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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:01:42 UTC
Update Date2022-03-07 02:51:26 UTC
HMDB IDHMDB0012496
Secondary Accession Numbers
  • HMDB12496
Metabolite Identification
Common Name1-Lyso-2-arachidonoyl-phosphatidate
DescriptionLPA(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 ). 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
Data?1582753061
Synonyms
ValueSource
1-Lyso-2-arachidonoyl-phosphatidic acidGenerator
2-(5Z,8Z,11Z,14Z)-Eicosatetraenoyl-sn-glycero-3-phosphateHMDB
2-(5Z,8Z,11Z,14Z)-Icosatetraenoyl-sn-glycero-3-phosphate(2-)HMDB
2-(5Z,8Z,11Z,14Z)-Eicosatetraenoyl-sn-glycero-3-phosphoric acidHMDB
2-(5Z,8Z,11Z,14Z)-Icosatetraenoyl-sn-glycero-3-phosphoric acid(2-)HMDB
1-Lyso-2-all-cis-5,8,11,14-eicosatetraenoyl-sn-glycero-3-phosphatidic acidHMDB
2-all-cis-5,8,11,14-Eicosatetraenoyl-lysophosphatidic acidHMDB
2-Arachidonoyl-lysophosphatidic acidHMDB
2-Arachidonoyl-sn-glycero-3-phosphateHMDB
L-beta-Arachidonoyl-alpha-lysophosphatidic acidHMDB
[3-Hydroxy-2-(icosa-5,8,11,14-tetraenoyloxy)propoxy]phosphonateHMDB
Chemical FormulaC23H39O7P
Average Molecular Weight458.532
Monoisotopic Molecular Weight458.243340594
IUPAC Name[3-hydroxy-2-(icosa-5,8,11,14-tetraenoyloxy)propoxy]phosphonic acid
Traditional Name3-hydroxy-2-(icosa-5,8,11,14-tetraenoyloxy)propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(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)
InChI KeyBDCFJMBXZCIVRH-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 2-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-2 position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent2-acylglycerol-3-phosphates
Alternative Parents
Substituents
  • 2-acylglycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Fatty acyl
  • Alkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Primary alcohol
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0034 g/LALOGPS
logP4.97ALOGPS
logP5.29ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity127.85 m³·mol⁻¹ChemAxon
Polarizability49.14 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+204.87830932474
DeepCCS[M-H]-202.32830932474
DeepCCS[M-2H]-236.25930932474
DeepCCS[M+Na]+212.54830932474
AllCCS[M+H]+216.232859911
AllCCS[M+H-H2O]+214.232859911
AllCCS[M+NH4]+218.032859911
AllCCS[M+Na]+218.532859911
AllCCS[M-H]-211.332859911
AllCCS[M+Na-2H]-214.532859911
AllCCS[M+HCOO]-218.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-Lyso-2-arachidonoyl-phosphatidateCCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(O)(O)=O3905.8Standard polar33892256
1-Lyso-2-arachidonoyl-phosphatidateCCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(O)(O)=O2888.3Standard non polar33892256
1-Lyso-2-arachidonoyl-phosphatidateCCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(O)(O)=O3395.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Lyso-2-arachidonoyl-phosphatidate,1TMS,isomer #1CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O)O3498.4Semi standard non polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,1TMS,isomer #2CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(=O)(O)O[Si](C)(C)C3441.3Semi standard non polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TMS,isomer #1CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O)O[Si](C)(C)C3473.7Semi standard non polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TMS,isomer #1CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O)O[Si](C)(C)C3162.0Standard non polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TMS,isomer #1CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O)O[Si](C)(C)C3865.7Standard polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TMS,isomer #2CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3429.1Semi standard non polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TMS,isomer #2CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3167.6Standard non polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TMS,isomer #2CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3663.7Standard polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,3TMS,isomer #1CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3457.2Semi standard non polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,3TMS,isomer #1CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3197.1Standard non polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,3TMS,isomer #1CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3320.8Standard polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,1TBDMS,isomer #1CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O)O3735.7Semi standard non polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,1TBDMS,isomer #2CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(=O)(O)O[Si](C)(C)C(C)(C)C3654.7Semi standard non polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TBDMS,isomer #1CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O)O[Si](C)(C)C(C)(C)C3923.9Semi standard non polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TBDMS,isomer #1CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O)O[Si](C)(C)C(C)(C)C3486.2Standard non polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TBDMS,isomer #1CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O)O[Si](C)(C)C(C)(C)C3902.6Standard polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TBDMS,isomer #2CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3858.0Semi standard non polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TBDMS,isomer #2CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3455.0Standard non polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,2TBDMS,isomer #2CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3753.2Standard polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,3TBDMS,isomer #1CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4083.9Semi standard non polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,3TBDMS,isomer #1CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3585.3Standard non polar33892256
1-Lyso-2-arachidonoyl-phosphatidate,3TBDMS,isomer #1CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC(CO[Si](C)(C)C(C)(C)C)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3474.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-Lyso-2-arachidonoyl-phosphatidate GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Lyso-2-arachidonoyl-phosphatidate 10V, Negative-QTOFsplash10-0a4i-4000900000-819e2d5b9aaa86be40d02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Lyso-2-arachidonoyl-phosphatidate 20V, Negative-QTOFsplash10-004j-9100000000-6307eb82a131f0391d312021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Lyso-2-arachidonoyl-phosphatidate 40V, Negative-QTOFsplash10-004i-9000000000-7e1087b9c9e914081e892021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Lyso-2-arachidonoyl-phosphatidate 10V, Positive-QTOFsplash10-08fr-0229500000-aa32372cdeaa104ea5192021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Lyso-2-arachidonoyl-phosphatidate 20V, Positive-QTOFsplash10-03dr-2398000000-0d4ebdc1c1453eec29972021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Lyso-2-arachidonoyl-phosphatidate 40V, Positive-QTOFsplash10-003v-9321000000-9e9c620862b97b08242c2021-09-22Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB029101
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound76043735
PDB IDNot Available
ChEBI ID78209
Food Biomarker OntologyNot Available
VMH IDCE3481
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gerrard JM, Clawson CC, White JG: Lysophosphatidic acids: III. Enhancement of neutrophil chemotaxis. Am J Pathol. 1980 Sep;100(3):609-18. [PubMed:7416233 ]
  2. Aoki J: Mechanisms of lysophosphatidic acid production. Semin Cell Dev Biol. 2004 Oct;15(5):477-89. [PubMed:15271293 ]
  3. Moritz A, De Graan PN, Gispen WH, Wirtz KW: Phosphatidic acid is a specific activator of phosphatidylinositol-4-phosphate kinase. J Biol Chem. 1992 Apr 15;267(11):7207-10. [PubMed:1313792 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  8. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  9. Moolenaar WH, Kruijer W, Tilly BC, Verlaan I, Bierman AJ, de Laat SW: Growth factor-like action of phosphatidic acid. Nature. 1986 Sep 11-17;323(6084):171-3. [PubMed:3748188 ]
  10. Yang CY, Frohman MA: Mitochondria: signaling with phosphatidic acid. Int J Biochem Cell Biol. 2012 Aug;44(8):1346-50. doi: 10.1016/j.biocel.2012.05.006. Epub 2012 May 15. [PubMed:22609101 ]
  11. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  12. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.