P. aeruginosa Metabolome Database: 1-hexadecanoyl-sn-glycerol 3-phosphate (PAMDB001538)

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

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 12:54:54 PM

Metabolite ID

PAMDB001538

Identification

Name:

1-hexadecanoyl-sn-glycerol 3-phosphate

Description:

1-hexadecanoyl-sn-glycerol 3-phosphate belongs to the class of Lysophosphatidic Acids. These are glycerophosphates where the glycerol is esterified with one saturated fatty acid. (inferred from compound structure)

Structure

🔍MOL SDF PDB SMILES InChI View Structure

Synonyms:

(2-hydroxy-3-phosphonooxypropyl) hexadecanoate
(2-Hydroxy-3-phosphonooxypropyl) hexadecanoic acid
1-Hexadecanoyl-sn-glycero-3-phosphate
1-Hexadecanoyl-sn-glycero-3-phosphoric acid
1-Hexadecanoyl-sn-glycerol 3-phosphoric acid
1-Palmitoyl lysophosphatidate
1-Palmitoyl lysophosphatidic acid
1-Palmitoylglycerol 3-phosphate
1-Palmitoylglycerol 3-phosphoric acid

Chemical Formula:

C₁₉H₃₉O₇P

Average Molecular Weight:

410.4825

Monoisotopic Molecular Weight:

410.243340114

InChI Key:

YNDYKPRNFWPPFU-UHFFFAOYSA-N

InChI:

InChI=1S/C19H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)25-16-18(20)17-26-27(22,23)24/h18,20H,2-17H2,1H3,(H2,22,23,24)

CAS number:

Not Available

IUPAC Name:

[3-(hexadecanoyloxy)-2-hydroxypropoxy]phosphonic acid

Traditional IUPAC Name:

PLPA

SMILES:

CCCCCCCCCCCCCCCC(=O)OCC(O)COP(O)(O)=O

Chemical Taxonomy

Taxonomy Description

This compound belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1-acylglycerol-3-phosphates

Alternative Parents

Substituents

1-acylglycerol-3-phosphate
Fatty acid ester
Monoalkyl phosphate
Organic phosphate
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Fatty acyl
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Alcohol
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Monoacylglycerophosphates (C04036 )

Physical Properties

State:

Not Available

Charge:

-2

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.00242 mg/mL	ALOGPS
logP	3.87	ALOGPS
logP	4.96	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	104.98 m³·mol^-1	ChemAxon
Polarizability	47.18 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	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:

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-08fr-2986700000-f3b30f5c39843042fd11	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4s-3942000000-0e96d3c410d5f67cbc44	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4s-6930000000-8e619c799b8a218b3a05	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4r-4190300000-bb83e3f01055cbe6102f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-9050000000-de299cedb3cf89da4492	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-f3fc94f808e80bf00353	View in MoNA

References

References:

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:

Not Available

Material Safety Data Sheet (MSDS)

Not Available

Links

External Links:

Resource	Link
CHEBI ID	64023
HMDB ID	Not Available
Pubchem Compound ID	89566
Kegg ID	C04036
ChemSpider ID	80836
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

• Glycerol-3-phosphate acyltransferase

General function:: Involved in transferase activity, transferring acyl groups
Specific function:: Catalyzes the transfer of an acyl group from acyl-ACP to glycerol-3-phosphate (G3P) to form lysophosphatidic acid (LPA). This enzyme can utilize either acyl-CoA or acyl-ACP as the fatty acyl donor
Gene Name:: plsB
Locus Tag:: PA3673
Molecular weight:: 94.8 kDa

Reactions

Acyl-CoA + sn-glycerol 3-phosphate = CoA + 1-acyl-sn-glycerol 3-phosphate.

Protein Details

• Acyl-CoA thioesterase I

General function:: Involved in hydrolase activity
Specific function:: Hydrolyzes only long chain acyl thioesters (C12-C18). Specificity similar to chymotrypsin
Gene Name:: tesA
Locus Tag:: PA2856
Molecular weight:: 21 kDa

Reactions

2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate.

Protein Details

• Acyl carrier protein

General function:: Involved in fatty acid biosynthetic process
Specific function:: Carrier of the growing fatty acid chain in fatty acid biosynthesis
Gene Name:: acpP
Locus Tag:: PA2966
Molecular weight:: 8.7 kDa

1-hexadecanoyl-sn-glycerol 3-phosphate (PAMDB001538)

Structure for 1-hexadecanoyl-sn-glycerol 3-phosphate (PAMDB001538)

Enzymes

Reactions

Reactions