Lyso-PI(0:0/14:0) (YMDB13347)

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Identification

YMDB ID

YMDB13347

Name

Lyso-PI(0:0/14:0)

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Lyso-PI(0:0/14:0) is a lysophospholipid. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position.Lyso-PI(0:0/14:0), in particular, consists of one tetradecanoyl chain. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic however it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Some LPLs serve important signaling functions such as lysophosphatidic acid. Lysophosphatidylinositol is an endogenous lysophospholipid and endocannabinoid neurotransmitter.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

CAS number

Not Available

Weight

Average: 544.575
Monoisotopic: 544.264863887

InChI Key

KJKJVATVGMLDCK-UHFFFAOYSA-N

InChI

InChI=1S/C23H45O12P/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(25)34-16(14-24)15-33-36(31,32)35-23-21(29)19(27)18(26)20(28)22(23)30/h16,18-24,26-30H,2-15H2,1H3,(H,31,32)

IUPAC Name

[3-hydroxy-2-(tetradecanoyloxy)propoxy][(2,3,4,5,6-pentahydroxycyclohexyl)oxy]phosphinic acid

Traditional IUPAC Name

3-hydroxy-2-(tetradecanoyloxy)propoxy((2,3,4,5,6-pentahydroxycyclohexyl)oxy)phosphinic acid

Chemical Formula

C₂₃H₄₅O₁₂P

SMILES

CCCCCCCCCCCCCC(=O)OC(CO)COP(O)(=O)OC1C(O)C(O)C(O)C(O)C1O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 2-acyl-sn-glycerol-3-phosphoinositols. These are glycerophosphoinositols where the glycerol is acylated only at position O-2 with a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphoinositols

Direct Parent

2-acyl-sn-glycerol-3-phosphoinositols

Alternative Parents

Substituents

2-acyl-sn-glycerol-3-phosphoinositol
Inositol phosphate
Cyclohexanol
Fatty acid ester
Dialkyl phosphate
Cyclitol or derivatives
Fatty acyl
Organic phosphoric acid derivative
Phosphoric acid ester
Alkyl phosphate
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Polyol
Organooxygen compound
Alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Primary alcohol
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

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	1.11 g/L	ALOGPS
logP	1.59	ALOGPS
logP	1.18	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	1.83	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	203.44 Å²	ChemAxon
Rotatable Bond Count	20	ChemAxon
Refractivity	127.77 m³·mol⁻¹	ChemAxon
Polarizability	57.9 Å³	ChemAxon
Number of Rings	1	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

Cytoplasm

Organoleptic Properties

Not Available

SMPDB Pathways

Lysolipid incorporation into ER	PW002532
Lysolipid incorporation into ER PC(14:0/14:0)	PW002783
Lysolipid incorporation into Mitochondria	PW002531
Lysolipid incorporation into Mitochondria PC(14:0/14:0)	PW002792

KEGG Pathways

Not Available

SMPDB Reactions

Adenosine triphosphate + water + Lyso-PI(0:0/14:0) → ADP + phosphate + Lyso-PI(0:0/14:0)

Lyso-PI(0:0/14:0) → PI(14:0/14:0)

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03fs-1596060000-87d3929ca160d2387da2	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0400-3493010000-a591be4d92a91b2385be	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03fv-7920000000-0a250f808c2b5d950a24	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-002f-0096080000-d7a7dfe1d82244005e58	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-056r-7393020000-e86de1ed700eee1cc27f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9130000000-08ef190933a01f1df00a	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	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

Transporters

Protein Details

1. Probable phospholipid-transporting ATPase DNF2

General function:: Involved in nucleotide binding
Specific function:: This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of phospholipids. Required for protein transport from Golgi to vacuoles
Gene Name:: DNF2
Uniprot ID:: Q12675
Molecular weight:: 182617.0

Reactions

ATP + H(2)O + phospholipid(In) → ADP + phosphate + phospholipid(Out).

Protein Details

2. Probable phospholipid-transporting ATPase DNF1

General function:: Involved in nucleotide binding
Specific function:: This magnesium-dependent enzyme catalyzes the hydrolysis of ATP coupled with the transport of phospholipids (Potential)
Gene Name:: DNF1
Uniprot ID:: P32660
Molecular weight:: 177796.0

Reactions

ATP + H(2)O + phospholipid(In) → ADP + phosphate + phospholipid(Out).

Structure for #<Compound:0xb19d851c>

Transporters

Reactions

Reactions