Human Metabolome Database Version 3.5

Showing metabocard for LPA(0:0/18:0) (HMDB07850)

Record Information
Version 3.5
Creation Date 2008-09-11 19:27:09 -0600
Update Date 2013-05-29 13:45:32 -0600
HMDB ID HMDB07850
Secondary Accession Numbers None
Metabolite Identification
Common Name LPA(0:0/18:0)
Description LPA(0:0/18:0) 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. 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 Link_out). 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 | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 2-Octadecanoyl-phosphatidic acid
  2. 2-Stearoyl-glycero-3-phosphate
  3. LPA(0:0/18:0)
  4. LPA(18:0)
  5. Lysophosphatidic acid(0:0/18:0)
  6. Lysophosphatidic acid(18:0)
Chemical Formula C21H43O7P
Average Molecular Weight 438.5357
Monoisotopic Molecular Weight 438.274640242
IUPAC Name [(2R)-3-hydroxy-2-(octadecanoyloxy)propoxy]phosphonic acid
Traditional IUPAC Name (2R)-3-hydroxy-2-(octadecanoyloxy)propoxyphosphonic acid
CAS Registry Number Not Available
SMILES [H][C@@](CO)(COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCCCC
InChI Identifier InChI=1S/C21H43O7P/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/h20,22H,2-19H2,1H3,(H2,24,25,26)/t20-/m1/s1
InChI Key RPAOEHFOGLEBTJ-HXUWFJFHSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class N/A
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Carboxylic Acid Ester
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
  • Primary Alcohol
Direct Parent Fatty Acid Esters
Ontology
Status Expected 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
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 0.0016 g/L ALOGPS
LogP 4.91 ALOGPS
LogP 5.85 ChemAxon
LogS -5.45 ALOGPS
pKa (strongest acidic) 1.32 ChemAxon
pKa (strongest basic) -3 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 113.29 A2 ChemAxon
Rotatable Bond Count 22 ChemAxon
Refractivity 114.18 ChemAxon
Polarizability 51.08 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location
  • All Tissues
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
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB025043
KNApSAcK ID Not Available
Chemspider ID 24766511 Link_out
KEGG Compound ID C00416 Link_out
BioCyc ID L-PHOSPHATIDATE Link_out
BiGG ID Not Available
Wikipedia Link Lecithin Link_out
NuGOwiki Link HMDB07850 Link_out
Metagene Link HMDB07850 Link_out
METLIN ID Not Available
PubChem Compound 53478600 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not 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 Link_out
  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 Link_out
  3. Aoki J: Mechanisms of lysophosphatidic acid production. Semin Cell Dev Biol. 2004 Oct;15(5):477-89. Pubmed: 15271293 Link_out

Enzymes
Name: Phospholipase D2
Reactions: Not Available
Gene Name: PLD2
Uniprot ID: O14939 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 2
Reactions: Not Available
Gene Name: ENPP2
Uniprot ID: Q13822 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase theta
Reactions: Not Available
Gene Name: DGKQ
Uniprot ID: P52824 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipid phosphate phosphohydrolase 2
Reactions: Not Available
Gene Name: PPAP2C
Uniprot ID: O43688 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase alpha
Reactions: Not Available
Gene Name: DGKA
Uniprot ID: P23743 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase delta
Reactions: Not Available
Gene Name: DGKD
Uniprot ID: Q16760 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipid phosphate phosphohydrolase 1
Reactions: Not Available
Gene Name: PPAP2A
Uniprot ID: O14494 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase beta
Reactions: Not Available
Gene Name: DGKB
Uniprot ID: Q9Y6T7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase iota
Reactions: Not Available
Gene Name: DGKI
Uniprot ID: O75912 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipid phosphate phosphohydrolase 3
Reactions: Not Available
Gene Name: PPAP2B
Uniprot ID: O14495 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase zeta
Reactions: Not Available
Gene Name: DGKZ
Uniprot ID: Q13574 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidate cytidylyltransferase 2
Reactions: Not Available
Gene Name: CDS2
Uniprot ID: O95674 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidate cytidylyltransferase 1
Reactions: Not Available
Gene Name: CDS1
Uniprot ID: Q92903 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acyl-CoA:lysophosphatidylglycerol acyltransferase 1
Reactions: Not Available
Gene Name: LPGAT1
Uniprot ID: Q92604 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Focal adhesion kinase 1
Reactions: Not Available
Gene Name: PTK2
Uniprot ID: Q05397 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Protein-tyrosine kinase 2-beta
Reactions: Not Available
Gene Name: PTK2B
Uniprot ID: Q14289 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase gamma
Reactions: Not Available
Gene Name: AGPAT3
Uniprot ID: Q9NRZ7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase beta
Reactions: Not Available
Gene Name: AGPAT2
Uniprot ID: O15120 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase alpha
Reactions: Not Available
Gene Name: AGPAT1
Uniprot ID: Q99943 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidylinositol-glycan-specific phospholipase D
Reactions: Not Available
Gene Name: GPLD1
Uniprot ID: P80108 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidic acid receptor 2
Reactions: Not Available
Gene Name: LPAR2
Uniprot ID: Q9HBW0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidic acid receptor 1
Reactions: Not Available
Gene Name: LPAR1
Uniprot ID: Q92633 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase epsilon
Reactions: Not Available
Gene Name: AGPAT5
Uniprot ID: Q9NUQ2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycerol-3-phosphate acyltransferase 4
Reactions: Not Available
Gene Name: AGPAT6
Uniprot ID: Q86UL3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase eta
Reactions: Not Available
Gene Name: DGKH
Uniprot ID: Q86XP1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase delta
Reactions: Not Available
Gene Name: AGPAT4
Uniprot ID: Q9NRZ5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidylcholine acyltransferase 1
Reactions: Not Available
Gene Name: LPCAT1
Uniprot ID: Q8NF37 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidylcholine acyltransferase 2
Reactions: Not Available
Gene Name: LPCAT2
Uniprot ID: Q7L5N7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysocardiolipin acyltransferase 1
Reactions: Not Available
Gene Name: LCLAT1
Uniprot ID: Q6UWP7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidic acid receptor 3
Reactions: Not Available
Gene Name: LPAR3
Uniprot ID: Q9UBY5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidic acid receptor 4
Reactions: Not Available
Gene Name: LPAR4
Uniprot ID: Q99677 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidic acid receptor 5
Reactions: Not Available
Gene Name: LPAR5
Uniprot ID: Q9H1C0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophospholipid acyltransferase LPCAT4
Reactions: Not Available
Gene Name: LPCAT4
Uniprot ID: Q643R3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glycerol-3-phosphate acyltransferase 3
Reactions: Not Available
Gene Name: AGPAT9
Uniprot ID: Q53EU6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidic acid phosphatase type 6
Reactions: Not Available
Gene Name: ACP6
Uniprot ID: Q9NPH0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidic acid receptor 6
Reactions: Not Available
Gene Name: LPAR6
Uniprot ID: P43657 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipase member H
Reactions: Not Available
Gene Name: LIPH
Uniprot ID: Q8WWY8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipase member I
Reactions: Not Available
Gene Name: LIPI
Uniprot ID: Q6XZB0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipid phosphate phosphatase-related protein type 4
Reactions: Not Available
Gene Name: LPPR4
Uniprot ID: Q7Z2D5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acylglycerol kinase, mitochondrial
Reactions: Not Available
Gene Name: AGK
Uniprot ID: Q53H12 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phospholipase D1 variant
Reactions: Not Available
Gene Name: Not Available
Uniprot ID: Q59EA4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 1-acylglycerol-3-phosphate O-acyltransferase 6 (Lysophosphatidic acid acyltransferase, zeta), isoform CRA_b
Reactions: Not Available
Gene Name: AGPAT6
Uniprot ID: Q2TU73 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase, epsilon 64kDa
Reactions: Not Available
Gene Name: DGKE
Uniprot ID: A1L4Q0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lysophosphatidic acid receptor 1
Reactions: Not Available
Gene Name: LPAR1
Uniprot ID: B1AP63 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: High-affinity lysophosphatidic acid receptor homolog
Reactions: Not Available
Gene Name: Not Available
Uniprot ID: O43898 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: LPAR1 protein
Reactions: Not Available
Gene Name: LPAR1
Uniprot ID: Q6GPG7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA