Record Information
Version3.6
Creation Date2008-09-12 01:27:10 UTC
Update Date2013-05-29 19:45:33 UTC
HMDB IDHMDB07851
Secondary Accession NumbersNone
Metabolite Identification
Common NameLPA(0:0/18:1(9Z))
DescriptionLPA(0:0/18:1(9Z)) 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. 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. In particular, lysophosphatidic acid is an intercellular lipid mediator with growth factor-like activities, and is rapidly produced and released from activated platelets to influence target cells. 1-Palmitoyl lysophosphatidic acid is the major component of lysophosphatidic acid (LPA) in plasma, and is in a reduced ratio in individuals with gynecological cancers (PMID 11585410 ). LPA is a pluripotent lipid mediator controlling growth, motility, and differentiation, that has a strong influence on the chemotaxis and ultrastructure of human neutrophils (PMID 7416233 ). In serum and plasma, LPA is mainly converted from lysophospholipids, whereas in platelets and some cancer cells it is converted from phosphatidic acid. In each pathway, at least two phospholipase activities are required: phospholipase A1 (PLA1)/PLA2 plus lysophospholipase D (lysoPLD) activities are involved in the first pathway and phospholipase D (PLD) plus PLA1/PLA2 activities are involved in the second pathway. (PMID 15271293 ).
Structure
Thumb
Synonyms
  1. 2-(9Z-Octadecenoyl)-phosphatidic acid
  2. 2-Oleoyl-glycero-3-phosphate
  3. LPA(0:0/18:1)
  4. LPA(0:0/18:1n9)
  5. LPA(0:0/18:1w9)
  6. LPA(18:1)
  7. Lysophosphatidic acid(0:0/18:1)
  8. Lysophosphatidic acid(0:0/18:1n9)
  9. Lysophosphatidic acid(0:0/18:1w9)
  10. Lysophosphatidic acid(18:1)
Chemical FormulaC21H41O7P
Average Molecular Weight436.5198
Monoisotopic Molecular Weight436.258990178
IUPAC Name[(2R)-3-hydroxy-2-[(9Z)-octadec-9-enoyloxy]propoxy]phosphonic acid
Traditional IUPAC Name(2R)-3-hydroxy-2-[(9Z)-octadec-9-enoyloxy]propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCC\C=C/CCCCCCCC(=O)O[C@]([H])(CO)COP(O)(=O)O
InChI Identifier
InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)28-20(18-22)19-27-29(24,25)26/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26)/b10-9-/t20-/m1/s1
InChI KeyZOOLJLSXNRZLDH-GDCKJWNLSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acid Esters
Sub ClassN/A
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Acyclic Alkene
  • Carboxylic Acid Ester
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
  • Primary Alcohol
Direct ParentFatty Acid Esters
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Energy source
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane component
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • 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
water solubility0.0017 g/LALOGPS
logP4.7ALOGPS
logP5.49ChemAxon
logS-5.4ALOGPS
pKa (strongest acidic)1.32ChemAxon
pKa (strongest basic)-3ChemAxon
physiological charge-2ChemAxon
hydrogen acceptor count5ChemAxon
hydrogen donor count3ChemAxon
polar surface area113.29ChemAxon
rotatable bond count21ChemAxon
refractivity115.3ChemAxon
polarizability49.48ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue Location
  • All Tissues
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB025044
KNApSAcK IDNot Available
Chemspider ID24766512
KEGG Compound IDC00416
BioCyc IDL-PHOSPHATIDATE
BiGG IDNot Available
Wikipedia LinkLecithin
NuGOwiki LinkHMDB07851
Metagene LinkHMDB07851
METLIN IDNot Available
PubChem Compound52929749
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Shen Z, Wu M, Elson P, Kennedy AW, Belinson J, Casey G, Xu Y: Fatty acid composition of lysophosphatidic acid and lysophosphatidylinositol in plasma from patients with ovarian cancer and other gynecological diseases. Gynecol Oncol. 2001 Oct;83(1):25-30. Pubmed: 11585410
  2. Gerrard JM, Clawson CC, White JG: Lysophosphatidic acids: III. Enhancement of neutrophil chemotaxis. Am J Pathol. 1980 Sep;100(3):609-18. Pubmed: 7416233
  3. Aoki J: Mechanisms of lysophosphatidic acid production. Semin Cell Dev Biol. 2004 Oct;15(5):477-89. Pubmed: 15271293

Enzymes

Gene Name:
PLD2
Uniprot ID:
O14939
Gene Name:
DGKQ
Uniprot ID:
P52824
Gene Name:
PPAP2C
Uniprot ID:
O43688
Gene Name:
DGKA
Uniprot ID:
P23743
Gene Name:
DGKD
Uniprot ID:
Q16760
Gene Name:
PPAP2A
Uniprot ID:
O14494
Gene Name:
DGKB
Uniprot ID:
Q9Y6T7
Gene Name:
DGKI
Uniprot ID:
O75912
Gene Name:
PPAP2B
Uniprot ID:
O14495
Gene Name:
DGKZ
Uniprot ID:
Q13574
Gene Name:
CDS2
Uniprot ID:
O95674
Gene Name:
CDS1
Uniprot ID:
Q92903
Gene Name:
PTK2
Uniprot ID:
Q05397
Gene Name:
PTK2B
Uniprot ID:
Q14289
Gene Name:
LPAR2
Uniprot ID:
Q9HBW0
Gene Name:
LPAR1
Uniprot ID:
Q92633
Gene Name:
AGPAT6
Uniprot ID:
Q86UL3
Gene Name:
DGKH
Uniprot ID:
Q86XP1
Gene Name:
LCLAT1
Uniprot ID:
Q6UWP7
Gene Name:
LPAR3
Uniprot ID:
Q9UBY5
Gene Name:
LPAR4
Uniprot ID:
Q99677
Gene Name:
LPAR5
Uniprot ID:
Q9H1C0
Gene Name:
LPCAT4
Uniprot ID:
Q643R3
Gene Name:
AGPAT9
Uniprot ID:
Q53EU6
Gene Name:
LPAR6
Uniprot ID:
P43657
Gene Name:
LIPH
Uniprot ID:
Q8WWY8
Gene Name:
LIPI
Uniprot ID:
Q6XZB0
Gene Name:
AGK
Uniprot ID:
Q53H12
Gene Name:
Not Available
Uniprot ID:
Q59EA4
Gene Name:
DGKE
Uniprot ID:
A1L4Q0
Gene Name:
LPAR1
Uniprot ID:
B1AP63
Gene Name:
LPAR1
Uniprot ID:
Q6GPG7