P. aeruginosa Metabolome Database: PG(16:0/18:1(9Z)) (PAMDB006249)

Identification Taxonomy Physical Properties Biological Properties Spectra Concentrations Links References Enzymes Transporters

Proteins (3280)

Record Information

Version

1.0

Update Date

1/22/2018 11:54:54 AM

Metabolite ID

PAMDB006249

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 Pseudomonas aeruginosa 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 View Structure

Synonyms:

Not Available

Chemical Formula:

C₄₀H₇₇O₁₀P

Average Molecular Weight:

749.0071

Monoisotopic Molecular Weight:

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]propoxyphosphinic acid

SMILES:

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

Chemical Taxonomy

Taxonomy Description

This compound 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
Dialkyl phosphate
Fatty acid ester
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Organic phosphate
Dicarboxylic acid or derivatives
Saccharide
Secondary alcohol
Carboxylic acid ester
1,2-diol
Carboxylic acid derivative
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	0.000102 mg/mL	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	89.68 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)

Pathways:

Not Available

Spectra

Spectra:

Spectrum Type	Description	Splash Key
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

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	HMDB10630
Pubchem Compound ID	52927225
Kegg ID	Not Available
ChemSpider ID	24768129
Wikipedia ID	Not Available
BioCyc ID	Not Available

PG(16:0/18:1(9Z)) (PAMDB006249)

Structure for PG(16:0/18:1(9Z)) (PAMDB006249)