Showing metabocard for LPA(18:2(9Z,12Z)/0:0) (BMDB0007856)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 23:45:49 UTC
Update Date2020-05-11 19:24:57 UTC
BMDB IDBMDB0007856
Secondary Accession Numbers
  • BMDB07856
Metabolite Identification
Common NameLPA(18:2(9Z,12Z)/0:0)
Description1-linoleoyl-sn-glycerol 3-phosphate, also known as 1-linoleyl lysophosphatidic acid or PA(18:2(9Z,12Z)/0:0), 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. 1-linoleoyl-sn-glycerol 3-phosphate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(9Z,12Z-Octadecadienoyl)-glycero-3-phosphateChEBI
1-Linoleyl lysophosphatidic acidChEBI
1-Linoleyl-2-lyso-sn-glycerol 3-phosphatidic acidChEBI
1-Linoleylglycerol 3-phosphateChEBI
1-O-Linoleyl-sn-glycerol 3-phosphateChEBI
PA(18:2(9Z,12Z)/0:0)ChEBI
1-(9Z,12Z-Octadecadienoyl)-glycero-3-phosphoric acidGenerator
1-Linoleyl lysophosphatidateGenerator
1-Linoleyl-2-lyso-sn-glycerol 3-phosphatidateGenerator
1-Linoleylglycerol 3-phosphoric acidGenerator
1-O-Linoleyl-sn-glycerol 3-phosphoric acidGenerator
1-Linoleoyl-sn-glycerol 3-phosphoric acidGenerator
Chemical FormulaC21H39O7P
Average Molecular Weight434.5039
Monoisotopic Molecular Weight434.243340114
IUPAC Name[(2R)-2-hydroxy-3-[(9Z,12Z)-octadeca-9,12-dienoyloxy]propoxy]phosphonic acid
Traditional Name1-linoleylglycerol 3-phosphate
CAS Registry NumberNot Available
SMILES
CCCCC\C=C/C\C=C/CCCCCCCC(=O)OC[C@](O)([H])COP(O)(=O)O
InChI Identifier
InChI=1S/C21H39O7P/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/h6-7,9-10,20,22H,2-5,8,11-19H2,1H3,(H2,24,25,26)/b7-6-,10-9-/t20-/m1/s1
InChI KeyZQTAMPRZFOOEEP-KKFOGOCZSA-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
logP4.58ALOGPS
logP5.12ChemAxon
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
Refractivity116.42 m³·mol⁻¹ChemAxon
Polarizability47.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cell membrane
  • Intracellular membrane
  • Membrane
Biospecimen Locations
  • All Tissues
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
All TissuesExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound50990923
PDB IDNot Available
ChEBI ID62834
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Ectonucleotide pyrophosphatase/phosphodiesterase family member 2
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
Enzyme Details
2. Lysophosphatidic acid receptor 1
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
Enzyme Details
3. Lysophosphatidic acid receptor 5
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