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Human Metabolome Database Version 3.5

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Showing metabocard for LPA(18:1(9Z)/0:0) (HMDB07855)

Record Information
Version 3.5
Creation Date 2008-09-11 19:27:14 -0600
Update Date 2013-02-08 17:17:53 -0700
HMDB ID HMDB07855
Secondary Accession Numbers
  • HMDB00443
Metabolite Identification
Common Name LPA(18:1(9Z)/0:0)
Description LPA(18:1(9Z)/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. 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 | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (2-hydroxy-3-phosphonooxypropyl) (E)-octadec-9-enoate
  2. (2-hydroxy-3-phosphonooxypropyl) (E)-octadec-9-enoic acid
  3. 1-(9Z-Octadecenoyl)-phosphatidic acid
  4. 1-Oleoyl-glycero-3-phosphate
  5. 1-Oleoyl-lyso-phosphatidate
  6. 1-Oleoyl-lyso-phosphatidic acid
  7. 1-Oleoyl-lysophosphatidate
  8. 1-Oleoyl-lysophosphatidic acid
  9. 1-Oleyllysophosphatidate
  10. 1-Oleyllysophosphatidic acid
  11. LPA(18:1(9Z)/0:0)
  12. LPA(18:1)
  13. LPA(18:1/0:0)
  14. LPA(18:1n9/0:0)
  15. LPA(18:1w9/0:0)
  16. LysoPA(18:1(9Z)/0:0)
  17. LysoPA(18:1)
  18. LysoPA(18:1w9/0:0)
  19. Lysophosphatidic acid(18:1)
  20. Lysophosphatidic acid(18:1/0:0)
  21. Lysophosphatidic acid(18:1n9/0:0)
  22. Lysophosphatidic acid(18:1w9/0:0)
  23. Monooleylphosphatidate
  24. Monooleylphosphatidic acid
  25. Oleoyl lysophosphatidate
  26. Oleoyl lysophosphatidic acid
Chemical Formula C21H41O7P
Average Molecular Weight 436.5198
Monoisotopic Molecular Weight 436.258990178
IUPAC Name [(2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propoxy]phosphonic acid
Traditional IUPAC Name (2R)-2-hydroxy-3-[(9Z)-octadec-9-enoyloxy]propoxyphosphonic acid
CAS Registry Number Not Available
SMILES CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@](O)([H])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)27-18-20(22)19-28-29(24,25)26/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26)/b10-9-/t20-/m1/s1
InChI Key WRGQSWVCFNIUNZ-GDCKJWNLSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Glycerophospholipids
Sub Class Glycerophosphates
Other Descriptors
  • Aliphatic Acyclic Compounds
Substituents
  • Acyclic Alkene
  • Carboxylic Acid Ester
  • Fatty Acid Ester
  • Organic Hypophosphite
  • Organic Phosphite
  • Phosphoric Acid Ester
  • Secondary Alcohol
Direct Parent Lysophosphatidic Acids
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 4.69 ALOGPS
LogP 5.49 ChemAxon
LogS -5.43 ALOGPS
pKa (strongest acidic) 1.51 ChemAxon
pKa (strongest basic) -3.4 ChemAxon
Hydrogen Acceptor Count 5 ChemAxon
Hydrogen Donor Count 3 ChemAxon
Polar Surface Area 113.29 A2 ChemAxon
Rotatable Bond Count 21 ChemAxon
Refractivity 115.3 ChemAxon
Polarizability 49.16 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
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB025048
KNApSAcK ID Not Available
Chemspider ID 4470776 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 HMDB07855 Link_out
Metagene Link HMDB07855 Link_out
METLIN ID Not Available
PubChem Compound 5311263 Link_out
PDB ID Not Available
ChEBI ID 62837 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available
Enzymes
Name: Phospholipase D2
Reactions:
  • a phosphatidylcholine + H2O = choline + a phosphatidate [RN:R01310]
Gene Name: PLD2
Uniprot ID: O14939 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Ectonucleotide pyrophosphatase/phosphodiesterase family member 2
Reactions:
  • 1-alkyl-sn-glycero-3-phosphoethanolamine + H2O = 1-alkyl-sn-glycerol 3-phosphate + ethanolamine [RN:R04362]
Gene Name: ENPP2
Uniprot ID: Q13822 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase theta
Reactions:
  • ATP + 1,2-diacyl-sn-glycerol = ADP + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02240]
Gene Name: DGKQ
Uniprot ID: P52824 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipid phosphate phosphohydrolase 2
Reactions:
  • a 1,2-diacylglycerol 3-phosphate + H2O = a 1,2-diacyl-sn-glycerol + phosphate [RN:R02239]
Gene Name: PPAP2C
Uniprot ID: O43688 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase alpha
Reactions:
  • ATP + 1,2-diacyl-sn-glycerol = ADP + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02240]
Gene Name: DGKA
Uniprot ID: P23743 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase delta
Reactions:
  • ATP + 1,2-diacyl-sn-glycerol = ADP + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02240]
Gene Name: DGKD
Uniprot ID: Q16760 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipid phosphate phosphohydrolase 1
Reactions:
  • a 1,2-diacylglycerol 3-phosphate + H2O = a 1,2-diacyl-sn-glycerol + phosphate [RN:R02239]
Gene Name: PPAP2A
Uniprot ID: O14494 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase beta
Reactions:
  • ATP + 1,2-diacyl-sn-glycerol = ADP + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02240]
Gene Name: DGKB
Uniprot ID: Q9Y6T7 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase iota
Reactions:
  • ATP + 1,2-diacyl-sn-glycerol = ADP + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02240]
Gene Name: DGKI
Uniprot ID: O75912 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lipid phosphate phosphohydrolase 3
Reactions:
  • a 1,2-diacylglycerol 3-phosphate + H2O = a 1,2-diacyl-sn-glycerol + phosphate [RN:R02239]
Gene Name: PPAP2B
Uniprot ID: O14495 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Diacylglycerol kinase zeta
Reactions:
  • ATP + 1,2-diacyl-sn-glycerol = ADP + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02240]
Gene Name: DGKZ
Uniprot ID: Q13574 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidate cytidylyltransferase 2
Reactions:
  • CTP + phosphatidate = diphosphate + CDP-diacylglycerol [RN:R01799]
Gene Name: CDS2
Uniprot ID: O95674 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Phosphatidate cytidylyltransferase 1
Reactions:
  • CTP + phosphatidate = diphosphate + CDP-diacylglycerol [RN:R01799]
Gene Name: CDS1
Uniprot ID: Q92903 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acyl-CoA:lysophosphatidylglycerol acyltransferase 1
Reactions:
    Gene Name: LPGAT1
    Uniprot ID: Q92604 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Focal adhesion kinase 1
    Reactions:
    • ATP + a [protein]-L-tyrosine = ADP + a [protein]-L-tyrosine phosphate [RN:R02584]
    Gene Name: PTK2
    Uniprot ID: Q05397 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Protein-tyrosine kinase 2-beta
    Reactions:
    • ATP + a [protein]-L-tyrosine = ADP + a [protein]-L-tyrosine phosphate [RN:R02584]
    Gene Name: PTK2B
    Uniprot ID: Q14289 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase gamma
    Reactions:
    • acyl-CoA + 1-acyl-sn-glycerol 3-phosphate = CoA + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02241]
    Gene Name: AGPAT3
    Uniprot ID: Q9NRZ7 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase beta
    Reactions:
    • acyl-CoA + 1-acyl-sn-glycerol 3-phosphate = CoA + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02241]
    Gene Name: AGPAT2
    Uniprot ID: O15120 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase alpha
    Reactions:
    • acyl-CoA + 1-acyl-sn-glycerol 3-phosphate = CoA + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02241]
    Gene Name: AGPAT1
    Uniprot ID: Q99943 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Phosphatidylinositol-glycan-specific phospholipase D
    Reactions:
    • 6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O = 6-(alpha-D-glucosaminyl)-1D-myo-inositol + 3-sn-phosphatidate [RN:R06623]
    Gene Name: GPLD1
    Uniprot ID: P80108 Link_out
    Protein Sequence: FASTA
    Gene Sequence: FASTA
    Name: Lysophosphatidic acid receptor 2
    Reactions:
      Gene Name: LPAR2
      Uniprot ID: Q9HBW0 Link_out
      Protein Sequence: FASTA
      Gene Sequence: FASTA
      Name: Lysophosphatidic acid receptor 1
      Reactions:
        Gene Name: LPAR1
        Uniprot ID: Q92633 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase epsilon
        Reactions:
        • acyl-CoA + 1-acyl-sn-glycerol 3-phosphate = CoA + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02241]
        Gene Name: AGPAT5
        Uniprot ID: Q9NUQ2 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Glycerol-3-phosphate acyltransferase 4
        Reactions:
        • acyl-CoA + sn-glycerol 3-phosphate = CoA + 1-acyl-sn-glycerol 3-phosphate [RN:R00851]
        Gene Name: AGPAT6
        Uniprot ID: Q86UL3 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Diacylglycerol kinase eta
        Reactions:
        • ATP + 1,2-diacyl-sn-glycerol = ADP + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02240]
        Gene Name: DGKH
        Uniprot ID: Q86XP1 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: 1-acyl-sn-glycerol-3-phosphate acyltransferase delta
        Reactions:
        • acyl-CoA + 1-acyl-sn-glycerol 3-phosphate = CoA + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02241]
        Gene Name: AGPAT4
        Uniprot ID: Q9NRZ5 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Lysophosphatidylcholine acyltransferase 1
        Reactions:
        • acetyl-CoA + 1-alkyl-sn-glycero-3-phosphocholine = CoA + 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine [RN:R03437]
        Gene Name: LPCAT1
        Uniprot ID: Q8NF37 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Lysophosphatidylcholine acyltransferase 2
        Reactions:
        • acetyl-CoA + 1-alkyl-sn-glycero-3-phosphocholine = CoA + 2-acetyl-1-alkyl-sn-glycero-3-phosphocholine [RN:R03437]
        Gene Name: LPCAT2
        Uniprot ID: Q7L5N7 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Lysocardiolipin acyltransferase 1
        Reactions:
        • acyl-CoA + 1-acyl-sn-glycerol 3-phosphate = CoA + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02241]
        Gene Name: LCLAT1
        Uniprot ID: Q6UWP7 Link_out
        Protein Sequence: FASTA
        Gene Sequence: FASTA
        Name: Lysophosphatidic acid receptor 3
        Reactions:
          Gene Name: LPAR3
          Uniprot ID: Q9UBY5 Link_out
          Protein Sequence: FASTA
          Gene Sequence: FASTA
          Name: Lysophosphatidic acid receptor 4
          Reactions:
            Gene Name: LPAR4
            Uniprot ID: Q99677 Link_out
            Protein Sequence: FASTA
            Gene Sequence: FASTA
            Name: Lysophosphatidic acid receptor 5
            Reactions:
              Gene Name: LPAR5
              Uniprot ID: Q9H1C0 Link_out
              Protein Sequence: FASTA
              Gene Sequence: FASTA
              Name: Lysophospholipid acyltransferase LPCAT4
              Reactions:
                Gene Name: LPCAT4
                Uniprot ID: Q643R3 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: Glycerol-3-phosphate acyltransferase 3
                Reactions:
                • acyl-CoA + sn-glycerol 3-phosphate = CoA + 1-acyl-sn-glycerol 3-phosphate [RN:R00851]
                Gene Name: AGPAT9
                Uniprot ID: Q53EU6 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: Lysophosphatidic acid phosphatase type 6
                Reactions:
                • a phosphate monoester + H2O = an alcohol + phosphate [RN:R00626]
                Gene Name: ACP6
                Uniprot ID: Q9NPH0 Link_out
                Protein Sequence: FASTA
                Gene Sequence: FASTA
                Name: Lysophosphatidic acid receptor 6
                Reactions:
                  Gene Name: LPAR6
                  Uniprot ID: P43657 Link_out
                  Protein Sequence: FASTA
                  Gene Sequence: FASTA
                  Name: Lipase member H
                  Reactions:
                    Gene Name: LIPH
                    Uniprot ID: Q8WWY8 Link_out
                    Protein Sequence: FASTA
                    Gene Sequence: FASTA
                    Name: Lipase member I
                    Reactions:
                      Gene Name: LIPI
                      Uniprot ID: Q6XZB0 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Lipid phosphate phosphatase-related protein type 4
                      Reactions:
                      • a 1,2-diacylglycerol 3-phosphate + H2O = a 1,2-diacyl-sn-glycerol + phosphate [RN:R02239]
                      Gene Name: LPPR4
                      Uniprot ID: Q7Z2D5 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Acylglycerol kinase, mitochondrial
                      Reactions:
                      • ATP + 1,2-diacyl-sn-glycerol = ADP + 1,2-diacyl-sn-glycerol 3-phosphate [RN:R02240]
                      Gene Name: AGK
                      Uniprot ID: Q53H12 Link_out
                      Protein Sequence: FASTA
                      Gene Sequence: FASTA
                      Name: Phospholipase D1 variant
                      Reactions:
                        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:
                          Gene Name: AGPAT6
                          Uniprot ID: Q2TU73 Link_out
                          Protein Sequence: FASTA
                          Gene Sequence: FASTA
                          Name: Diacylglycerol kinase, epsilon 64kDa
                          Reactions:
                            Gene Name: DGKE
                            Uniprot ID: A1L4Q0 Link_out
                            Protein Sequence: FASTA
                            Gene Sequence: FASTA
                            Name: Lysophosphatidic acid receptor 1
                            Reactions:
                              Gene Name: LPAR1
                              Uniprot ID: B1AP63 Link_out
                              Protein Sequence: FASTA
                              Gene Sequence: FASTA
                              Name: High-affinity lysophosphatidic acid receptor homolog
                              Reactions:
                                Gene Name: Not Available
                                Uniprot ID: O43898 Link_out
                                Protein Sequence: FASTA
                                Gene Sequence: FASTA
                                Name: LPAR1 protein
                                Reactions:
                                  Gene Name: LPAR1
                                  Uniprot ID: Q6GPG7 Link_out
                                  Protein Sequence: FASTA
                                  Gene Sequence: FASTA