LPA(12:0/0:0) (YMDB13272)

Identification

YMDB ID

YMDB13272

Name

LPA(12:0/0:0)

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

LPA(12:0/0:0) is a lysophosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. Lysophosphatidic acids can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. Fatty acids containing 16 and 18 carbons are the most common.LPA(12:0/0:0), in particular, consists of one dodecanoyl chain. Lysophosphatidic acid is the simplest possible glycerophospholipid. It is the biosynthetic precursor of phosphatidic acid. Although it is present at very low levels only in animal tissues, it is extremely important biologically, influencing many biochemical processes.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Disodium lauroyl lysophosphatidate dihydrate
Lauroyl-lysophosphatidate
3-Lauroyl-glycero-1-phosphate, (R)-isomer
3-Lauroyl-glycero-1-phosphate

CAS number

Not Available

Weight

Average: 354.38
Monoisotopic: 354.180740336

InChI Key

STTKJLVEXMKLNA-UHFFFAOYSA-N

InChI

InChI=1S/C15H31O7P/c1-2-3-4-5-6-7-8-9-10-11-15(17)21-12-14(16)13-22-23(18,19)20/h14,16H,2-13H2,1H3,(H2,18,19,20)

IUPAC Name

[3-(dodecanoyloxy)-2-hydroxypropoxy]phosphonic acid

Traditional IUPAC Name

3-(dodecanoyloxy)-2-hydroxypropoxyphosphonic acid

Chemical Formula

C₁₅H₃₁O₇P

SMILES

CCCCCCCCCCCC(=O)OCC(O)COP(O)(O)=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerophospholipids

Sub Class

Glycerophosphates

Direct Parent

1-acylglycerol-3-phosphates

Alternative Parents

Substituents

1-acylglycerol-3-phosphate
Fatty acid ester
Monoalkyl phosphate
Fatty acyl
Alkyl phosphate
Phosphoric acid ester
Organic phosphoric acid derivative
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
Organooxygen compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	0.16 g/L	ALOGPS
logP	2.47	ALOGPS
logP	3.18	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	1.51	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	86.58 m³·mol⁻¹	ChemAxon
Polarizability	38.67 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	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
Endoplasmic reticulum

Organoleptic Properties

Not Available

SMPDB Pathways

Triacylglycerol metabolism TG(12:0/12:0/12:0)	PW007581
Triacylglycerol metabolism TG(12:0/12:0/14:0)	PW007587
Triacylglycerol metabolism TG(12:0/12:0/14:1(9Z))	PW007591
Triacylglycerol metabolism TG(12:0/12:0/16:0)	PW007596
Triacylglycerol metabolism TG(12:0/12:0/16:1(9Z))	PW007603

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 GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	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	134394
Kegg ID	Not Available
ChemSpider ID	Not Available
FOODB ID	Not Available
Wikipedia ID	Not Available
BioCyc ID	Not Available

Structure for #<Compound:0xabdae020>