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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2018-05-19 22:09:25 UTC
HMDB IDHMDB0000674
Secondary Accession Numbers
  • HMDB0007857
  • HMDB00674
  • HMDB07857
Metabolite Identification
Common NamePA(16:0/16:0)
DescriptionPA(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 ).
Structure
Thumb
Synonyms
ValueSource
1,2-Dipalmitoyl-3-sn-phosphatidic acidChEBI
1,2-Dipalmitoyl-sn-glycerol-3-phosphateChEBI
1,2-Dipalmitoyl-sn-glycerol-3-phosphoric acidChEBI
Dipalmitoyl phosphatidic acidChEBI
PA(32:0)ChEBI
Phosphatidic acid(16:0/16:0)ChEBI
Phosphatidic acid(32:0)ChEBI
1,2-Dipalmitoyl-3-sn-phosphatidateGenerator
Dipalmitoyl phosphatidateGenerator
Phosphatidate(16:0/16:0)Generator
Phosphatidate(32:0)Generator
1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphorateHMDB
1,2-Di-O-palmitoyl-3-sn-glyceryl-O-phosphoric acidHMDB
1,2-Dihexadecanoyl-rac-phosphatidic acidHMDB
1,2-Dipalmitoyl-sn-glycerol 3-phosphateHMDB
1,2-Dipalmitoyl-sn-glycerol-3-phosphorateHMDB
Dipalmitoyl-L-a-phosphatidateHMDB
Dipalmitoyl-L-a-phosphatidic acidHMDB
Dipalmitoyl-L-alpha-phosphatidateHMDB
Dipalmitoyl-L-alpha-phosphatidic acidHMDB
DipalmitoylphosphatidateHMDB
Dipalmitoylphosphatidic acidHMDB
L-a-Dipalmitoyl-phosphatidateHMDB
L-a-Dipalmitoyl-phosphatidic acidHMDB
L-a-DipalmitoylphosphatidateHMDB
L-a-Dipalmitoylphosphatidic acidHMDB
L-alpha-Dipalmitoyl-phosphatidateHMDB
L-alpha-Dipalmitoyl-phosphatidic acidHMDB
L-alpha-DipalmitoylphosphatidateHMDB
L-alpha-Dipalmitoylphosphatidic acidHMDB
Dipalmitoylphosphatidic acid, calcium saltMeSH
Dipalmitoylphosphatidic acid, ammonium saltMeSH
1,2-Dipalmitoyl-sn-glycero-3-phosphateMeSH
Dipalmitoylphosphatidic acid, sodium saltMeSH
Dipalmitoylphosphatidic acid, (+-)-isomerMeSH
Dipalmitoylphosphatidic acid, (R)-isomerMeSH
Chemical FormulaC35H69O8P
Average Molecular Weight648.903
Monoisotopic Molecular Weight648.47300618
IUPAC Name[(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphonic acid
Traditional Namedipalmitoyl
CAS Registry Number7091-44-3
SMILES
[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC
InChI Identifier
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
InChI KeyPORPENFLTBBHSG-MGBGTMOVSA-N
Chemical 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent1,2-diacylglycerol-3-phosphates
Alternative Parents
Substituents
  • 1,2-diacylglycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point161 - 165 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00012 g/LALOGPS
logP8.66ALOGPS
logP11.88ChemAxon
logS-6.7ALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-6.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area119.36 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity178.57 m³·mol⁻¹ChemAxon
Polarizability80.09 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9236341000-d0296e5b3dd53599a39dView in MoNA
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, Positivesplash10-000i-0000900000-42187062de8aa3a7fcefView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a71-4092103000-08a70ad05021be172e3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-dc7f569f98cd450257d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f628227e9a0ceffbeaf0View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue LocationNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.186 +/- 0.037 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022175
KNApSAcK IDNot Available
Chemspider ID393518
KEGG Compound IDC00416
BioCyc IDCPD0-1422
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5644
PubChem Compound446066
PDB IDLPP
ChEBI ID73246
References
Synthesis ReferenceAndo, 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)
General References
  1. Niedernberg A, Tunaru S, Blaukat A, Ardati A, Kostenis E: Sphingosine 1-phosphate and dioleoylphosphatidic acid are low affinity agonists for the orphan receptor GPR63. Cell Signal. 2003 Apr;15(4):435-46. [PubMed:12618218 ]
  2. 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 ]

Only showing the first 10 proteins. There are 61 proteins in total.

Enzymes

General function:
Involved in protein binding
Specific function:
May have a role in signal-induced cytoskeletal regulation and/or endocytosis (By similarity).
Gene Name:
PLD2
Uniprot ID:
O14939
Molecular weight:
104656.485
General function:
Involved in diacylglycerol kinase activity
Specific function:
Phosphorylates diacylglycerol (DAG) to generate phosphatidic acid (PA). May regulate the activity of protein kinase C by controlling the balance between these two signaling lipids. Activated in the nucleus in response to alpha-thrombin and nerve growth factor. May be involved in cAMP- induced activation of NR5A1 and subsequent steroidogenic gene transcription by delivering PA as ligand for NR5A1. Acts synergistically with NR5A1 on CYP17 transcriptional activity
Gene Name:
DGKQ
Uniprot ID:
P52824
Molecular weight:
101154.0
General function:
Involved in diacylglycerol kinase activity
Specific function:
Reverses the normal flow of glycerolipid biosynthesis by phosphorylating diacylglycerol back to phosphatidic acid
Gene Name:
DGKG
Uniprot ID:
P49619
Molecular weight:
89095.3
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is PA > C-1-P > LPA > S-1-P.
Gene Name:
PPAP2C
Uniprot ID:
O43688
Molecular weight:
32573.435
General function:
Involved in diacylglycerol kinase activity
Specific function:
Upon cell stimulation converts the second messenger diacylglycerol into phosphatidate, initiating the resynthesis of phosphatidylinositols and attenuating protein kinase C activity
Gene Name:
DGKA
Uniprot ID:
P23743
Molecular weight:
82629.5
General function:
Involved in diacylglycerol kinase activity
Specific function:
Isoform 2 may be involved in cell growth and tumorigenesis. Involved in clathrin-dependent endocytosis
Gene Name:
DGKD
Uniprot ID:
Q16760
Molecular weight:
134524.2
General function:
Involved in catalytic activity
Specific function:
Broad-specificity phosphohydrolase that dephosphorylates exogenous bioactive glycerolipids and sphingolipids. Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). Pivotal regulator of lysophosphatidic acid (LPA) signaling in the cardiovascular system. Major enzyme responsible of dephosphorylating LPA in platelets, which terminates signaling actions of LPA. May control circulating, and possibly also regulate localized, LPA levels resulting from platelet activation. It has little activity towards ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA > PA > S-1-P > C-1-P. It's down-regulation may contribute to the development of colon adenocarcinoma.
Gene Name:
PPAP2A
Uniprot ID:
O14494
Molecular weight:
32155.715
General function:
Involved in diacylglycerol kinase activity
Specific function:
Exhibits high phosphorylation activity for long-chain diacylglycerols
Gene Name:
DGKB
Uniprot ID:
Q9Y6T7
Molecular weight:
90594.7
General function:
Involved in diacylglycerol kinase activity
Specific function:
ATP + 1,2-diacylglycerol = ADP + 1,2-diacyl- sn-glycerol 3-phosphate
Gene Name:
DGKI
Uniprot ID:
O75912
Molecular weight:
116996.2
General function:
Involved in catalytic activity
Specific function:
Catalyzes the conversion of phosphatidic acid (PA) to diacylglycerol (DG). In addition it hydrolyzes lysophosphatidic acid (LPA), ceramide-1-phosphate (C-1-P) and sphingosine-1-phosphate (S-1-P). The relative catalytic efficiency is LPA = PA > C-1-P > S-1-P. May be involved in cell adhesion and in cell-cell interactions.
Gene Name:
PPAP2B
Uniprot ID:
O14495
Molecular weight:
35115.61

Only showing the first 10 proteins. There are 61 proteins in total.