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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-09-09 02:38:47 UTC
Update Date2022-11-30 19:25:54 UTC
HMDB IDHMDB0114765
Secondary Accession NumbersNone
Metabolite Identification
Common NameLysoPA(i-14:0/0:0)
DescriptionLysoPA(i-14:0/0:0) 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. LysoPA(i-14:0/0:0), in particular, consists of one chain of isotetradecanoic acid at the C-1 position. 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.
Structure
Data?1563873518
Synonyms
ValueSource
1-Isotetradecanoyl-glycero-3-phosphateHMDB
1-Isotetradecanoyl-lysophosphatidic acidHMDB
LPA(i-14:0)HMDB
Lysophosphatidic acid(i-14:0/0:0)HMDB
Lysophosphatidic acid(i-14:0)HMDB
LPA(i-14:0/0:0)HMDB
LPA(14:0)HMDB
Lysophosphatidic acid(14:0)HMDB
1-Isotetradecanoyl-phosphatidic acidHMDB
Chemical FormulaC17H35O7P
Average Molecular Weight382.434
Monoisotopic Molecular Weight382.212040465
IUPAC Name{2-hydroxy-3-[(12-methyltridecanoyl)oxy]propoxy}phosphonic acid
Traditional Name2-hydroxy-3-[(12-methyltridecanoyl)oxy]propoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
CC(C)CCCCCCCCCCC(=O)OCC(O)COP(O)(O)=O
InChI Identifier
InChI=1S/C17H35O7P/c1-15(2)11-9-7-5-3-4-6-8-10-12-17(19)23-13-16(18)14-24-25(20,21)22/h15-16,18H,3-14H2,1-2H3,(H2,20,21,22)
InChI KeyQWRVNPWTRIUQKD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1-acylglycerol-3-phosphates. These are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct Parent1-acylglycerol-3-phosphates
Alternative Parents
Substituents
  • 1-acylglycerol-3-phosphate
  • Fatty acid ester
  • Monoalkyl phosphate
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Alcohol
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
DispositionNot Available
Process
Naturally occurring process
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
logP2.85ALOGPS
logP3.91ChemAxon
logS-4.4ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area113.29 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity95.73 m³·mol⁻¹ChemAxon
Polarizability42.69 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+192.69631661259
DarkChem[M-H]-187.64331661259
DeepCCS[M+H]+182.61830932474
DeepCCS[M-H]-179.70430932474
DeepCCS[M-2H]-213.73730932474
DeepCCS[M+Na]+190.36530932474
AllCCS[M+H]+197.432859911
AllCCS[M+H-H2O]+195.232859911
AllCCS[M+NH4]+199.632859911
AllCCS[M+Na]+200.232859911
AllCCS[M-H]-191.832859911
AllCCS[M+Na-2H]-193.632859911
AllCCS[M+HCOO]-195.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
LysoPA(i-14:0/0:0)CC(C)CCCCCCCCCCC(=O)OCC(O)COP(O)(O)=O3678.6Standard polar33892256
LysoPA(i-14:0/0:0)CC(C)CCCCCCCCCCC(=O)OCC(O)COP(O)(O)=O2421.3Standard non polar33892256
LysoPA(i-14:0/0:0)CC(C)CCCCCCCCCCC(=O)OCC(O)COP(O)(O)=O2837.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
LysoPA(i-14:0/0:0),1TMS,isomer #1CC(C)CCCCCCCCCCC(=O)OCC(COP(=O)(O)O)O[Si](C)(C)C2864.6Semi standard non polar33892256
LysoPA(i-14:0/0:0),1TMS,isomer #2CC(C)CCCCCCCCCCC(=O)OCC(O)COP(=O)(O)O[Si](C)(C)C2849.9Semi standard non polar33892256
LysoPA(i-14:0/0:0),2TMS,isomer #1CC(C)CCCCCCCCCCC(=O)OCC(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C2864.1Semi standard non polar33892256
LysoPA(i-14:0/0:0),2TMS,isomer #1CC(C)CCCCCCCCCCC(=O)OCC(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C2687.5Standard non polar33892256
LysoPA(i-14:0/0:0),2TMS,isomer #1CC(C)CCCCCCCCCCC(=O)OCC(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C3430.8Standard polar33892256
LysoPA(i-14:0/0:0),2TMS,isomer #2CC(C)CCCCCCCCCCC(=O)OCC(O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2874.0Semi standard non polar33892256
LysoPA(i-14:0/0:0),2TMS,isomer #2CC(C)CCCCCCCCCCC(=O)OCC(O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2682.7Standard non polar33892256
LysoPA(i-14:0/0:0),2TMS,isomer #2CC(C)CCCCCCCCCCC(=O)OCC(O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3156.1Standard polar33892256
LysoPA(i-14:0/0:0),3TMS,isomer #1CC(C)CCCCCCCCCCC(=O)OCC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2872.3Semi standard non polar33892256
LysoPA(i-14:0/0:0),3TMS,isomer #1CC(C)CCCCCCCCCCC(=O)OCC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2748.5Standard non polar33892256
LysoPA(i-14:0/0:0),3TMS,isomer #1CC(C)CCCCCCCCCCC(=O)OCC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2990.9Standard polar33892256
LysoPA(i-14:0/0:0),1TBDMS,isomer #1CC(C)CCCCCCCCCCC(=O)OCC(COP(=O)(O)O)O[Si](C)(C)C(C)(C)C3131.6Semi standard non polar33892256
LysoPA(i-14:0/0:0),1TBDMS,isomer #2CC(C)CCCCCCCCCCC(=O)OCC(O)COP(=O)(O)O[Si](C)(C)C(C)(C)C3080.5Semi standard non polar33892256
LysoPA(i-14:0/0:0),2TBDMS,isomer #1CC(C)CCCCCCCCCCC(=O)OCC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3338.1Semi standard non polar33892256
LysoPA(i-14:0/0:0),2TBDMS,isomer #1CC(C)CCCCCCCCCCC(=O)OCC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2991.5Standard non polar33892256
LysoPA(i-14:0/0:0),2TBDMS,isomer #1CC(C)CCCCCCCCCCC(=O)OCC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3545.5Standard polar33892256
LysoPA(i-14:0/0:0),2TBDMS,isomer #2CC(C)CCCCCCCCCCC(=O)OCC(O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3310.0Semi standard non polar33892256
LysoPA(i-14:0/0:0),2TBDMS,isomer #2CC(C)CCCCCCCCCCC(=O)OCC(O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C2968.0Standard non polar33892256
LysoPA(i-14:0/0:0),2TBDMS,isomer #2CC(C)CCCCCCCCCCC(=O)OCC(O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3337.8Standard polar33892256
LysoPA(i-14:0/0:0),3TBDMS,isomer #1CC(C)CCCCCCCCCCC(=O)OCC(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3560.2Semi standard non polar33892256
LysoPA(i-14:0/0:0),3TBDMS,isomer #1CC(C)CCCCCCCCCCC(=O)OCC(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3156.1Standard non polar33892256
LysoPA(i-14:0/0:0),3TBDMS,isomer #1CC(C)CCCCCCCCCCC(=O)OCC(COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3227.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - LysoPA(i-14:0/0:0) GC-MS (1 TMS) - 70eV, Positivesplash10-03fs-9421000000-4aaa61b6b4947040be682017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - LysoPA(i-14:0/0:0) 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 - LysoPA(i-14:0/0:0) 10V, Positive-QTOFsplash10-001i-0009000000-5d141a336820399612f52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(i-14:0/0:0) 20V, Positive-QTOFsplash10-001i-0009000000-5d141a336820399612f52021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(i-14:0/0:0) 40V, Positive-QTOFsplash10-02mi-0957000000-bb4d7a4c6e719d94ea812021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(i-14:0/0:0) 10V, Negative-QTOFsplash10-001i-0009000000-0cf40b8b7adbde49f5802021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(i-14:0/0:0) 20V, Negative-QTOFsplash10-001i-0009000000-0cf40b8b7adbde49f5802021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - LysoPA(i-14:0/0:0) 40V, Negative-QTOFsplash10-0ugi-2956000000-1e1f2694e15d344f7ffa2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
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 IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound17786784
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  7. 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 ]
  8. 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 ]
  9. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  10. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.