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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-16 03:43:30 UTC
Update Date2021-09-14 14:59:44 UTC
HMDB IDHMDB0062321
Secondary Accession Numbers
  • HMDB62321
Metabolite Identification
Common Name1-tetradecanoyl-sn-glycero-3-phosphate
Description1-tetradecanoyl-sn-glycero-3-phosphate, also known as 1-myristoyl lysophosphatidic acid or 1-myristoylglycerol 3-phosphate, 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. 1-tetradecanoyl-sn-glycero-3-phosphate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866295
Synonyms
ValueSource
(2R)-2-Hydroxy-3-(phosphonooxy)propyl myristateChEBI
1-Myristoyl lpaChEBI
1-Myristoyl lysophosphatidic acidChEBI
1-Myristoyl-2-lyso-sn-glycerol 3-phosphatidic acidChEBI
1-Myristoylglycerol 3-phosphateChEBI
1-O-Myristoyl-sn-glycerol 3-phosphateChEBI
1-O-Tetradecanoyl-sn-glycerol 3-phosphateChEBI
1-Tetradecanoyl-sn-glycerol 3-phosphateChEBI
1-Tetradecanoylglycerol 3-phosphateChEBI
Myristoyl lysophosphatidic acidChEBI
PA(14:0/0:0)ChEBI
(2R)-2-Hydroxy-3-(phosphonooxy)propyl myristic acidGenerator
1-Myristoyl lysophosphatidateGenerator
1-Myristoyl-2-lyso-sn-glycerol 3-phosphatidateGenerator
1-Myristoylglycerol 3-phosphoric acidGenerator
1-O-Myristoyl-sn-glycerol 3-phosphoric acidGenerator
1-O-Tetradecanoyl-sn-glycerol 3-phosphoric acidGenerator
1-Tetradecanoyl-sn-glycerol 3-phosphoric acidGenerator
1-Tetradecanoylglycerol 3-phosphoric acidGenerator
Myristoyl lysophosphatidateGenerator
1-Tetradecanoyl-sn-glycero-3-phosphoric acidGenerator
Chemical FormulaC17H35O7P
Average Molecular Weight382.4294
Monoisotopic Molecular Weight382.212039986
IUPAC Name[(2R)-2-hydroxy-3-(tetradecanoyloxy)propoxy]phosphonic acid
Traditional Name1-myristoyl lpa
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(O)(O)=O
InChI Identifier
InChI=1S/C17H35O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-17(19)23-14-16(18)15-24-25(20,21)22/h16,18H,2-15H2,1H3,(H2,20,21,22)/t16-/m1/s1
InChI KeyFAZBDRGXCKPVJU-MRXNPFEDSA-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 Descriptors
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.015 g/lALOGPS
LogP3.11ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP10(3.11) g/LALOGPS
logP10(4.07) g/LChemAxon
logS10(-4.4) g/LALOGPS
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 Count18ChemAxon
Refractivity95.78 m³·mol⁻¹ChemAxon
Polarizability42.9 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]+196.72231661259
DarkChem[M-H]-193.71531661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-tetradecanoyl-sn-glycero-3-phosphateCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(O)(O)=O3774.8Standard polar33892256
1-tetradecanoyl-sn-glycero-3-phosphateCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(O)(O)=O2551.5Standard non polar33892256
1-tetradecanoyl-sn-glycero-3-phosphateCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(O)(O)=O2904.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-tetradecanoyl-sn-glycero-3-phosphate,1TMS,isomer #1CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O)O[Si](C)(C)C2854.4Semi standard non polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,1TMS,isomer #2CCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)O[Si](C)(C)C2858.5Semi standard non polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,2TMS,isomer #1CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C2903.9Semi standard non polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,2TMS,isomer #1CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C2780.6Standard non polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,2TMS,isomer #1CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C3569.3Standard polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,2TMS,isomer #2CCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2922.2Semi standard non polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,2TMS,isomer #2CCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2788.4Standard non polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,2TMS,isomer #2CCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3256.7Standard polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,3TMS,isomer #1CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2924.9Semi standard non polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,3TMS,isomer #1CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2832.3Standard non polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,3TMS,isomer #1CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3089.0Standard polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,1TBDMS,isomer #1CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O)O[Si](C)(C)C(C)(C)C3104.6Semi standard non polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,1TBDMS,isomer #2CCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)O[Si](C)(C)C(C)(C)C3104.8Semi standard non polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,2TBDMS,isomer #1CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3378.8Semi standard non polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,2TBDMS,isomer #1CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3091.4Standard non polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,2TBDMS,isomer #1CCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3673.4Standard polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,2TBDMS,isomer #2CCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3367.5Semi standard non polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,2TBDMS,isomer #2CCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3078.5Standard non polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,2TBDMS,isomer #2CCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3443.2Standard polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,3TBDMS,isomer #1CCCCCCCCCCCCCC(=O)OC[C@H](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)C3623.9Semi standard non polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,3TBDMS,isomer #1CCCCCCCCCCCCCC(=O)OC[C@H](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)C3216.1Standard non polar33892256
1-tetradecanoyl-sn-glycero-3-phosphate,3TBDMS,isomer #1CCCCCCCCCCCCCC(=O)OC[C@H](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)C3318.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-tetradecanoyl-sn-glycero-3-phosphate GC-MS (1 TMS) - 70eV, Positivesplash10-01r2-9430000000-f861d93c20ee8e406d562017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-tetradecanoyl-sn-glycero-3-phosphate 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-tetradecanoyl-sn-glycero-3-phosphate 10V, Negative-QTOFsplash10-001i-0009000000-0cf40b8b7adbde49f5802021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-tetradecanoyl-sn-glycero-3-phosphate 20V, Negative-QTOFsplash10-001i-0009000000-0cf40b8b7adbde49f5802021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-tetradecanoyl-sn-glycero-3-phosphate 40V, Negative-QTOFsplash10-0ugi-2956000000-1e1f2694e15d344f7ffa2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-tetradecanoyl-sn-glycero-3-phosphate 10V, Positive-QTOFsplash10-001i-0009000000-5d141a336820399612f52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-tetradecanoyl-sn-glycero-3-phosphate 20V, Positive-QTOFsplash10-001i-0009000000-5d141a336820399612f52021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-tetradecanoyl-sn-glycero-3-phosphate 40V, Positive-QTOFsplash10-02mi-0957000000-bb4d7a4c6e719d94ea812021-09-24Wishart 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 ID7826123
KEGG Compound IDNot Available
BioCyc IDCPD0-2254
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound9547180
PDB IDNKN
ChEBI ID62833
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.