ECMDB: PG(16:0/18:1(9Z)) (ECMDB24132) (M2MDB006249)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes (3)XML

Proteins (3)

Record Information

Version

2.0

Creation Date

2015-09-08 17:49:34 -0600

Update Date

2015-12-09 12:07:30 -0700

Secondary Accession Numbers

ECMDB24132

Identification

Name:

PG(16:0/18:1(9Z))

Description

PG(16:0/18:1(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(16:0/18:1(9Z)), in particular, consists of one hexadecanoyl chain to the C-1 atom, and one 9Z-octadecenoyl 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-Oleoyl-2-palmitoyl-sn-glycero-3-phospho-(1'-sn-glycerol)	ChEBI
18:1/16:0 PG	ChEBI
2-Hexadecanoyl-1-[(9Z)-octadec-9-enoyl]-sn-glycero-3-phospho-(1'-sn-glycerol)	ChEBI
C18:1/16:0 PG	ChEBI
GPG(18:1/16:0)	ChEBI
GPG(18:1OMEGA9/16:0)	ChEBI
GPG(34:1)	ChEBI
PG(18:1/16:0)	ChEBI
PG(18:1OMEGA9/16:0)	ChEBI
PG(34:1)	ChEBI
Phosphatidylglycerol(18:1/16:0)	ChEBI
Phosphatidylglycerol(18:1omega9/16:0)	ChEBI
Phosphatidylglycerol(34:1)	ChEBI
1-(9Z-Octadecenoyl)-2-hexadecanoyl-sn-glycero-3-phospho-(1'-glycerol)	HMDB
1-Oleoyl-2-palmitoyl-sn-glycero-3-phosphoglycerol	HMDB
GPG(18:1N9/16:0)	HMDB
GPG(18:1W9/16:0)	HMDB
PG(18:1N9/16:0)	HMDB
PG(18:1W9/16:0)	HMDB
Phosphatidylglycerol(18:1n9/16:0)	HMDB
Phosphatidylglycerol(18:1W9/16:0)	HMDB
1-(9Z-Octadecenoyl)-2-hexadecanoyl-sn-glycero-3-phosphoglycerol	HMDB
1-Oleoyl-2-palmitoyl-GPG	HMDB
1-Oleoyl-2-palmitoyl-sn-glycero-3-phospho-(1'-glycerol)	HMDB
1-Oleoyl-2-palmitoyl-sn-glycero-3-phospho-(1’-glycerol)	HMDB
GPG(18:1(9Z)/16:0)	HMDB
Phosphatidylglycerol(18:1(9Z)/16:0)	HMDB
PG(18:1(9Z)/16:0)	Lipid Annotator

Chemical Formula:

C₄₀H₇₇O₁₀P

Weight:

Average: 749.0071
Monoisotopic: 748.525435196

InChI Key:

GTCKEWVHTGGUSN-HGWHEPCSSA-N

InChI:

InChI=1S/C40H77O10P/c1-3-5-7-9-11-13-15-17-18-20-21-23-25-27-29-31-39(43)47-35-38(36-49-51(45,46)48-34-37(42)33-41)50-40(44)32-30-28-26-24-22-19-16-14-12-10-8-6-4-2/h17-18,37-38,41-42H,3-16,19-36H2,1-2H3,(H,45,46)/b18-17-/t37-,38+/m0/s1

CAS number:

Not Available

IUPAC Name:

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

Traditional IUPAC Name:

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

SMILES:

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

1,2-diacyl-sn-glycero-3-phospho-(1'-sn-glycerol) (CHEBI:73206 )
Diacylglycerophosphoglycerols (LMGP04010962 )

Physical Properties

State:

Not Available

Charge:

-1

Melting point:

Not Available

Experimental Properties:

Property	Value	Source

Predicted Properties

Property	Value	Source
Water Solubility	0.0001 g/L	ALOGPS
logP	8.17	ALOGPS
logP	11.46	ChemAxon
logS	-6.9	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	41	ChemAxon
Refractivity	205.63 m³·mol⁻¹	ChemAxon
Polarizability	91.38 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:

PGP(16:0/18:1(9Z)) + Water > PG(16:0/18:1(9Z)) + Phosphate
PE(17:0cycw7c/17:0cycw7c) + PG(16:0/18:1(9Z)) > Ethanolamine + CL(16:0/17:0cycw7c/17:0cycw7c/18:1(9Z))
PE(17:0cycw7c/17:0cycw7c) + PG(16:0/18:1(9Z)) > CL(16:0/17:0cycw7c/18:1(9Z)/17:0cycw7c) + Ethanolamine
PE(17:0cycw7c/17:0cycw7c) + PG(16:0/18:1(9Z)) > Ethanolamine + CL(16:0/18:1(9Z)/17:0cycw7c/17:0cycw7c)
PE(19:iso/19:0cycv8c) + PG(16:0/18:1(9Z)) > Ethanolamine + CL(16:0/18:1(9Z)/19:0cycv8c/19:0cycv8c)
PG(16:0/18:1(9Z)) + PE(19:iso/19:iso) > Ethanolamine + CL(16:0/19:0cycv8c/18:1(9Z)/19:0cycv8c)
PE(19:iso/19:iso) + PG(16:0/18:1(9Z)) > Ethanolamine + CL(16:0/19:0cycv8c/19:0cycv8c/18:1(9Z))
PE(17:0cycw7c/17:0cycw7c) + PG(16:0/18:1(9Z)) > Ethanolamine + CL(17:0cycw7c/16:0/17:0cycw7c/18:1(9Z))
PE(17:0cycw7c/17:0cycw7c) + PG(16:0/18:1(9Z)) > CL(17:0cycw7c/16:0/18:1(9Z)/17:0cycw7c) + Ethanolamine
PE(15:0/18:1(9Z)) + PG(16:0/18:1(9Z)) > Ethanolamine + CL(18:1(9Z)/15:0cyclo/16:0/18:1(9Z))
PE(19:0cycv8c/19:iso) + PG(16:0/18:1(9Z)) > Ethanolamine + CL(19:0cycv8c/16:0/18:1(9Z)/19:0cycv8c)

SMPDB Pathways:

phospholipid biosynthesis (CL(18:1(9Z)/15:0cyclo/16:0/18:1(9Z)))	PW001518
phospholipid biosynthesis (CL(19:0cycv8c/16:0/18:1(9Z)/19:0cycv8c))	PW001334
phospholipid biosynthesis CL(16:0/17:0cycw7c/17:0cycw7c/18:1(9Z))	PW001348
phospholipid biosynthesis CL(16:0/17:0cycw7c/18:1(9Z)/17:0cycw7c)	PW001350
phospholipid biosynthesis CL(16:0/18:1(9Z)/17:0cycw7c/17:0cycw7c)	PW001365
phospholipid biosynthesis CL(16:0/18:1(9Z)/19:0cycv8c/19:0cycv8c)	PW001381
phospholipid biosynthesis CL(16:0/19:0cycv8c/18:1(9Z)/19:0cycv8c)	PW001409
phospholipid biosynthesis CL(16:0/19:0cycv8c/19:0cycv8c/18:1(9Z))	PW001413
phospholipid biosynthesis CL(16:1(9Z)/17:0cycw7c/17:0cycw7c/18:1(9Z))	PW001565
phospholipid biosynthesis CL(17:0cycw7c/16:0/17:0cycw7c/18:1(9Z))	PW001684
phospholipid biosynthesis CL(17:0cycw7c/16:0/18:1(9Z)/17:0cycw7c)	PW001690

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	splash10-017v-3190520500-9e49914c88c80e67b390	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00p0-4291311100-32f3d951cc40e9104fc2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-05br-9083221000-0f34b30ee5894adf3ac9	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-06sj-0190200200-42a24e8e202dfd4937f4	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01si-4290100000-7d8c4a95374ecdeff64a	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9030000000-fa08da539f300400a5ca	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0000000900-2b6e33dc3e3568f4d2fd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a61-0090300400-f3f2ad392aa2f94f83cd	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-053s-0190300400-41a2c1de2632833af2ef	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	73206
HMDB ID	HMDB0010630
Pubchem Compound ID	52927225
Kegg ID	Not Available
ChemSpider ID	24768129
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 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(16:0/18:1(9Z)) (ECMDB24132) (M2MDB006249)

Structure for #<Compound:0x9c99b280>

Enzymes

Reactions

Reactions

Reactions