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Record Information
Version1.0
Creation Date2016-09-30 23:45:45 UTC
Update Date2020-05-21 16:28:07 UTC
BMDB IDBMDB0007853
Secondary Accession Numbers
  • BMDB07853
Metabolite Identification
Common NameLPA(16:0/0:0)
DescriptionLysoPA(16:0/0:0) 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.LysoPA(16:0/0:0), in particular, consists of one hexadecanoyl 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
Thumb
Synonyms
ValueSource
1-Hexadecanoyl-sn-glycero-3-phosphateChEBI
1-Hexadecanoyl-sn-glycero-3-phosphoric acidGenerator
1-Palmitoylglycerol 3-phosphoric acidHMDB
1-Palmitoyl-sn-glycerol 3-phosphateHMDB
PLPAHMDB
1-Palmitoyl-lysophosphatidic acidHMDB
1-Palmitoyl-lysophosphatidic acid, (R)-isomerHMDB
1-Palmitoyl-rac-glycerol 3-phosphateHMDB
1-Palmitoyl-lysophosphatidic acid, sodium salt, (R)-isomerHMDB
Lysophosphatidic acid(16:0)HMDB
1-Palmitoyl-glycero-3-phosphateHMDB
1-Hexadecanoyl-phosphatidic acidHMDB
LPA(16:0)HMDB
LPA(16:0/0:0)HMDB
1-Hexadecanoyl-glycero-3-phosphateHMDB
Lysophosphatidic acid(16:0/0:0)HMDB
Chemical FormulaC19H39O7P
Average Molecular Weight410.4825
Monoisotopic Molecular Weight410.243340114
IUPAC Name[3-(hexadecanoyloxy)-2-hydroxypropoxy]phosphonic acid
Traditional NamePLPA
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)OCC(O)COP(O)(O)=O
InChI Identifier
InChI=1S/C19H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(21)25-16-18(20)17-26-27(22,23)24/h18,20H,2-17H2,1H3,(H2,22,23,24)
InChI KeyYNDYKPRNFWPPFU-UHFFFAOYSA-N
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 Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.87ALOGPS
logP4.96ChemAxon
logS-5.2ALOGPS
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 Count20ChemAxon
Refractivity104.98 m³·mol⁻¹ChemAxon
Polarizability47.18 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-02n9-5940100000-a5ca92d33fddeb085287View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08fr-2986700000-f3b30f5c39843042fd11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4s-3942000000-0e96d3c410d5f67cbc44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4s-6930000000-8e619c799b8a218b3a05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-4190300000-bb83e3f01055cbe6102fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9050000000-de299cedb3cf89da4492View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-f3fc94f808e80bf00353View in MoNA
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot ApplicableNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0007853
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB030254
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC04036
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound89566
PDB IDNot Available
ChEBI ID64023
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in alkylglycerophosphoethanolamine phosphodies
Specific function:
Hydrolyzes lysophospholipids to produce the signaling molecule lysophosphatidic acid (LPA) in extracellular fluids. Major substrate is lysophosphatidylcholine (PubMed:12119361). Also can act on sphingosylphosphorylcholine producing sphingosine-1-phosphate, a modulator of cell motility. Can hydrolyze, in vitro, bis-pNPP, to some extent pNP-TMP, and barely ATP. Involved in several motility-related processes such as angiogenesis and neurite outgrowth. Acts as an angiogenic factor by stimulating migration of smooth muscle cells and microtubule formation. Stimulates migration of melanoma cells, probably via a pertussis toxin-sensitive G protein. May have a role in induction of parturition. Possible involvement in cell proliferation and adipose tissue development. Tumor cell motility-stimulating factor (By similarity). Required for LPA production in activated platelets, cleaves the sn-1 lysophospholipids to generate sn-1 lysophosphatidic acids containing predominantly 18:2 and 20:4 fatty acids (By similarity). Shows a preference for the sn-1 to the sn-2 isomer of 1-O-alkyl-sn-glycero-3-phosphocholine (lyso-PAF) (By similarity).
Gene Name:
ENPP2
Uniprot ID:
A1A4K5
Molecular weight:
101717.0
General function:
Lipid transport and metabolism
Specific function:
Not Available
Gene Name:
GNPAT
Uniprot ID:
A4IF87
Molecular weight:
77664.0
Reactions
Palmityl-CoA + Glycerol 3-phosphate → Coenzyme A + LPA(16:0/0:0)details
General function:
Lipid transport and metabolism
Specific function:
Esterifies acyl-group from acyl-ACP to the sn-1 position of glycerol-3-phosphate, an essential step in glycerolipid biosynthesis.
Gene Name:
GPAM
Uniprot ID:
Q5GJ77
Molecular weight:
93144.0
Reactions
Glycerol 3-phosphate + Palmityl-CoA → LPA(16:0/0:0) + Coenzyme Adetails
General function:
Involved in G-protein coupled receptor protein signalin
Specific function:
Receptor for lysophosphatidic acid (LPA). Plays a role in the reorganization of the actin cytoskeleton, cell migration, differentiation and proliferation, and thereby contributes to the responses to tissue damage and infectious agents. Activates downstream signaling cascades via the G(i)/G(o), G(12)/G(13), and G(q) families of heteromeric G proteins. Signaling inhibits adenylyl cyclase activity and decreases cellular cAMP levels. Signaling triggers an increase of cytoplasmic Ca(2+) levels. Activates RALA; this leads to the activation of phospholipase C (PLC) and the formation of inositol 1,4,5-trisphosphate. Signaling mediates activation of down-stream MAP kinases. Contributes to the regulation of cell shape. Promotes Rho-dependent reorganization of the actin cytoskeleton in neuronal cells and neurite retraction. Promotes the activation of Rho and the formation of actin stress fibers. Promotes formation of lamellipodia at the leading edge of migrating cells via activation of RAC1. Through its function as lysophosphatidic acid receptor, plays a role in chemotaxis and cell migration, including responses to injury and wounding. Plays a role in triggering inflammation in response to bacterial lipopolysaccharide (LPS) via its interaction with CD14. Promotes cell proliferation in response to lysophosphatidic acid. Required for normal skeleton development. May play a role in osteoblast differentiation. Required for normal brain development. Required for normal proliferation, survival and maturation of newly formed neurons in the adult dentate gyrus. Plays a role in pain perception and in the initiation of neuropathic pain.
Gene Name:
LPAR1
Uniprot ID:
Q28031
Molecular weight:
41070.0
General function:
Involved in purinergic nucleotide receptor activity, G-
Specific function:
Receptor for lysophosphatidic acid (LPA), a mediator of diverse cellular activities.
Gene Name:
LPAR5
Uniprot ID:
Q3ZC80
Molecular weight:
40639.0
General function:
Not Available
Specific function:
Converts 1-acyl-sn-glycerol-3-phosphate (lysophosphatidic acid or LPA) into 1,2-diacyl-sn-glycerol-3-phosphate (phosphatidic acid or PA) by incorporating an acyl moiety at the sn-2 position of the glycerol backbone.
Gene Name:
AGPAT1
Uniprot ID:
Q95JH2
Molecular weight:
32005.0
Reactions
LPA(16:0/0:0) + Palmityl-CoA → Coenzyme A + PA(16:0/16:0)details
LPA(16:0/0:0) + Stearoyl-CoA → Coenzyme A + PA(16:0/18:0)details
LPA(16:0/0:0) + Oleoyl-CoA → Coenzyme A + PA(16:0/18:1(9Z))details
LPA(16:0/0:0) + Gamma-linolenoyl-CoA → Coenzyme A + PA(16:0/18:3(6Z,9Z,12Z))details
LPA(16:0/0:0) + Eicosanoyl-CoA → Coenzyme A + PA(16:0/20:0)details
LPA(16:0/0:0) + Gondoyl-CoA → Coenzyme A + PA(16:0/20:1(11Z))details
LPA(16:0/0:0) + Docosanoyl-CoA → Coenzyme A + PA(16:0/22:0)details
LPA(16:0/0:0) + Erucoyl-CoA → Coenzyme A + PA(16:0/22:1(13Z))details
LPA(16:0/0:0) → PA(16:0/16:0)details
Palmityl-CoA + LPA(16:0/0:0) → PA(16:0/16:0) + Coenzyme Adetails
General function:
Not Available
Specific function:
Converts 1-acyl-sn-glycerol-3-phosphate (lysophosphatidic acid or LPA) into 1,2-diacyl-sn-glycerol-3-phosphate (phosphatidic acid or PA) by incorporating an acyl moiety at the sn-2 position of the glycerol backbone (By similarity). Exhibits high acyl-CoA specificity for polyunsaturated fatty acyl-CoA, especially docosahexaenoyl-CoA (22:6-CoA, DHA-CoA) (By similarity).
Gene Name:
AGPAT4
Uniprot ID:
Q5E9R2
Molecular weight:
43907.0
Reactions
LPA(16:0/0:0) + Palmityl-CoA → PA(16:0/16:0) + Coenzyme Adetails
LPA(16:0/0:0) + Stearoyl-CoA → PA(16:0/18:0) + Coenzyme Adetails
LPA(16:0/0:0) + Oleoyl-CoA → PA(16:0/18:1(9Z)) + Coenzyme Adetails