ECMDB: 1-hexadecanoyl-sn-glycerol 3-phosphate (ECMDB21129) (M2MDB001538)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (6)XML

Proteins (6)

Record Information

Version

2.0

Creation Date

2012-07-30 14:54:40 -0600

Update Date

2015-06-03 17:20:42 -0600

Secondary Accession Numbers

ECMDB21129

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

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

Weight:

Average: 410.4825
Monoisotopic: 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

Description

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-lysophosphatidic acid (CHEBI:64023 )
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	0.0024 g/L	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:

SMPDB Pathways:

Not Available

KEGG Pathways:

Not Available

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-02n9-5940100000-a5ca92d33fddeb085287	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-03di-0549600000-25838221a69792238ab5	View in MoNA
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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0000900000-97431642e54a4a707394	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0000900000-97431642e54a4a707394	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-2951500000-d6189b2a977487b10d88	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0000900000-61bb60154e9d7308c06d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-0000900000-61bb60154e9d7308c06d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00du-0955100000-a47b051136d1c4973480	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	HMDB0007853
Pubchem Compound ID	89566
Kegg ID	C04036
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. 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
Uniprot ID:: P0A7A7
Molecular weight:: 91381

Reactions

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

Protein Details

2. Phospholipase A1

General function:: Involved in phospholipase activity
Specific function:: Has broad substrate specificity including hydrolysis of phosphatidylcholine with phospholipase A2 (EC 3.1.1.4) and phospholipase A1 (EC 3.1.1.32) activities. Strong expression leads to outer membrane breakdown and cell death; is dormant in normal growing cells. Required for efficient secretion of bacteriocins
Gene Name:: pldA
Uniprot ID:: P0A921
Molecular weight:: 33163

Reactions

Phosphatidylcholine + H(2)O = 2-acylglycerophosphocholine + a carboxylate.
Phosphatidylcholine + H(2)O = 1-acylglycerophosphocholine + a carboxylate.

Protein Details

3. 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
Uniprot ID:: P0ADA1
Molecular weight:: 23622

Reactions

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

Protein Details

4. 1-acyl-sn-glycerol-3-phosphate acyltransferase

General function:: Involved in transferase activity, transferring acyl groups
Specific function:: Converts lysophosphatidic acid (LPA) into phosphatidic acid by incorporating an acyl moiety at the 2 position. This enzyme can utilize either acyl-CoA or acyl-ACP as the fatty acyl donor
Gene Name:: plsC
Uniprot ID:: P26647
Molecular weight:: 27453

Reactions

Acyl-CoA + 1-acyl-sn-glycerol 3-phosphate = CoA + 1,2-diacyl-sn-glycerol 3-phosphate.
Acyl-[acyl-carrier-protein] + 1-acyl-sn-glycerol 3-phosphate = [acyl-carrier-protein] + 1,2-diacyl-sn-glycerol 3-phosphate.

Protein Details

5. Probable glycerol-3-phosphate acyltransferase

General function:: Involved in glycerol-3-phosphate O-acyltransferase acti
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 also utilize acyl-CoA as fatty acyl donor, but not acyl-PO(4) (Probable)
Gene Name:: plsY
Uniprot ID:: P60782
Molecular weight:: 22193

Reactions

Acyl-CoA + sn-glycerol 3-phosphate = CoA + 1-acyl-sn-glycerol 3-phosphate.
Acyl-[acyl-carrier-protein] + sn-glycerol 3-phosphate = [acyl-carrier-protein] + 1-acyl-sn-glycerol 3-phosphate.

Protein Details

6. 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
Uniprot ID:: P0A6A8
Molecular weight:: 8640

1-hexadecanoyl-sn-glycerol 3-phosphate (ECMDB21129) (M2MDB001538)

Structure for #<Compound:0x6dff81ac>

Enzymes

Reactions

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