LPA(18:0/0:0) (ECMDB24101) (M2MDB006218)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes (2)XML
Proteins (2)
Record Information
Version2.0
Creation Date2015-09-08 17:49:19 -0600
Update Date2015-09-08 17:49:19 -0600
Secondary Accession Numbers
  • ECMDB24101
Identification
Name:LPA(18:0/0:0)
Description
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
ValueSource
Lysophosphatidic acid(18:0/0:0)HMDB
Lysophosphatidic acid(18:0)HMDB
LPA(18:0)HMDB
LPA(18:0/0:0)HMDB
1-Stearoyl-glycero-3-phosphateHMDB
1-Octadecanoyl-glycero-3-phosphateHMDB
1-Octadecanoyl-phosphatidic acidHMDB
Chemical Formula:C21H43O7P
Weight:Average: 438.5357
Monoisotopic: 438.274640242
InChI Key:LAYXSTYJRSVXIH-HXUWFJFHSA-N
InChI:InChI=1S/C21H43O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h20,22H,2-19H2,1H3,(H2,24,25,26)/t20-/m1/s1
CAS number:Not Available
IUPAC Name:[2-hydroxy-3-(octadecanoyloxy)propoxy]phosphonic acid
Traditional IUPAC Name:2-hydroxy-3-(octadecanoyloxy)propoxyphosphonic acid
SMILES:[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCC)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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent1-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 FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0015 g/LALOGPS
logP5.01ALOGPS
logP5.85ChemAxon
logS-5.5ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity114.18 m³·mol⁻¹ChemAxon
Polarizability51.46 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Membrane
Reactions:
acyl-[acp] + Glycerol 3-phosphate > a holo-[acyl-carrier protein] + LPA(18:0/0:0)
long-chain fatty acyl-CoA + Glycerol 3-phosphate > Coenzyme A + LPA(18:0/0:0)
acyl-[acp] + LPA(18:0/0:0) > PA(18:0/18:0) + a holo-[acyl-carrier protein]
long-chain fatty acyl-CoA + LPA(18:0/0:0) > PA(18:0/18:0) + Coenzyme A
SMPDB Pathways:
phospholipid biosynthesis I (18:0, 18:0)PW001001 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-01c0-5960100000-e8bdb4be1a18946029bcView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000900000-3f0129a711c87376aadfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000900000-3f0129a711c87376aadfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0950700000-720376636fb9cfa2ab8cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0000900000-5f9b7c55b2d415f2c32bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000i-0000900000-5f9b7c55b2d415f2c32bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0uei-2950600000-22fd9257845e128dd295View in MoNA
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDHMDB0007854
Pubchem Compound ID89567
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Glycerol-3-phosphate acyltransferase
General function:
Involved in transferase activity, transferring acyl groups
Specific function:
Catalyzes the transfer of an acyl group from acyl-ACP to glycerol-3-phosphate (G3P) to form lysophosphatidic acid (LPA). This enzyme can utilize either acyl-CoA or acyl-ACP as the fatty acyl donor
Gene Name:
plsB
Uniprot ID:
P0A7A7
Molecular weight:
91381
Reactions
Acyl-CoA + sn-glycerol 3-phosphate = CoA + 1-acyl-sn-glycerol 3-phosphate.
Protein Details
2. 1-acyl-sn-glycerol-3-phosphate acyltransferase
General function:
Involved in transferase activity, transferring acyl groups
Specific function:
Converts lysophosphatidic acid (LPA) into phosphatidic acid by incorporating an acyl moiety at the 2 position. This enzyme can utilize either acyl-CoA or acyl-ACP as the fatty acyl donor
Gene Name:
plsC
Uniprot ID:
P26647
Molecular weight:
27453
Reactions
Acyl-CoA + 1-acyl-sn-glycerol 3-phosphate = CoA + 1,2-diacyl-sn-glycerol 3-phosphate.
Acyl-[acyl-carrier-protein] + 1-acyl-sn-glycerol 3-phosphate = [acyl-carrier-protein] + 1,2-diacyl-sn-glycerol 3-phosphate.