Hmp_logo

Human Metabolome Database Version 3.5

HMDB has recently undergone some major changes, if you are experiencing problems please click here to provide us with feedback.

Showing metabocard for 1-Lyso-2-arachidonoyl-phosphatidate (HMDB12496)

Record Information
Version 3.5
Creation Date 2009-07-24 18:01:42 -0600
Update Date 2013-02-08 17:29:15 -0700
HMDB ID HMDB12496
Secondary Accession Numbers None
Metabolite Identification
Common Name 1-Lyso-2-arachidonoyl-phosphatidate
Description LPA(0:0/20:4n6) 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.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 Link_out). 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 Link_out).
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 1-Lyso-2-all-cis-5,8,11,14-eicosatetraenoyl-sn-glycero-3-phosphatidic acid
  2. 2-All-cis-5,8,11,14-eicosatetraenoyl-lysophosphatidic acid
  3. 2-Arachidonoyl-lysophosphatidic acid
  4. 2-Arachidonoyl-sn-glycero-3-phosphate
  5. L-beta-Arachidonoyl-alpha-lysophosphatidic acid
Chemical Formula C23H37O7P
Average Molecular Weight 456.5094
Monoisotopic Molecular Weight 456.22769005
IUPAC Name (2R)-1-hydroxy-3-(phosphonatooxy)propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
Traditional IUPAC Name (2R)-1-hydroxy-3-(phosphonatooxy)propan-2-yl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
CAS Registry Number Not Available
SMILES CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)O[C@H](CO)COP([O-])([O-])=O
InChI Identifier InChI=1S/C23H39O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)30-22(20-24)21-29-31(26,27)28/h6-7,9-10,12-13,15-16,22,24H,2-5,8,11,14,17-21H2,1H3,(H2,26,27,28)/p-2/b7-6-,10-9-,13-12-,16-15-/t22-/m1/s1
InChI Key BDCFJMBXZCIVRH-NZRYSPDRSA-L
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Eicosanoids
Sub Class Other Hydroxyeicosapolyenoic Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Acyclic Alkene
  • Carboxylic Acid Ester
  • Fatty Acid Ester
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
  • Primary Alcohol
Direct Parent Other Hydroxyeicosapolyenoic Acids
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 0.0034 g/L ALOGPS
LogP 5.57 ALOGPS
LogP 5.29 ChemAxon
LogS -5.16 ALOGPS
pKa (strongest acidic) 1.32 ChemAxon
pKa (strongest basic) -3 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 118.95 A2 ChemAxon
Rotatable Bond Count 20 ChemAxon
Refractivity 125.61 ChemAxon
Polarizability 49.07 ChemAxon
Formal Charge -2 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029101
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12496 Link_out
Metagene Link HMDB12496 Link_out
METLIN ID Not Available
PubChem Compound 53481443 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available