Record Information
Version1.0
Creation date2015-10-09 22:30:45 UTC
Update date2017-01-19 02:36:24 UTC
FoodComEx IDPC000442
FoodDB RecordFDB022175
Chemical Information
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). [HMDB]
CAS Number7091-44-3
Structure
Thumb
Synonyms
SynonymSource
1,2-Di-O-palmitoyl-3-sn-glyceryl-O-orateHMDB
1,2-Di-O-palmitoyl-3-sn-glyceryl-O-oric acidHMDB
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-atidic acidHMDB
1,2-dihexadecanoyl-rac-phosphatidic acidhmdb
1,2-Dipalmitoyl-3-sn-atidateGenerator
1,2-Dipalmitoyl-3-sn-atidic acidChEBI
1,2-Dipalmitoyl-3-sn-phosphatidatehmdb
1,2-Dipalmitoyl-3-sn-phosphatidic acidhmdb
1,2-Dipalmitoyl-sn-glycerol 3-ateHMDB
1,2-Dipalmitoyl-sn-glycerol 3-phosphatehmdb
1,2-Dipalmitoyl-sn-glycerol-3-ateChEBI
1,2-Dipalmitoyl-sn-glycerol-3-ic acidGenerator
1,2-Dipalmitoyl-sn-glycerol-3-orateGenerator
1,2-Dipalmitoyl-sn-glycerol-3-oric acidChEBI
1,2-Dipalmitoyl-sn-glycerol-3-phosphoratehmdb
1,2-Dipalmitoyl-sn-glycerol-3-phosphoric acidhmdb
Atidate(16:0/16:0)Generator
Atidate(32:0)Generator
Atidic acid(16:0/16:0)ChEBI
Atidic acid(32:0)ChEBI
Dipalmitoyl atidateGenerator
Dipalmitoyl atidic acidChEBI
Dipalmitoyl-L-a-atidateHMDB
Dipalmitoyl-L-a-atidic acidHMDB
Dipalmitoyl-L-a-phosphatidatehmdb
Dipalmitoyl-L-a-phosphatidic acidhmdb
Dipalmitoyl-L-alpha-atidateHMDB
Dipalmitoyl-L-alpha-atidic acidHMDB
Dipalmitoyl-L-alpha-phosphatidatehmdb
Dipalmitoyl-L-alpha-phosphatidic acidhmdb
DipalmitoylatidateHMDB
Dipalmitoylatidic acidHMDB
Dipalmitoylphosphatidatehmdb
Dipalmitoylphosphatidic acidhmdb
L-a-Dipalmitoyl-atidateHMDB
L-a-Dipalmitoyl-atidic acidHMDB
L-a-Dipalmitoyl-phosphatidatehmdb
L-a-Dipalmitoyl-phosphatidic acidhmdb
L-a-DipalmitoylatidateHMDB
L-a-Dipalmitoylatidic acidHMDB
L-a-Dipalmitoylphosphatidatehmdb
L-a-Dipalmitoylphosphatidic acidhmdb
L-alpha-Dipalmitoyl-atidateHMDB
L-alpha-Dipalmitoyl-atidic acidHMDB
L-alpha-Dipalmitoyl-phosphatidatehmdb
L-alpha-Dipalmitoyl-phosphatidic acidhmdb
L-alpha-DipalmitoylatidateHMDB
L-alpha-Dipalmitoylatidic acidHMDB
L-alpha-Dipalmitoylphosphatidatehmdb
L-alpha-Dipalmitoylphosphatidic acidhmdb
PA(32:0)hmdb
Phosphatidic acid(16:0/16:0)hmdb
Phosphatidic acid(32:0)hmdb
Chemical FormulaNot Available
IUPAC nameNot Available
InChI IdentifierInChI=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
Isomeric SMILES[H][C@@](COC(=O)CCCCCCCCCCCCCCC)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC
Average Molecular Weight648.903
Monoisotopic Molecular Weight648.47300618
Chemical Taxonomy
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 Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 200 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Not Available