P. aeruginosa Metabolome Database: PA(16:0/16:0) (PAMDB000169)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB000169

Identification

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).

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

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

InChI Key:

PORPENFLTBBHSG-MGBGTMOVSA-N

InChI:

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

CAS number:

7091-44-3

IUPAC Name:

[(2R)-2,3-bis(hexadecanoyloxy)propoxy]phosphonic acid

Traditional IUPAC Name:

dipalmitoyl

SMILES:

CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC

Chemical Taxonomy

Taxonomy Description

This 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 Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1,2-diacylglycerol-3-phosphates

Alternative Parents

Substituents

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

1-acyl-2-hexadecanoyl-sn-glycero-3-phosphate (CHEBI:73246 )
Diacylglycerophosphates (LMGP10010027 )

Physical Properties

State:

Solid

Charge:

-2

Melting point:

161-165 °C

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.000118 mg/mL	ALOGPS
logP	8.66	ALOGPS
logP	11.88	ChemAxon
logS	-6.7	ALOGPS
pKa (Strongest Acidic)	1.32	ChemAxon
pKa (Strongest Basic)	-6.7	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	36	ChemAxon
Refractivity	178.57 m³·mol^-1	ChemAxon
Polarizability	80.09 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations:

Membrane

Reactions:

Cytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-didodecanoylglycerol + Pyrophosphate
Cytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-dihexadec-9-enoylglycerol + Pyrophosphate
Cytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-dihexadecanoylglycerol + Pyrophosphate
Cytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-dioctadec-11-enoylglycerol + Pyrophosphate
Cytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-Dioctadecanoylglycerol + Pyrophosphate
Cytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-ditetradec-7-enoylglycerol + Pyrophosphate
Cytidine triphosphate + Hydrogen ion + PA(16:0/16:0) > CDP-1,2-ditetradecanoylglycerol + Pyrophosphate
Adenosine triphosphate + Water + PA(16:0/16:0) > ADP + Hydrogen ion + Phosphate + PA(16:0/16:0)
Adenosine triphosphate + Water + PA(16:0/16:0) > ADP + Hydrogen ion + Phosphate + PA(16:0/16:0)
-->-->-->-->-->-->-->-->-->-->-->-->Water + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (didodecanoyl, n-C12:0) + Phosphate
Water + PA(16:0/16:0) > 1,2-Diacyl-sn-glycerol (dihexadec-9-enoyl, n-C16:1) + Phosphate

More...

Pathways:

Glycerolipid metabolism pae00561
Glycerophospholipid metabolism pae00564
Metabolic pathways pae01100

Spectra

Spectra:

Spectrum Type	Description	Splash Key
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0002-0000009000-b3b708036c56c15fec89	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0a4i-1492100000-5624ed03f664b67f79ec	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0a4i-1490000000-1ba8a217ef22599ee07c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
1D NMR	1H NMR Spectrum	Not Available
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available

References

References:

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. M.sc. 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)

Links

External Links:

Resource	Link
CHEBI ID	73246
HMDB ID	HMDB00674
Pubchem Compound ID	446066
Kegg ID	C00416
ChemSpider ID	393518
Wikipedia ID	Not Available
BioCyc ID	L-PHOSPHATIDATE
EcoCyc ID	L-PHOSPHATIDATE
Ligand Expo	PX6

Enzymes

Protein Details

• Phosphatidate cytidylyltransferase

General function:: Involved in transferase activity, transferring phosphorus-containing groups
Specific function:: CTP + phosphatidate = diphosphate + CDP- diacylglycerol
Gene Name:: cdsA
Locus Tag:: PA3651
Molecular weight:: 28.9 kDa

Reactions

CTP + phosphatidate = diphosphate + CDP-diacylglycerol.

Protein Details

• Diacylglycerol kinase

General function:: Involved in diacylglycerol kinase activity
Specific function:: Recycling of diacylglycerol produced during the turnover of membrane phospholipid
Gene Name:: dgkA
Locus Tag:: PA3603
Molecular weight:: 13.1 kDa

Reactions

ATP + 1,2-diacylglycerol = ADP + 1,2-diacyl-sn-glycerol 3-phosphate.

Protein Details

• Lipid A export ATP-binding/permease protein msbA

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:: msbA
Locus Tag:: PA4997
Molecular weight:: 66.4 kDa

Transporters

Protein Details

• Lipid A export ATP-binding/permease protein msbA

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:: msbA
Locus Tag:: PA4997
Molecular weight:: 66.4 kDa

Protein Details

• Probable phospholipid ABC transporter permease protein mlaE

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:: mlaE
Locus Tag:: PA4455
Molecular weight:: 28.4 kDa

PA(16:0/16:0) (PAMDB000169)

Structure for PA(16:0/16:0) (PAMDB000169)

Enzymes

Reactions

Reactions

Transporters