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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-16 03:42:48 UTC
Update Date2022-03-07 03:17:52 UTC
HMDB IDHMDB0062317
Secondary Accession Numbers
  • HMDB62317
Metabolite Identification
Common Name1-heneicosanoyl-glycero-3-phosphate
DescriptionPA(21:0/0:0)is a phosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidic acids can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. Fatty acids containing 16, 18 and 20 carbons are the most common. PA(21:0/0:0), in particular, consists of two heneicosanoyl chain at positions C-1 and C2. The oleic acid moiety is derived from vegetable oils, especially olive and canola oil, while the oleic acid moiety is derived from vegetable oils, especially olive and canola oil. Phosphatidic acids are quite rare but are extremely important as intermediates in the biosynthesis of triacylglycerols and phospholipids.
Structure
Data?1563866295
Synonyms
ValueSource
1-Heneicosanoyl-glycero-3-phosphoric acidGenerator
Chemical FormulaC24H49O7P
Average Molecular Weight480.623
Monoisotopic Molecular Weight480.321590916
IUPAC Name[(2R)-3-(henicosanoyloxy)-2-hydroxypropoxy]phosphonic acid
Traditional Name(2R)-3-(henicosanoyloxy)-2-hydroxypropoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCCCCC)COP(O)(O)=O
InChI Identifier
InChI=1S/C24H49O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-24(26)30-21-23(25)22-31-32(27,28)29/h23,25H,2-22H2,1H3,(H2,27,28,29)/t23-/m1/s1
InChI KeySPXKINNONQHLLM-HSZRJFAPSA-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
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00081 g/lALOGPS
LogP6.13ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP6.13ALOGPS
logP7.18ChemAxon
logS-5.8ALOGPS
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 Count25ChemAxon
Refractivity127.99 m³·mol⁻¹ChemAxon
Polarizability57.92 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+223.48631661259
DarkChem[M-H]-219.46231661259
DeepCCS[M+H]+203.89630932474
DeepCCS[M-H]-201.53830932474
DeepCCS[M-2H]-234.42830932474
DeepCCS[M+Na]+209.98930932474
AllCCS[M+H]+228.532859911
AllCCS[M+H-H2O]+226.932859911
AllCCS[M+NH4]+230.032859911
AllCCS[M+Na]+230.532859911
AllCCS[M-H]-218.332859911
AllCCS[M+Na-2H]-221.232859911
AllCCS[M+HCOO]-224.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-heneicosanoyl-glycero-3-phosphate[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCCCCC)COP(O)(O)=O3746.5Standard polar33892256
1-heneicosanoyl-glycero-3-phosphate[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCCCCC)COP(O)(O)=O3181.5Standard non polar33892256
1-heneicosanoyl-glycero-3-phosphate[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCCCCCC)COP(O)(O)=O3626.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-heneicosanoyl-glycero-3-phosphate,1TMS,isomer #1CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O)O[Si](C)(C)C3582.0Semi standard non polar33892256
1-heneicosanoyl-glycero-3-phosphate,1TMS,isomer #2CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)O[Si](C)(C)C3575.6Semi standard non polar33892256
1-heneicosanoyl-glycero-3-phosphate,2TMS,isomer #1CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C3577.1Semi standard non polar33892256
1-heneicosanoyl-glycero-3-phosphate,2TMS,isomer #1CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C3384.2Standard non polar33892256
1-heneicosanoyl-glycero-3-phosphate,2TMS,isomer #1CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C4283.7Standard polar33892256
1-heneicosanoyl-glycero-3-phosphate,2TMS,isomer #2CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3575.2Semi standard non polar33892256
1-heneicosanoyl-glycero-3-phosphate,2TMS,isomer #2CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3408.6Standard non polar33892256
1-heneicosanoyl-glycero-3-phosphate,2TMS,isomer #2CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3932.0Standard polar33892256
1-heneicosanoyl-glycero-3-phosphate,3TMS,isomer #1CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3598.3Semi standard non polar33892256
1-heneicosanoyl-glycero-3-phosphate,3TMS,isomer #1CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3408.0Standard non polar33892256
1-heneicosanoyl-glycero-3-phosphate,3TMS,isomer #1CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3717.4Standard polar33892256
1-heneicosanoyl-glycero-3-phosphate,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O)O[Si](C)(C)C(C)(C)C3840.5Semi standard non polar33892256
1-heneicosanoyl-glycero-3-phosphate,1TBDMS,isomer #2CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)O[Si](C)(C)C(C)(C)C3823.9Semi standard non polar33892256
1-heneicosanoyl-glycero-3-phosphate,2TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4079.6Semi standard non polar33892256
1-heneicosanoyl-glycero-3-phosphate,2TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3654.2Standard non polar33892256
1-heneicosanoyl-glycero-3-phosphate,2TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4304.9Standard polar33892256
1-heneicosanoyl-glycero-3-phosphate,2TBDMS,isomer #2CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4055.9Semi standard non polar33892256
1-heneicosanoyl-glycero-3-phosphate,2TBDMS,isomer #2CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3644.0Standard non polar33892256
1-heneicosanoyl-glycero-3-phosphate,2TBDMS,isomer #2CCCCCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4062.9Standard polar33892256
1-heneicosanoyl-glycero-3-phosphate,3TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCC(=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)C4310.4Semi standard non polar33892256
1-heneicosanoyl-glycero-3-phosphate,3TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCC(=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)C3770.2Standard non polar33892256
1-heneicosanoyl-glycero-3-phosphate,3TBDMS,isomer #1CCCCCCCCCCCCCCCCCCCCC(=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)C3901.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-heneicosanoyl-glycero-3-phosphate GC-MS (1 TMS) - 70eV, Positivesplash10-01ot-9430000000-eff32c44351e34efd3872017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-heneicosanoyl-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-heneicosanoyl-glycero-3-phosphate 10V, Negative-QTOFsplash10-004i-0000900000-024f0a985b4b5a0e97b32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-heneicosanoyl-glycero-3-phosphate 20V, Negative-QTOFsplash10-004i-0000900000-024f0a985b4b5a0e97b32021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-heneicosanoyl-glycero-3-phosphate 40V, Negative-QTOFsplash10-0fb9-2905600000-f8c356f5d64b8cc1390a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-heneicosanoyl-glycero-3-phosphate 10V, Positive-QTOFsplash10-001i-0000900000-1760e2edd0efa4e6eafe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-heneicosanoyl-glycero-3-phosphate 20V, Positive-QTOFsplash10-001i-0000900000-1760e2edd0efa4e6eafe2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-heneicosanoyl-glycero-3-phosphate 40V, Positive-QTOFsplash10-074i-0905700000-f9ce067e1b9cd42c19ab2021-09-22Wishart 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 Compound52929764
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.