Record Information
Version1.0
Creation date2011-09-21 00:52:12 UTC
Update date2020-04-06 23:43:34 UTC
Primary IDFDB025052
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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). [HMDB]
CAS NumberNot Available
Structure
Thumb
Synonyms
SynonymSource
1-16:0-2-18:2-AtidateGenerator
1-16:0-2-18:2-Atidic acidChEBI
1-Hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-atidic acidHMDB
1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-phosphatidic acidhmdb
1-Palmitoyl-2-linoleoyl-sn-glycero-3-ateChEBI
1-Palmitoyl-2-linoleoyl-sn-glycero-3-ic acidGenerator
1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphatehmdb
16:0-18:2-PAChEBI
2-Linoleoyl-1-palmitoyl-sn-glycero-3-ateChEBI
2-Linoleoyl-1-palmitoyl-sn-glycero-3-ic acidGenerator
Atidate(16:0/18:2)Generator
Atidate(16:0/18:2omega6)Generator
Atidate(34:2)Generator
Atidic acid(16:0/18:2)ChEBI
Atidic acid(16:0/18:2N6)HMDB
Atidic acid(16:0/18:2omega6)ChEBI
Atidic acid(16:0/18:2W6)HMDB
Atidic acid(34:2)ChEBI
PA(16:0/18:2)hmdb
PA(16:0/18:2n6)hmdb
PA(16:0/18:2omega6)ChEBI
PA(16:0/18:2w6)hmdb
PA(34:2)hmdb
Phosphatidic acid(16:0/18:2)hmdb
Phosphatidic acid(16:0/18:2n6)hmdb
Phosphatidic acid(16:0/18:2w6)hmdb
Phosphatidic acid(34:2)hmdb
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
Polarizability80.96 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC37H69O8P
IUPAC name[(2R)-3-(hexadecanoyloxy)-2-(octadeca-9,12-dienoyloxy)propoxy]phosphonic acid
InChI IdentifierInChI=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)/t35-/m1/s1
InChI KeyYQMUIZXKIKXZHD-PGUFJCEWSA-N
Isomeric SMILES[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCC=CCC=CCCCCC
Average Molecular Weight672.9127
Monoisotopic Molecular Weight672.473005696
Classification
Description 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 DescriptorsNot Available
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
ChemSpider ID7826110
ChEMBL IDNot Available
KEGG Compound IDC00416
Pubchem Compound ID9547167
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB07860
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDLecithin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
2-acylglycerol O-acyltransferase 2MOGAT2Q3SYC2
Phospholipase D2PLD2O14939
Phosphatidate cytidylyltransferase 2CDS2O95674
Lipid phosphate phosphatase-related protein type 4LPPR4Q7Z2D5
Phosphatidate phosphatase PPAPDC1APPAPDC1AQ5VZY2
Phosphatidate phosphatase PPAPDC1BPPAPDC1BQ8NEB5
Phosphatidylinositol-glycan-specific phospholipase DGPLD1P80108
Diacylglycerol kinase, epsilon 64kDaDGKEA1L4Q0
Phospholipase DDHD1DDHD1Q8NEL9
1-acyl-sn-glycerol-3-phosphate acyltransferase gammaAGPAT3Q9NRZ7
1-acyl-sn-glycerol-3-phosphate acyltransferase betaAGPAT2O15120
1-acyl-sn-glycerol-3-phosphate acyltransferase alphaAGPAT1Q99943
1-acyl-sn-glycerol-3-phosphate acyltransferase epsilonAGPAT5Q9NUQ2
1-acyl-sn-glycerol-3-phosphate acyltransferase deltaAGPAT4Q9NRZ5
Lysocardiolipin acyltransferase 1LCLAT1Q6UWP7
Lipid phosphate phosphatase-related protein type 5LPPR5Q32ZL2
Presqualene diphosphate phosphatasePPAPDC2Q8IY26
Probable lipid phosphate phosphatase PPAPDC3PPAPDC3Q8NBV4
Phospholipase DDHD2DDHD2O94830
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference