Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000169
Name: PA(16:0/16:0)
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. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids. 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. Circumstantial evidence that PAs are converted to DAGs. (PMID: 12618218, 16185776).
  • 1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphate
  • 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-phosphatidate
  • 1,2-Dihexadecanoyl-rac-phosphatidic acid
  • 1,2-Dipalmitoyl-3-sn-phosphatidate
  • 1,2-Dipalmitoyl-3-sn-phosphatidic acid
  • 1,2-Dipalmitoyl-sn-glycerol 3-phosphate
  • 1,2-Dipalmitoyl-sn-glycerol 3-phosphoric acid
  • 1,2-Dipalmitoyl-sn-glycerol-3-phosphate
  • 1,2-Dipalmitoyl-sn-glycerol-3-phosphorate
  • 1,2-Dipalmitoyl-sn-glycerol-3-phosphoric acid
  • A 1,2-diacylglycerol-3-phosphate
  • a 1,2-Diacylglycerol-3-phosphoric acid
  • A 3-sn-phosphatidate
  • a 3-sn-Phosphatidate
  • a 3-sn-Phosphatidic acid
  • A diacyl-glycerol-3p
  • A diacyl-glycerol-p
  • A diacylglycerol-3-phosphate
  • a Diacylglycerol-3-phosphoric acid
  • A phosphatidate
  • A phosphatidic acid
  • A phosphatidylglycerol
  • An L-phosphatidate
  • An L-phosphatidic acid
  • DGP
  • Diacylglycerol phosphate
  • Diacylglycerol phosphoric acid
  • Dipalmitoyl-L-a-phosphatidate
  • Dipalmitoyl-L-a-phosphatidic acid
  • Dipalmitoyl-L-alpha-phosphatidate
  • Dipalmitoyl-L-alpha-phosphatidic acid
  • Dipalmitoyl-L-α-phosphatidate
  • Dipalmitoyl-L-α-phosphatidic acid
  • Dipalmitoylphosphatidate
  • Dipalmitoylphosphatidic acid
  • L-a-Dipalmitoyl-phosphatidate
  • L-a-Dipalmitoyl-phosphatidic acid
  • L-a-Dipalmitoylphosphatidate
  • L-a-Dipalmitoylphosphatidic acid
  • L-alpha-Dipalmitoyl-phosphatidate
  • L-alpha-Dipalmitoyl-phosphatidic acid
  • L-alpha-Dipalmitoylphosphatidate
  • L-alpha-Dipalmitoylphosphatidic acid
  • L-α-Dipalmitoyl-phosphatidate
  • L-α-Dipalmitoyl-phosphatidic acid
  • L-α-Dipalmitoylphosphatidate
  • L-α-Dipalmitoylphosphatidic acid
  • PA(32:0)
  • Phosphatidate(16:0/16:0)
  • Phosphatidate(32:0)
  • Phosphatidic acid(16:0/16:0)
  • Phosphatidic acid(32:0)
Chemical Formula: C35H69O8P
Average Molecular Weight: 648.8913
Monoisotopic Molecular Weight: 648.473005696
CAS number: 7091-44-3
IUPAC Name:[(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphonic acid
Traditional IUPAC Name: dipalmitoyl
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as 1,2-diacylglycerol-3-phosphates. These are glycerol-3-phosphates in which the glycerol moiety is bonded to two aliphatic chains through ester linkages.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Glycerophospholipids
Sub ClassGlycerophosphates
Direct Parent 1,2-diacylglycerol-3-phosphates
Alternative Parents
  • 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
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Melting point: 161-165 °C
Experimental Properties:
Predicted Properties
Water Solubility0.000118 mg/mLALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area119.36 Å2ChemAxon
Rotatable Bond Count36ChemAxon
Refractivity178.57 m3·mol-1ChemAxon
Polarizability80.09 Å3ChemAxon
Number of Rings0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Membrane
Water + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (dihexadecanoyl, n-C16:0) + Phosphate
Water + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (dioctadec-11-enoyl, n-C18:1) + Phosphate
Water + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (ditetradec-7-enoyl, n-C14:1) + Phosphate
Water + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (ditetradecanoyl, n-C14:0) + Phosphate
1-Dodecanoyl-sn-glycerol 3-phosphate + Dodecanoyl-ACP (n-C12:0ACP) > acyl carrier protein + PA(16:0/16:0)
1-Hexadec-9-enoyl-sn-glycerol 3-phosphate + cis-hexadec-9-enoyl-[acyl-carrier protein] (n-C16:1) > acyl carrier protein + PA(16:0/16:0)
1-hexadecanoyl-sn-glycerol 3-phosphate + Palmitoyl-ACP (n-C16:0ACP) > acyl carrier protein + PA(16:0/16:0)
1-Octadec-11-enoyl-sn-glycerol 3-phosphate + cis-octadec-11-enoyl-[acyl-carrier protein] (n-C18:1) > acyl carrier protein + PA(16:0/16:0)
1-Octadecanoyl-sn-glycerol 3-phosphate + Octadecanoyl-ACP (n-C18:0ACP) > acyl carrier protein + PA(16:0/16:0)
1-Tetradec-7-enoyl-sn-glycerol 3-phosphate + cis-tetradec-7-enoyl-[acyl-carrier protein] (n-C14:1) > acyl carrier protein + PA(16:0/16:0)
1-Tetradecanoyl-sn-glycerol 3-phosphate + Myristoyl-ACP (n-C14:0ACP) > acyl carrier protein + PA(16:0/16:0)
Water + PA(16:0/16:0) > 1-Dodecanoyl-sn-glycerol 3-phosphate + Dodecanoate (N-C12:0) + Hydrogen ion
Water + PA(16:0/16:0) > 1-hexadecanoyl-sn-glycerol 3-phosphate + Hydrogen ion + Palmitic acid
Water + PA(16:0/16:0) > 1-Octadec-11-enoyl-sn-glycerol 3-phosphate + Hydrogen ion + Octadecenoate (N-C18:1)
Water + PA(16:0/16:0) > 1-Octadecanoyl-sn-glycerol 3-phosphate + Hydrogen ion + Octadecanoate (N-C18:0)
Water + PA(16:0/16:0) > 1-Tetradec-7-enoyl-sn-glycerol 3-phosphate + Hydrogen ion + Tetradecenoate (N-C14:1)
Water + PA(16:0/16:0) > 1-Tetradecanoyl-sn-glycerol 3-phosphate + Hydrogen ion + tetradecanoate (n-C14:0)
Water + PA(16:0/16:0) > 2-dodecanoyl-sn-glycerol 3-phosphate + Dodecanoate (N-C12:0)
Water + PA(16:0/16:0) > 2-hexadecanoyl-sn-glycerol 3-phosphate + Palmitic acid
Water + PA(16:0/16:0) > 2-octadec-11-enoyl-sn-glycerol 3-phosphate + Octadecenoate (N-C18:1)
Water + PA(16:0/16:0) > 2-octadecanoyl-sn-glycerol 3-phosphate + Octadecanoate (N-C18:0)
Water + PA(16:0/16:0) > 2-tetradec-7-enoyl-sn-glycerol 3-phosphate + Tetradecenoate (N-C14:1)
Water + PA(16:0/16:0) > 2-tetradecanoyl-sn-glycerol 3-phosphate + tetradecanoate (n-C14:0)
CDP-1,2-didodecanoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0)
CDP-1,2-dihexadec-9-enoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0)
CDP-1,2-dihexadecanoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0)
CDP-1,2-dioctadec-11-enoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0)
CDP-1,2-Dioctadecanoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0)
CDP-1,2-ditetradec-7-enoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0)
CDP-1,2-ditetradecanoylglycerol + Water > Cytidine monophosphate +2 Hydrogen ion + PA(16:0/16:0)
1,2-Diacyl-sn-glycerol (didodecanoyl, n-C12:0) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0)
1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0)
1,2-Diacyl-sn-glycerol (dihexadecanoyl, n-C16:0) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0)
1,2-Diacyl-sn-glycerol (dioctadec-11-enoyl, n-C18:1) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0)
1,2-Diacyl-sn-glycerol (ditetradec-7-enoyl, n-C14:1) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0)
1,2-Diacyl-sn-glycerol (ditetradecanoyl, n-C14:0) + Adenosine triphosphate > ADP + Hydrogen ion + PA(16:0/16:0)
CDP-diacylglycerol + Water <> Cytidine monophosphate + PA(16:0/16:0)
Cytidine triphosphate + PA(16:0/16:0) <> Pyrophosphate + CDP-diacylglycerol
Adenosine triphosphate + 1,2-Diacyl-sn-glycerol + 1,2-Diacyl-sn-glycerol <> ADP + PA(16:0/16:0)
PA(16:0/16:0) + Coenzyme A + Acyl-CoA + 1-Acyl-sn-glycerol 3-phosphate <> 1-Acyl-sn-glycerol 3-phosphate + Acyl-CoA
Acyl-[acyl-carrier protein] + 1-Acyl-sn-glycerol 3-phosphate <> Acyl-carrier protein + PA(16:0/16:0)
a 1,2-diacyl-<i>sn</i>-glycerol 3-diphosphate + Water PA(16:0/16:0) + Phosphate + Hydrogen ion
a CDP-diacylglycerol + Water <> PA(16:0/16:0) + Cytidine monophosphate + Hydrogen ion
Cytidine triphosphate + PA(16:0/16:0) + Hydrogen ion > Pyrophosphate + a CDP-diacylglycerol
Adenosine triphosphate + a 1,2-diacylglycerol <> Hydrogen ion + PA(16:0/16:0) + ADP
a 1-acyl-<i>sn</i>-glycerol-3-phosphate + a long-chain acyl-CoA > Coenzyme A + PA(16:0/16:0)

Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0002-0000009000-b3b708036c56c15fec89View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-1492100000-5624ed03f664b67f79ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4i-1490000000-1ba8a217ef22599ee07cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • Niedernberg, A., Tunaru, S., Blaukat, A., Ardati, A., Kostenis, E. (2003). "Sphingosine 1-phosphate and dioleoylphosphatidic acid are low affinity agonists for the orphan receptor GPR63." Cell Signal 15:435-446. Pubmed: 12618218
  • Park KA, Vasko MR: Lipid mediators of sensitivity in sensory neurons. Trends Pharmacol Sci. 2005 Nov;26(11):571-7. Epub 2005 Sep 26. Pubmed: 16185776
  • Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. Thesis. Villanova University: U.S.A
Synthesis Reference: Ando, Yoshihiro; Oda, Hiroshi; Matsuyoshi, Shigeru; Maekawa, Naoya. Manufacture of phosphatidic acid alkali metal or ammonium salts using phospholipase D. Jpn. Kokai Tokkyo Koho (2001), 8 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
Pubchem Compound ID446066
Kegg IDC00416
ChemSpider ID393518
Wikipedia IDNot Available
Ligand ExpoPX6


General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
CTP + phosphatidate = diphosphate + CDP- diacylglycerol
Gene Name:
Locus Tag:
Molecular weight:
28.9 kDa
CTP + phosphatidate = diphosphate + CDP-diacylglycerol.
General function:
Involved in diacylglycerol kinase activity
Specific function:
Recycling of diacylglycerol produced during the turnover of membrane phospholipid
Gene Name:
Locus Tag:
Molecular weight:
13.1 kDa
ATP + 1,2-diacylglycerol = ADP + 1,2-diacyl-sn-glycerol 3-phosphate.
General function:
Involved in nucleotide binding
Specific function:
Involved in lipid A export and possibly also in glycerophospholipid export and for biogenesis of the outer membrane. Transmembrane domains (TMD) form a pore in the inner membrane and the ATP-binding domain (NBD) is responsible for energy generation
Gene Name:
Locus Tag:
Molecular weight:
66.4 kDa


General function:
Involved in nucleotide binding
Specific function:
Involved in lipid A export and possibly also in glycerophospholipid export and for biogenesis of the outer membrane. Transmembrane domains (TMD) form a pore in the inner membrane and the ATP-binding domain (NBD) is responsible for energy generation
Gene Name:
Locus Tag:
Molecular weight:
66.4 kDa
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Part of the ABC transporter complex mlaFEDB that actively prevents phospholipid accumulation at the cell surface. Probably maintains lipid asymmetry in the outer membrane by retrograde trafficking of phospholipids from the outer membrane to the inner membrane
Gene Name:
Locus Tag:
Molecular weight:
28.4 kDa