ECMDB: PG(15:0/16:1) (ECMDB21636) (M2MDB002030)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (5)XML

Proteins (5)

Record Information

Version

2.0

Creation Date

2012-08-13 14:57:53 -0600

Update Date

2015-06-03 17:21:59 -0600

Secondary Accession Numbers

ECMDB21636

Identification

Name:

PG(15:0/16:1)

Description

PG(15:0/16:1) is a phosphatidylglycerol or glycerophospholipid (PG or GP). It is a glycerophospholipid in which a phosphoglycerol moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylglycerols 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. PG(15:0/16:1), in particular, consists of one chain of pentadecanoic acid at the C-1 position and one chain of palmitoleic acid at the C-2 position. Phosphatidylglycerol is formed from phosphatidic acid by a sequence of enzymatic reactions that proceeds via the intermediate, cytidine diphosphate diacylglycerol (CDP-diacylglycerol). Bioynthesis proceeds by condensation of phosphatidic acid and cytidine triphosphate with elimination of pyrophosphate via the action of phosphatidate cytidyltransferase (or CDP-synthase). CDP-diacylglycerol then reacts with glycerol-3-phosphate via phosphatidylglycerophosphate synthase to form 3-sn-phosphatidyl-1'-sn-glycerol 3'-phosphoric acid, with the release of cytidine monophosphate (CMP). Finally, phosphatidylglycerol is formed by the action of specific phosphatases. PG also serves as a precursor for the synthesis of cardiolipin. PG is synthesized from CDP-diacylglycerol and glycerol-3-phosphate.

Structure

MOL SDF PDB SMILES InChI

Synonyms:

1-pentadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phospho-(1'-glycerol)
1-pentadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphoglycerol
1-pentadecanoyl-2-animal fats and vegetable oils-sn-glycero-3-phospho-(1'-glycerol)
1-pentadecanoyl-2-animal fats and vegetable oils-sn-glycero-3-phosphoglycerol
1-pentadecanoyl-2-palmitoleoyl-sn-glycero-3-phosphoglycerol
GPG(15:0/16:1)
GPG(31:1)
PG(31:1)
Phosphatidylglycerol(15:0/16:1)
Phosphatidylglycerol(31:1)

Chemical Formula:

C₃₇H₇₁O₁₀P

Weight:

Average: 706.9274
Monoisotopic: 706.478485004

InChI Key:

XINYTKIWPKLZAT-SQFISAMPSA-N

InChI:

InChI=1S/C37H71O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-37(41)47-35(33-46-48(42,43)45-31-34(39)30-38)32-44-36(40)28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13,15,34-35,38-39H,3-12,14,16-33H2,1-2H3,(H,42,43)/b15-13-

CAS number:

Not Available

IUPAC Name:

(2,3-dihydroxypropoxy)({2-[(9Z)-hexadec-9-enoyloxy]-3-(pentadecanoyloxy)propoxy})phosphinic acid

Traditional IUPAC Name:

2,3-dihydroxypropoxy(2-[(9Z)-hexadec-9-enoyloxy]-3-(pentadecanoyloxy)propoxy)phosphinic acid

SMILES:

CCCCCCCCCCCCCCC(=O)OCC(COP(O)(=O)OCC(O)CO)OC(=O)CCCCCCC\C=C/CCCCCC

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. 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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoglycerols

Direct Parent

Phosphatidylglycerols

Alternative Parents

Substituents

1,2-diacylglycerophosphoglycerol
Dialkyl phosphate
Fatty acid ester
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Dicarboxylic acid or derivatives
Secondary alcohol
Carboxylic acid ester
1,2-diol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	0.00016 g/L	ALOGPS
logP	7.48	ALOGPS
logP	10.13	ChemAxon
logS	-6.7	ALOGPS
pKa (Strongest Acidic)	1.89	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	148.82 Å²	ChemAxon
Rotatable Bond Count	38	ChemAxon
Refractivity	191.82 m³·mol⁻¹	ChemAxon
Polarizability	84.74 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:

More...

SMPDB Pathways:

phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/15:0cyclo/18:1(9Z))	PW001064
phospholipid biosynthesis (CL(15:0cyclo/15:0cyclo/15:0cyclo/15:0cyclo))	PW002015
phospholipid biosynthesis (CL(15:0cyclo/15:0cyclo/18:1(9Z)/16:0))	PW001713
phospholipid biosynthesis (CL(15:0cyclo/16:0/19:0cycv8c/15:0cyclo))	PW001114
phospholipid biosynthesis (CL(19:0cycv8c/15:0cyclo/19:0cycv8c/16:1(9Z)))	PW001317
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/14:0/16:0)	PW001059
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/14:0/16:1(9Z))	PW001060
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/14:0/18:1(9Z))	PW001061
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/16:0/14:0)	PW001066
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/16:0/16:1(9Z))	PW001063
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/16:0/17:0cycw7c)	PW001067
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/16:0/18:1(9Z))	PW001069
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/16:0/19:0cycv8c)	PW001070
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/16:1(9Z)/14:0)	PW001071
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/16:1(9Z)/16:0)	PW001072
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/16:1(9Z)/17:0cycw7c)	PW001073
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/16:1(9Z)/18:1(9Z))	PW001074
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/16:1(9Z)/19:0cycv8c)	PW001075
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/17:0cycw7c/16:0)	PW001076
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/17:0cycw7c/16:1(9Z))	PW001077
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/18:1(9Z)/16:1(9Z))	PW001083
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/19:0cycv8c/16:0)	PW001089
phospholipid biosynthesis CL(15:0cyclo/15:0cyclo/19:0cycv8c/16:1(9Z))	PW001090
phospholipid biosynthesis CL(15:0cyclo/16:0/14:0/15:0cyclo)	PW001094
phospholipid biosynthesis CL(15:0cyclo/16:0/15:0cyclo/14:0)	PW001095
phospholipid biosynthesis CL(15:0cyclo/16:0/15:0cyclo/16:1(9Z))	PW001096
phospholipid biosynthesis CL(15:0cyclo/16:0/15:0cyclo/17:0cycw7c)	PW001097
phospholipid biosynthesis CL(15:0cyclo/16:0/15:0cyclo/18:1(9Z))	PW001098
phospholipid biosynthesis CL(15:0cyclo/16:0/15:0cyclo/19:0cycv8c)	PW001099
phospholipid biosynthesis CL(15:0cyclo/16:0/16:1(9Z)/15:0cyclo)	PW001107
phospholipid biosynthesis CL(15:0cyclo/16:0/17:0cycw7c/15:0cyclo)	PW001101
phospholipid biosynthesis CL(15:0cyclo/16:0/17:0cycw7c/17:0cycw7c)	PW001110
phospholipid biosynthesis CL(15:0cyclo/16:0/18:1(9Z)/15:0cyclo)	PW001111
phospholipid biosynthesis CL(15:0cyclo/16:0/19:0cycv8c/19:0cycv8c)	PW001116
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/14:0/15:0cyclo)	PW001117
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/15:0cyclo/14:0)	PW001119
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/15:0cyclo/17:0cycw7c)	PW001121
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/15:0cyclo/18:1(9Z))	PW001122
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/15:0cyclo/19:0cycv8c)	PW001123
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/17:0cycw7c/15:0cyclo)	PW001133
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/17:0cycw7c/17:0cycw7c)	PW001135
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/18:1(9Z)/15:0cyclo)	PW001136
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/19:0cycv8c/15:0cyclo)	PW001139
phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/19:0cycv8c/19:0cycv8c)	PW001141
phospholipid biosynthesis CL(15:0cyclo/17:0cycw7c/16:0/17:0cycw7c)	PW001146
phospholipid biosynthesis CL(15:0cyclo/17:0cycw7c/16:1(9Z)/17:0cycw7c)	PW001148
phospholipid biosynthesis CL(15:0cyclo/17:0cycw7c/17:0cycw7c)/16:0)	PW001151
phospholipid biosynthesis CL(15:0cyclo/17:0cycw7c/17:0cycw7c/16:1(9Z))	PW001152
phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/16:0/19:0cycv8c)	PW001190
phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/16:1(9Z)/19:0cycv8c)	PW001192
phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/19:0cycv8c/16:0)	PW001200
phospholipid biosynthesis CL(15:0cyclo/19:0cycv8c/19:0cycv8c/16:1(9Z))	PW001201
phospholipid biosynthesis CL(16:0/15:0cyclo/14:0/15:0cyclo)	PW001220
phospholipid biosynthesis CL(16:0/15:0cyclo/15:0cyclo/14:0)	PW001221
phospholipid biosynthesis CL(16:0/15:0cyclo/15:0cyclo/16:1(9Z))	PW001222
phospholipid biosynthesis CL(16:0/15:0cyclo/15:0cyclo/17:0cycw7c)	PW001223
phospholipid biosynthesis CL(16:0/15:0cyclo/15:0cyclo/18:1(9Z))	PW001224
phospholipid biosynthesis CL(16:0/15:0cyclo/15:0cyclo/19:0cycv8c)	PW001225
phospholipid biosynthesis CL(16:0/15:0cyclo/16:1(9Z)/15:0cyclo)	PW001231
phospholipid biosynthesis CL(16:0/15:0cyclo/17:0cycw7c/15:0cyclo)	PW001236
phospholipid biosynthesis CL(16:0/15:0cyclo/17:0cycw7c/17:0cycw7c)	PW001238
phospholipid biosynthesis CL(16:0/15:0cyclo/18:1(9Z)/15:0cyclo)	PW001239
phospholipid biosynthesis CL(16:0/15:0cyclo/19:0cycv8c/15:0cyclo)	PW001245
phospholipid biosynthesis CL(16:0/15:0cyclo/19:0cycv8c/19:0cycv8c)	PW001247
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/15:0cyclo/19:0cycv8c)	PW001442
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/17:0cycw7c/15:0cyclo)	PW001457
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/17:0cycw7c/17:0cycw7c)	PW001459
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/19:0cycv8c/15:0cyclo)	PW001463
phospholipid biosynthesis CL(16:1(9Z)/15:0cyclo/19:0cycv8c/19:0cycv8c)	PW001469
phospholipid biosynthesis CL(17:0cycw7c/15:0cyclo/16:0/17:0cycw7c)	PW001652
phospholipid biosynthesis CL(17:0cycw7c/15:0cyclo/16:1(9Z)/17:0cycw7c)	PW001653
phospholipid biosynthesis CL(17:0cycw7c/15:0cyclo/17:0cycw7c/16:0)	PW001656
phospholipid biosynthesis CL(17:0cycw7c/15:0cyclo/17:0cycw7c/16:1(9Z))	PW001657

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_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ukc-0190201100-66ce7828710ec1c34201	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0096-4391101000-9e150e0097254381cea4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9121000000-0e3b63270157e9cf1bd8	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0550-3190513200-d53017fd4cee86815b50	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004r-4290212000-a291d73d3b9395d71433	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a71-8391020000-5236713f3d8d78c3badd	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
Oursel, D., Loutelier-Bourhis, C., Orange, N., Chevalier, S., Norris, V., Lange, C. M. (2007). "Lipid composition of membranes of Escherichia coli by liquid chromatography/tandem mass spectrometry using negative electrospray ionization." Rapid Commun Mass Spectrom 21:1721-1728. Pubmed: 17477452
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	138296518
Kegg ID	Not Available
ChemSpider ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Enzymes

Protein Details

1. 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

2. 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

3. 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

4. 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.

Protein Details

5. Cardiolipin synthase C

General function:: cardiolipin biosynthetic process
Specific function:: Catalyzes the synthesis of cardiolipin (CL) (diphosphatidylglycerol) from phosphatidylglycerol (PG) and phosphatidylethanolamine (PE).
Gene Name:: clsC
Uniprot ID:: P75919
Molecular weight:: 53665

Reactions

Phosphatidylglycerol + phosphatidylethanolamine = diphosphatidylglycerol + ethanolamine

PG(15:0/16:1) (ECMDB21636) (M2MDB002030)

Structure for #<Compound:0xabbacb3c>

Enzymes

Reactions

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