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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2008-09-12 01:27:19 UTC
Update Date2018-05-19 22:09:27 UTC
HMDB IDHMDB0007860
Secondary Accession Numbers
  • HMDB07860
Metabolite Identification
Common NamePA(16:0/18:2(9Z,12Z))
DescriptionPA(16:0/18:2(9Z,12Z)) 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(16:0/18:2(9Z,12Z)), in particular, consists of one chain of palmitic acid at the C-1 position and one chain of linoleic acid at the C-2 position. The palmitic acid moiety is derived from fish oils, milk fats, vegetable oils and animal fats, while the linoleic acid moiety is derived from seed oils. 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
1-16:0-2-18:2-Phosphatidic acidChEBI
1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphateChEBI
16:0-18:2-PAChEBI
2-Linoleoyl-1-palmitoyl-sn-glycero-3-phosphateChEBI
PA(16:0/18:2)ChEBI
PA(16:0/18:2OMEGA6)ChEBI
PA(34:2)ChEBI
Phosphatidic acid(16:0/18:2)ChEBI
Phosphatidic acid(16:0/18:2omega6)ChEBI
Phosphatidic acid(34:2)ChEBI
1-16:0-2-18:2-PhosphatidateGenerator
1-Palmitoyl-2-linoleoyl-sn-glycero-3-phosphoric acidGenerator
2-Linoleoyl-1-palmitoyl-sn-glycero-3-phosphoric acidGenerator
Phosphatidate(16:0/18:2)Generator
Phosphatidate(16:0/18:2OMEGA6)Generator
Phosphatidate(34:2)Generator
1-Hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-phosphatidic acidHMDB
PA(16:0/18:2N6)HMDB
PA(16:0/18:2W6)HMDB
Phosphatidic acid(16:0/18:2n6)HMDB
Phosphatidic acid(16:0/18:2W6)HMDB
Chemical FormulaC37H69O8P
Average Molecular Weight672.9127
Monoisotopic Molecular Weight672.473005696
IUPAC Name[(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphonic acid
Traditional Name(2R)-3-(hexadecanoyloxy)-2-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)OC[C@]([H])(COP(O)(=O)O)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC
InChI Identifier
InChI=1S/C37H69O8P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-37(39)45-35(34-44-46(40,41)42)33-43-36(38)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h11,13,17-18,35H,3-10,12,14-16,19-34H2,1-2H3,(H2,40,41,42)/b13-11-,18-17-/t35-/m1/s1
InChI KeyYQMUIZXKIKXZHD-UMKNCJEQSA-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 PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility8.0e-05 g/LALOGPS
logP8.78ALOGPS
logP12.04ChemAxon
logS-6.9ALOGPS
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
Refractivity190.01 m³·mol⁻¹ChemAxon
Polarizability81.34 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, Positivesplash10-01ot-9472312000-5a0ace43ce559faf6b1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-022l-0192214000-0ff5badab9b87707949eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01p2-1292111000-4a699460a7645a5a2ac2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03ds-0392011000-a011b8cc1a3b8c4d40a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05dr-3091102000-a4a318dd2dd7912c0151View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9060000000-f674e5442d2d2e19904cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9010000000-be58bb50c1230574e53cView in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
Tissue Location
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.144 +/- 0.015 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 IDFDB025052
KNApSAcK IDNot Available
Chemspider ID7826110
KEGG Compound IDC00416
BioCyc IDCPD-8265
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9547167
PDB IDNot Available
ChEBI ID73259
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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 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 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
General function:
Involved in ATP binding
Specific function:
May play a role in the transport of aminophospholipids from the outer to the inner leaflet of various membranes and the maintenance of asymmetric distribution of phospholipids in the canicular membrane. May have a role in transport of bile acids into the canaliculus, uptake of bile acids from intestinal contents into intestinal mucosa or both
Gene Name:
ATP8B1
Uniprot ID:
O43520
Molecular weight:
143694.1
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 ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP10A
Uniprot ID:
O60312
Molecular weight:
167686.6
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP8B3
Uniprot ID:
O60423
Molecular weight:
146750.9
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP9A
Uniprot ID:
O75110
Molecular weight:
118581.5
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP10B
Uniprot ID:
O94823
Molecular weight:
165388.9
General function:
Involved in lipid binding
Specific function:
Converts HDL into larger and smaller particles. May play a key role in extracellular phospholipid transport and modulation of hdl particles
Gene Name:
PLTP
Uniprot ID:
P55058
Molecular weight:
54738.8
General function:
Involved in ATP binding
Specific function:
ATP + H(2)O + phospholipid(In) = ADP + phosphate + phospholipid(Out)
Gene Name:
ATP11A
Uniprot ID:
P98196
Molecular weight:
129754.6

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