40,41,42)/b16-14-,18-17-/t35-/m1/s1
InChI KeyABDVMXLJKAKVKI-YFFVWHPVSA-N