PGP(16:1(11Z)/27:1(9Z)) (YMDB14427)

Identification

YMDB ID

YMDB14427

Name

PGP(16:1(11Z)/27:1(9Z))

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

PGP(16:1(11Z)/27:1(9Z)) belongs to the class of glycerophosphoglycerophosphates, also called phosphatidylglycerophosphates (PGPs). These lipids contain a common glycerophosphate skeleton linked to at least one fatty acyl chain and a glycero-3-phosphate moiety. As is the case with diacylglycerols, phosphatidylglycerophosphates can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 positions. PGP(16:1(11Z)/27:1(9Z)), in particular, consists of one 11Z-hexadecenoyl chain to the C-1 atom, and one 9Z-heptacosanoyl to the C-2 atom. In E. coli, PGPs can be found in the cytoplasmic membrane. The are synthesized by the addition of glycerol 3-phosphate to a CDP-diacylglycerol. In turn, PGPs are dephosphorylated to Phosphatidylglycerols (PGs) by the enzyme Phosphatidylglycerophosphatase.

Structure

MOL SDF PDB SMILES InChI

Synonyms

[(2S)-3-({[(2R)-2-[(9Z)-heptacos-9-enoyloxy]-3-[(11Z)-hexadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonate

CAS number

Not Available

Weight

Average: 953.226
Monoisotopic: 952.616967083

InChI Key

UJKFQKIGAHWFNO-ARQWNQBWSA-N

InChI

InChI=1S/C49H94O13P2/c1-3-5-7-9-11-13-15-17-18-19-20-21-22-23-24-25-26-27-29-31-33-35-37-39-41-49(52)62-47(45-61-64(56,57)60-43-46(50)42-59-63(53,54)55)44-58-48(51)40-38-36-34-32-30-28-16-14-12-10-8-6-4-2/h10,12,26-27,46-47,50H,3-9,11,13-25,28-45H2,1-2H3,(H,56,57)(H2,53,54,55)/b12-10-,27-26-/t46-,47+/m0/s1

IUPAC Name

[(2S)-3-({[(2R)-2-[(9Z)-heptacos-9-enoyloxy]-3-[(11Z)-hexadec-11-enoyloxy]propoxy](hydroxy)phosphoryl}oxy)-2-hydroxypropoxy]phosphonic acid

Traditional IUPAC Name

(2S)-3-{[(2R)-2-[(9Z)-heptacos-9-enoyloxy]-3-[(11Z)-hexadec-11-enoyloxy]propoxy(hydroxy)phosphoryl]oxy}-2-hydroxypropoxyphosphonic acid

Chemical Formula

C₄₉H₉₄O₁₃P₂

SMILES

[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCC\C=C/CCCC)OC(=O)CCCCCCC\C=C/CCCCCCCCCCCCCCCCC

Chemical Taxonomy

Physical Properties

State

Solid

Charge

Melting point

Not Available

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.00028 g/L	ALOGPS
logP	8.62	ALOGPS
logP	14.98	ChemAxon
logS	-6.5	ALOGPS
pKa (Strongest Acidic)	1.35	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-3	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	195.35 Å²	ChemAxon
Rotatable Bond Count	51	ChemAxon
Refractivity	259.03 m³·mol⁻¹	ChemAxon
Polarizability	113.58 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

Mitochondrion membrane

Organoleptic Properties

Not Available

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0k9j-1485233339-ed360a918f15c80642dc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-4689022513-d553f72d1de22f36c5a6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9547202240-03c1fa27ecc9abefe13c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0ug0-4091220102-97e729f9ad6510eda5c9	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fb9-9050000000-e31bffeca3057d551e1a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9000000000-9e2ce55d02008deb0309	JSpectraViewer

References

References:

Rattray JB, Schibeci A, Kidby DK. (1975). "Lipids of yeasts." Bacteriol Rev. 1975 Sep;39(3):197-231.240350

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	Not Available
HMDB ID	Not Available
Pubchem Compound ID	Not Available
Kegg ID	Not Available
ChemSpider ID	Not Available
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xb0943e04>