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Record Information

Version

2.0

Creation Date

2012-05-31 14:18:51 -0600

Update Date

2015-12-09 12:07:28 -0700

Secondary Accession Numbers

ECMDB10571

Identification

Name:

PG(16:0/16:1(9Z))

Description

PG(16:0/16:1(9Z)) 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(16:0/16:1(9Z)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 9Z-hexadecenoyl 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-Hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phospho-(1'-glycerol)
1-hexadecanoyl-2-(9Z-hexadecenoyl)-sn-glycero-3-phosphoglycerol
1-Palmitoyl-2-palmitoleoyl-sn-glycero-3-phosphoglycerol
1-phosphatidylglycerol
3(3-phosphatidyl-)glycerol
3-(3-sn-phosphatidyl)glycerol
3-(3-sn-Phosphatidyl)glycerol
GPG(16:0/16:1)
GPG(16:0/16:1n7)
GPG(16:0/16:1w7)
GPG(32:1)
PG(16:0/16:1)
PG(16:0/16:1n7)
PG(16:0/16:1w7)
PG(32:1)
Phosphatidylglycerol
Phosphatidylglycerol(16:0/16:1)
Phosphatidylglycerol(16:0/16:1n7)
Phosphatidylglycerol(16:0/16:1w7)
Phosphatidylglycerol(32:1)

Chemical Formula:

C₃₈H₇₃O₁₀P

Weight:

Average: 720.954
Monoisotopic: 720.494135068

InChI Key:

JZMVGKUGUWBISQ-BWTMDTOGSA-N

InChI:

InChI=1S/C38H73O10P/c1-3-5-7-9-11-13-15-17-19-21-23-25-27-29-37(41)45-33-36(34-47-49(43,44)46-32-35(40)31-39)48-38(42)30-28-26-24-22-20-18-16-14-12-10-8-6-4-2/h13,15,35-36,39-40H,3-12,14,16-34H2,1-2H3,(H,43,44)/b15-13-/t35-,36+/m0/s1

CAS number:

Not Available

IUPAC Name:

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

Traditional IUPAC Name:

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

SMILES:

[H][C@](O)(CO)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCC)OC(=O)CCCCCCCCCCCCCCC

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Diacylglycerophosphoglycerols (LMGP04010207 )

Physical Properties

State:

Solid

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.00014 g/L	ALOGPS
logP	7.73	ALOGPS
logP	10.58	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	39	ChemAxon
Refractivity	196.43 m³·mol⁻¹	ChemAxon
Polarizability	86.28 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:

Water + PGP(16:0/16:1(9Z)) > Phosphate + PG(16:0/16:1(9Z))
PG(16:0/16:1(9Z)) + PE(18:1(9Z)/18:1(9Z)) > CL(16:0/18:1(9Z)/18:1(9Z)/16:1(9Z)) + Ethanolamine
PE(19:iso/19:iso) + PG(16:0/16:1(9Z)) > CL(16:0/19:0cycv8c/19:0cycv8c/16:1(9Z)) + Ethanolamine
PE(17:0cycw7c/17:0cycw7c) + PG(16:0/16:1(9Z)) > Ethanolamine + CL(17:0cycw7c/16:0/17:0cycw7c/16:1(9Z))
PE(19:0cycv8c/19:iso) + PG(16:0/16:1(9Z)) > Ethanolamine + CL(19:0cycv8c/16:0/16:1(9Z)/19:0cycv8c)

SMPDB Pathways:

phospholipid biosynthesis (CL(19:0cycv8c/16:0/16:1(9Z)/19:0cycv8c))	PW001326
phospholipid biosynthesis CL(16:0/18:1(9Z)/18:1(9Z)/16:1(9Z))	PW001369
phospholipid biosynthesis CL(16:0/19:0cycv8c/19:0cycv8c/16:1(9Z))	PW001411
phospholipid biosynthesis CL(17:0cycw7c/16:0/17:0cycw7c/16:1(9Z))	PW001682

KEGG Pathways:

Glycerophospholipid metabolism ec00564

EcoCyc Pathways:

phospholipid biosynthesis I PHOSLIPSYN-PWY

Concentrations

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0gki-4290711700-b2d721820faf31ee367c	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00p1-6291411200-32a7732218a31f4ef3fe	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4j-9262221000-2efddd0bb231243ec526	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0uy0-0190401300-959059a275faa0c6b56e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ufr-5291100000-4e000d107fdd3f2a87a5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9020000000-75b24a6d47a55e02280e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000000900-dbc822615d212739308e	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-10k9-0091300400-7b0bf000719096af4470	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-10k9-0191300400-faaabd9809053c30be52	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
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
Uniprot Consortium (2012). "Reorganizing the protein space at the Universal Protein Resource (UniProt)." Nucleic Acids Res 40:D71-D75. Pubmed: 22102590
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	HMDB10571
Pubchem Compound ID	52926472
Kegg ID	C00344
ChemSpider ID	24768072
Wikipedia ID	Not Available
BioCyc ID	L-1-PHOSPHATIDYL-GLYCEROL
EcoCyc ID	L-1-PHOSPHATIDYL-GLYCEROL

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. 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

4. 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

5. 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

6. 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

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. 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

3. 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(16:0/16:1(9Z)) (M2MDB000792)

Structure for #<Compound:0xa91e392c>

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Transporters