PGP(23:1(9Z)/25:0) (YMDB14684)

Identification

YMDB ID

YMDB14684

Name

PGP(23:1(9Z)/25:0)

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

PGP(23:1(9Z)/25:0) 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(23:1(9Z)/25:0), in particular, consists of one 9Z-tricosanoyl chain to the C-1 atom, and one pentacosanoyl 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)-2-Hydroxy-3-({hydroxy[(2R)-2-(pentacosanoyloxy)-3-[(9Z)-tricos-9-enoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonate

CAS number

Not Available

Weight

Average: 1025.377
Monoisotopic: 1024.710867469

InChI Key

JNLWPWYFWKNADU-YHTUEJPNSA-N

InChI

InChI=1S/C54H106O13P2/c1-3-5-7-9-11-13-15-17-19-21-23-25-26-28-30-32-34-36-38-40-42-44-46-54(57)67-52(50-66-69(61,62)65-48-51(55)47-64-68(58,59)60)49-63-53(56)45-43-41-39-37-35-33-31-29-27-24-22-20-18-16-14-12-10-8-6-4-2/h29,31,51-52,55H,3-28,30,32-50H2,1-2H3,(H,61,62)(H2,58,59,60)/b31-29-/t51-,52+/m0/s1

IUPAC Name

[(2S)-2-hydroxy-3-({hydroxy[(2R)-2-(pentacosanoyloxy)-3-[(9Z)-tricos-9-enoyloxy]propoxy]phosphoryl}oxy)propoxy]phosphonic acid

Traditional IUPAC Name

(2S)-2-hydroxy-3-{[hydroxy((2R)-2-(pentacosanoyloxy)-3-[(9Z)-tricos-9-enoyloxy]propoxy)phosphoryl]oxy}propoxyphosphonic acid

Chemical Formula

C₅₄H₁₀₆O₁₃P₂

SMILES

[H][C@](O)(COP(O)(O)=O)COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCC\C=C/CCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCCCCCCCCCCC

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	0.00019 g/L	ALOGPS
logP	9.14	ALOGPS
logP	17.56	ChemAxon
logS	-6.7	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	57	ChemAxon
Refractivity	280.91 m³·mol⁻¹	ChemAxon
Polarizability	125.26 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	splash10-0ar0-7219005111-b3db05629a794672b93c	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ap0-4319002111-1f939ad9a91bb466aa0a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-8319210312-5af20053a2166bb88a11	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0f89-5019002000-761ee2a326abeaed6b37	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fb9-9014000000-46345e135621e70b68cf	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9001000000-7b4ebb6ffa830f5508f8	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:0xab32386c>