ECMDB: PG(18:1(9Z)/16:1(9Z)) (ECMDB24135) (M2MDB006252)

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

Proteins (5)

Record Information

Version

2.0

Creation Date

2015-09-08 17:49:35 -0600

Update Date

2015-12-09 12:08:16 -0700

Secondary Accession Numbers

ECMDB24135

Identification

Name:

PG(18:1(9Z)/16:1(9Z))

Description

PG(18:1(9Z)/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(18:1(9Z)/16:1(9Z)), in particular, consists of one 9Z-octadecenoyl 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:

Value	Source
1-(9Z-Hexadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phospho-(1'-glycerol)	HMDB
1-Palmitoleoyl-2-oleoyl-sn-glycero-3-phosphoglycerol	HMDB
GPG(16:1/18:1)	HMDB
GPG(16:1N7/18:1N9)	HMDB
GPG(16:1W7/18:1W9)	HMDB
GPG(34:2)	HMDB
PG(16:1/18:1)	HMDB
PG(16:1N7/18:1N9)	HMDB
PG(16:1W7/18:1W9)	HMDB
PG(34:2)	HMDB
Phosphatidylglycerol(16:1/18:1)	HMDB
Phosphatidylglycerol(16:1n7/18:1n9)	HMDB
Phosphatidylglycerol(16:1W7/18:1W9)	HMDB
Phosphatidylglycerol(34:2)	HMDB
1-(9Z-Hexadecenoyl)-2-(9Z-octadecenoyl)-sn-glycero-3-phosphoglycerol	HMDB
PG(16:1(9Z)/18:1(9Z))	Lipid Annotator

Chemical Formula:

C₄₀H₇₅O₁₀P

Weight:

Average: 746.9913
Monoisotopic: 746.509785132

InChI Key:

VCYYBLIRAQBPTM-GDNUZSQHSA-N

InChI:

InChI=1S/C40H75O10P/c1-3-5-7-9-11-13-15-17-18-20-22-24-26-28-30-32-40(44)50-38(36-49-51(45,46)48-34-37(42)33-41)35-47-39(43)31-29-27-25-23-21-19-16-14-12-10-8-6-4-2/h14,16-18,37-38,41-42H,3-13,15,19-36H2,1-2H3,(H,45,46)/b16-14-,18-17-/t37-,38+/m0/s1

CAS number:

Not Available

IUPAC Name:

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

Traditional IUPAC Name:

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

SMILES:

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

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 (LMGP04010902 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.00011 g/L	ALOGPS
logP	8.02	ALOGPS
logP	11.1	ChemAxon
logS	-6.8	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	40	ChemAxon
Refractivity	206.74 m³·mol⁻¹	ChemAxon
Polarizability	88.95 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:

SMPDB Pathways:

phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/14:0/14:0))	PW001601
phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/14:0/16:1(9Z)))	PW001607
phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/14:0/18:1(9Z)))	PW001608
phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/16:1(9Z)/14:0))	PW001609
phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/16:1(9Z)/17:0cycw7c))	PW001610
phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/16:1(9Z)/19:0cycv8c))	PW001612
phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/17:0cycw7c/17:0cycw7c))	PW001618
phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/14:0))	PW001620
phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/16:1(9Z)))	PW001621
phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/17:0cycw7c))	PW002014
phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/18:1(9Z)))	PW001622
phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/18:1(9Z)/19:0cycv8c))	PW001623
phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/19:0cycv8c/18:1(9Z)))	PW001630
phospholipid biosynthesis (CL(18:1(9Z)/16:1(9Z)/19:0cycv8c/19:0cycv8c))	PW001632

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 (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	splash10-00or-3190510500-de4829295339d6ca2193	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00or-4291211100-8be3bc8f9c91debbb6e6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-8193121000-52c4d31c52074f074f63	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0uei-0190200200-0c8dce1897e49ffb18e4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ufr-4290100000-fc75d67775be7b08cbc4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9030100000-6d796ea45dad3f3899ad	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000000900-6a6a3edc7613adf01568	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0uf1-0090300400-d377ddb6dd8dfe25475a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0uf1-0190300400-5254bc3d1dcb8621b286	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	89093
HMDB ID	HMDB0010589
Pubchem Compound ID	52927167
Kegg ID	Not Available
ChemSpider ID	24768088
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(18:1(9Z)/16:1(9Z)) (ECMDB24135) (M2MDB006252)

Structure for #<Compound:0x9c8d60ac>

Enzymes

Reactions

Reactions

Reactions

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