Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-16 03:42:51 UTC
Update Date2022-03-07 03:17:52 UTC
HMDB IDHMDB0062318
Secondary Accession Numbers
  • HMDB62318
Metabolite Identification
Common Name1-heptadecanoyl-glycero-3-phosphate
Description1-heptadecanoyl-glycero-3-phosphate, also known as PA(17:0/0:0), is classified as a member of the 1-acylglycerol-3-phosphates. 1-acylglycerol-3-phosphates are lysophosphatidic acids where the glycerol is esterified with a fatty acid at O-1 position. 1-heptadecanoyl-glycero-3-phosphate is considered to be practically insoluble (in water) and acidic. 1-heptadecanoyl-glycero-3-phosphate is a glycerophosphate lipid molecule
Structure
Data?1563866295
Synonyms
ValueSource
1-Heptadecanoylglycero-3-phosphateChEBI
PA(17:0/0:0)ChEBI
1-Heptadecanoylglycero-3-phosphoric acidGenerator
1-Heptadecanoyl-sn-glycero-3-phosphoric acidGenerator
1-Heptadecanoyl-glycero-3-phosphoric acidGenerator
Chemical FormulaC20H41O7P
Average Molecular Weight424.515
Monoisotopic Molecular Weight424.258990658
IUPAC Name[(2R)-3-(heptadecanoyloxy)-2-hydroxypropoxy]phosphonic acid
Traditional Name(2R)-3-(heptadecanoyloxy)-2-hydroxypropoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCC)COP(O)(O)=O
InChI Identifier
InChI=1S/C20H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-20(22)26-17-19(21)18-27-28(23,24)25/h19,21H,2-18H2,1H3,(H2,23,24,25)/t19-/m1/s1
InChI KeyAXKVUJMUBAXXKG-LJQANCHMSA-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
Physiological effectNot Available
DispositionNot Available
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0018 g/lALOGPS
LogP4.52ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP4.52ALOGPS
logP5.4ChemAxon
logS-5.4ALOGPS
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 Count21ChemAxon
Refractivity109.58 m³·mol⁻¹ChemAxon
Polarizability49.32 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
DarkChem[M+H]+208.14431661259
DarkChem[M-H]-204.28731661259
DeepCCS[M+H]+188.45530932474
DeepCCS[M-H]-186.09730932474
DeepCCS[M-2H]-219.18330932474
DeepCCS[M+Na]+194.54830932474
AllCCS[M+H]+210.532859911
AllCCS[M+H-H2O]+208.532859911
AllCCS[M+NH4]+212.332859911
AllCCS[M+Na]+212.932859911
AllCCS[M-H]-204.432859911
AllCCS[M+Na-2H]-206.432859911
AllCCS[M+HCOO]-208.832859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-heptadecanoyl-glycero-3-phosphate[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCC)COP(O)(O)=O3782.2Standard polar33892256
1-heptadecanoyl-glycero-3-phosphate[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCC)COP(O)(O)=O2829.9Standard non polar33892256
1-heptadecanoyl-glycero-3-phosphate[H][C@@](O)(COC(=O)CCCCCCCCCCCCCCCC)COP(O)(O)=O3207.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-heptadecanoyl-glycero-3-phosphate,1TMS,isomer #1CCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O)O[Si](C)(C)C3159.5Semi standard non polar33892256
1-heptadecanoyl-glycero-3-phosphate,1TMS,isomer #2CCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)O[Si](C)(C)C3165.2Semi standard non polar33892256
1-heptadecanoyl-glycero-3-phosphate,2TMS,isomer #1CCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C3191.5Semi standard non polar33892256
1-heptadecanoyl-glycero-3-phosphate,2TMS,isomer #1CCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C3042.1Standard non polar33892256
1-heptadecanoyl-glycero-3-phosphate,2TMS,isomer #1CCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C3877.0Standard polar33892256
1-heptadecanoyl-glycero-3-phosphate,2TMS,isomer #2CCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3202.0Semi standard non polar33892256
1-heptadecanoyl-glycero-3-phosphate,2TMS,isomer #2CCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3055.8Standard non polar33892256
1-heptadecanoyl-glycero-3-phosphate,2TMS,isomer #2CCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3550.7Standard polar33892256
1-heptadecanoyl-glycero-3-phosphate,3TMS,isomer #1CCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3214.0Semi standard non polar33892256
1-heptadecanoyl-glycero-3-phosphate,3TMS,isomer #1CCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3082.1Standard non polar33892256
1-heptadecanoyl-glycero-3-phosphate,3TMS,isomer #1CCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3359.0Standard polar33892256
1-heptadecanoyl-glycero-3-phosphate,1TBDMS,isomer #1CCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O)O[Si](C)(C)C(C)(C)C3418.4Semi standard non polar33892256
1-heptadecanoyl-glycero-3-phosphate,1TBDMS,isomer #2CCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O)O[Si](C)(C)C(C)(C)C3411.9Semi standard non polar33892256
1-heptadecanoyl-glycero-3-phosphate,2TBDMS,isomer #1CCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3678.8Semi standard non polar33892256
1-heptadecanoyl-glycero-3-phosphate,2TBDMS,isomer #1CCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3333.6Standard non polar33892256
1-heptadecanoyl-glycero-3-phosphate,2TBDMS,isomer #1CCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3945.3Standard polar33892256
1-heptadecanoyl-glycero-3-phosphate,2TBDMS,isomer #2CCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3659.4Semi standard non polar33892256
1-heptadecanoyl-glycero-3-phosphate,2TBDMS,isomer #2CCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3321.6Standard non polar33892256
1-heptadecanoyl-glycero-3-phosphate,2TBDMS,isomer #2CCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3710.7Standard polar33892256
1-heptadecanoyl-glycero-3-phosphate,3TBDMS,isomer #1CCCCCCCCCCCCCCCCC(=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)C3918.8Semi standard non polar33892256
1-heptadecanoyl-glycero-3-phosphate,3TBDMS,isomer #1CCCCCCCCCCCCCCCCC(=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)C3453.2Standard non polar33892256
1-heptadecanoyl-glycero-3-phosphate,3TBDMS,isomer #1CCCCCCCCCCCCCCCCC(=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)C3566.3Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-heptadecanoyl-glycero-3-phosphate GC-MS (1 TMS) - 70eV, Positivesplash10-01r2-9430000000-51c0e701cf26328925fd2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-heptadecanoyl-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-heptadecanoyl-glycero-3-phosphate 10V, Positive-QTOFsplash10-004i-0000900000-646ca740f0200fe8b6c12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-heptadecanoyl-glycero-3-phosphate 20V, Positive-QTOFsplash10-004i-0000900000-646ca740f0200fe8b6c12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-heptadecanoyl-glycero-3-phosphate 40V, Positive-QTOFsplash10-0kmi-0950700000-a92d792a7f6f963c54712021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-heptadecanoyl-glycero-3-phosphate 10V, Negative-QTOFsplash10-00di-0000900000-c45058665348c78e8ee72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-heptadecanoyl-glycero-3-phosphate 20V, Negative-QTOFsplash10-00di-0000900000-c45058665348c78e8ee72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-heptadecanoyl-glycero-3-phosphate 40V, Negative-QTOFsplash10-0v4i-2950600000-b5bf8d4314e8e63ad5f12021-09-23Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)2022-08-20Wishart 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 Compound44575057
PDB IDNot Available
ChEBI ID74840
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.