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Record Information

Version

2.0

Creation Date

2012-10-24 09:54:57 -0600

Update Date

2015-12-09 12:06:34 -0700

Secondary Accession Numbers

ECMDB23665

Identification

Name:

PG(12:0/14:0(3-OH))

Description

PG(12:0/14:0(3-OH)) is a phosphatidylglycerol. Phosphatidylglycerols consist of a glycerol 3-phosphate backbone esterified to either saturated or unsaturated fatty acids on carbons 1 and 2. As is the case with diacylglycerols, phosphatidylglycerols can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PG(12:0/14:0(3-OH)), in particular, consists of one dodecanoyl chain to the C-1 atom, and one 3-hydroxytetradecanoyl to the C-2 atom. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

1-dodecanoyl-2-3-hydroxytetradecanoyl-sn-glycero-3-phospho-(1'-glycerol)
1-dodecanoyl-2-3-hydroxytetradecanoyl-sn-glycero-3-phosphoglycerol
1-dodecanoyl-2-3-hydroxytetradecanoyl-sn-glycero-3-phosphoglycerol
GPG(12:0/14:0)
GPG(26:0)
PG(12:0/14:0)
PG(26:0)
Phosphatidylglycerol(12:0/14:0)
Phosphatidylglycerol(26:0)

Chemical Formula:

C₃₂H₆₃O₁₁P

Weight:

Average: 654.819
Monoisotopic: 654.410799847

InChI Key:

DGHNMYOXHLFDJH-YHCMTOLSSA-N

InChI:

InChI=1S/C32H63O11P/c1-3-5-7-9-11-13-15-17-19-21-28(34)23-32(37)40-26-30(27-42-44(38,39)41-25-29(35)24-33)43-31(36)22-20-18-16-14-12-10-8-6-4-2/h28-30,33-35H,3-27H2,1-2H3,(H,38,39)/t28?,29-,30+/m0/s1

CAS number:

Not Available

IUPAC Name:

[(2S)-2,3-dihydroxypropoxy][(2R)-2-(dodecanoyloxy)-3-[(3-hydroxytetradecanoyl)oxy]propoxy]phosphinic acid

Traditional IUPAC Name:

(2S)-2,3-dihydroxypropoxy((2R)-2-(dodecanoyloxy)-3-[(3-hydroxytetradecanoyl)oxy]propoxy)phosphinic acid

SMILES:

[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CC(O)CCCCCCCCCCC)OC(=O)CCCCCCCCCCC

Chemical Taxonomy

Description

belongs to the class of organic compounds known as phosphatidylglycerols. These are glycerophosphoglycerols in which two fatty acids are bonded to the 1-glycerol moiety through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoglycerols

Direct Parent

Phosphatidylglycerols

Alternative Parents

Substituents

1,2-diacylglycerophosphoglycerol
Beta-hydroxy acid
Dialkyl phosphate
Fatty acid ester
Fatty acyl
Alkyl phosphate
Dicarboxylic acid or derivatives
Phosphoric acid ester
Organic phosphoric acid derivative
Hydroxy acid
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Primary alcohol
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Alcohol
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.001 g/L	ALOGPS
logP	5.14	ALOGPS
logP	7.04	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	1.89	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	169.05 Å²	ChemAxon
Rotatable Bond Count	34	ChemAxon
Refractivity	169.22 m³·mol⁻¹	ChemAxon
Polarizability	75.93 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:

2 PGP(12:0/14:0(3-OH)) + Water >2 PG(12:0/14:0(3-OH)) + Phosphate
2 PG(12:0/14:0(3-OH)) > Glycerol + CL(12:0/14:0(3-OH)/12:0/14:0(3-OH))

SMPDB Pathways:

phospholipid biosynthesis (CL(12:0/14:0(3-OH)/12:0/14:0(3-OH)))

PW001931

KEGG Pathways:

Glycerophospholipid metabolism ec00564

EcoCyc Pathways:

Not Available

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_3_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0550-3350809000-a2a01a5ccd62b213e959	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-8771915000-b20e6f52317c5da5c180	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a7i-9332420000-06c04650bcaaf73e82ea	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ufu-1690514000-43828a9ed8220c4ee8bb	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-6791110000-945c0abc2676a1ef1183	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9210000000-10a7dd648f56bd907f5e	View in MoNA
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	View in JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	View in JSpectraViewer

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
Yuan Y, Leeds JA, Meredith TC (2012). "Pseudomonas aeruginosa Directly Shunts β-Oxidation Degradation Intermediates into De Novo Fatty Acid Biosynthesis." J Bacteriol. 194(19):5185-96 Pubmed: 22753057
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	Not Available
HMDB ID	Not Available
Pubchem Compound ID	Not Available
Kegg ID	Not Available
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. Lysophospholipase L2

General function:: Lipid transport and metabolism
Specific function:: 2-lysophosphatidylcholine + H(2)O = glycerophosphocholine + a carboxylate
Gene Name:: pldB
Uniprot ID:: P07000
Molecular weight:: 38978

Reactions

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

Protein Details

2. Phosphatidylglycerophosphatase B

General function:: Involved in catalytic activity
Specific function:: Hydrolyzes phosphatidylglycerophosphate, phosphatidic acid, and lysophosphatidic acid; the pattern of activities varies according to subcellular location
Gene Name:: pgpB
Uniprot ID:: P0A924
Molecular weight:: 29021

Reactions

Phosphatidylglycerophosphate + H(2)O = phosphatidylglycerol + phosphate.

Protein Details

3. Phosphatidylglycerophosphatase A

General function:: Involved in phosphatidylglycerophosphatase activity
Specific function:: One of the three phospholipid phosphatases, specifically hydrolyzes phosphatidylglycerophosphate
Gene Name:: pgpA
Uniprot ID:: P18200
Molecular weight:: 19418

Reactions

Phosphatidylglycerophosphate + H(2)O = phosphatidylglycerol + phosphate.

Protein Details

4. 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
Uniprot ID:: P60752
Molecular weight:: 64460

Protein Details

5. Protein crcA

General function:: Not Available
Specific function:: Not known; overproduction leads to camphor resistance and chromosome condensation
Gene Name:: crcA
Uniprot ID:: P37001
Molecular weight:: 21770

Protein Details

6. Cardiolipin synthase

General function:: Involved in phosphotransferase activity, for other substituted phosphate groups
Specific function:: Catalyzes the reversible phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol. Affects resistance to the gyrase inhibitor novobiocin
Gene Name:: cls
Uniprot ID:: P0A6H8
Molecular weight:: 54822

Reactions

2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol.

Protein Details

7. Putative cardiolipin synthase ybhO

General function:: Involved in catalytic activity
Specific function:: Catalyzes, in vitro, the phosphatidyl group transfer from one phosphatidylglycerol molecule to another to form cardiolipin (CL) (diphosphatidylglycerol) and glycerol. Can also catalyze phosphatidyl group transfer to water to form phosphatidate. Catalyzes little, if any, cardiolipin synthesis in vivo, even when the expression level is very high
Gene Name:: ybhO
Uniprot ID:: P0AA84
Molecular weight:: 47633

Reactions

2 Phosphatidylglycerol = diphosphatidylglycerol + glycerol.

Transporters

Protein Details

1. Probable phospholipid ABC transporter-binding protein mlaB

General function:: Involved in phospholipid transporter activity
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:: mlaB
Uniprot ID:: P64602
Molecular weight:: 10680

Protein Details

2. 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
Uniprot ID:: P60752
Molecular weight:: 64460

Protein Details

3. Probable phospholipid ABC transporter-binding protein mlaD

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:: mlaD
Uniprot ID:: P64604
Molecular weight:: 19576

Protein Details

4. 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
Uniprot ID:: P64606
Molecular weight:: 27863

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PG(12:0/14:0(3-OH)) (M2MDB004055)

Structure for #<Compound:0xae9a7348>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Transporters