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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2017-03-16 03:43:38 UTC
Update Date2022-03-07 03:17:53 UTC
HMDB IDHMDB0062325
Secondary Accession Numbers
  • HMDB62325
Metabolite Identification
Common Name1-hexadecyl-glycero-3-phosphate
Description1-hexadecyl-sn-glycerol 3-phosphate, also known as PA(O-16:0/0:0), belongs to the class of organic compounds known as monoalkylglycerophosphates. Monoalkylglycerophosphates are compounds containing glycerophosphate moiety attached to an fatty acyl chain through an ether bond. 1-hexadecyl-sn-glycerol 3-phosphate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Data?1563866296
Synonyms
ValueSource
PA(O-16:0/0:0)ChEBI
1-Hexadecyl-sn-glycerol 3-phosphoric acidGenerator
1-Hexadecyl-glycero-3-phosphoric acidGenerator
Chemical FormulaC19H41O6P
Average Molecular Weight396.505
Monoisotopic Molecular Weight396.264076038
IUPAC Name[(2R)-3-(hexadecyloxy)-2-hydroxypropoxy]phosphonic acid
Traditional Name(2R)-3-(hexadecyloxy)-2-hydroxypropoxyphosphonic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(COCCCCCCCCCCCCCCCC)COP(O)(O)=O
InChI Identifier
InChI=1S/C19H41O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-24-17-19(20)18-25-26(21,22)23/h19-20H,2-18H2,1H3,(H2,21,22,23)/t19-/m1/s1
InChI KeyXLVRFPVHQPHXAA-LJQANCHMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monoalkylglycerophosphates. Monoalkylglycerophosphates are compounds containing glycerophosphate moiety attached to an fatty acyl chain through an ether bond.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphates
Direct ParentMonoalkylglycerophosphates
Alternative Parents
Substituents
  • Monoalkylglycerophosphate
  • Monoalkyl phosphate
  • Glycerol ether
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Secondary alcohol
  • Ether
  • Dialkyl ether
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • 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 Solubility0.0036 g/lALOGPS
LogP4.70ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP4.7ALOGPS
logP5.34ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)1.51ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area96.22 ŲChemAxon
Rotatable Bond Count20ChemAxon
Refractivity105.23 m³·mol⁻¹ChemAxon
Polarizability47.63 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]+200.30931661259
DarkChem[M-H]-197.64131661259
DeepCCS[M+H]+183.07430932474
DeepCCS[M-H]-180.71630932474
DeepCCS[M-2H]-213.75130932474
DeepCCS[M+Na]+189.16730932474
AllCCS[M+H]+204.132859911
AllCCS[M+H-H2O]+202.032859911
AllCCS[M+NH4]+206.132859911
AllCCS[M+Na]+206.732859911
AllCCS[M-H]-199.632859911
AllCCS[M+Na-2H]-201.432859911
AllCCS[M+HCOO]-203.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-hexadecyl-glycero-3-phosphate[H][C@@](O)(COCCCCCCCCCCCCCCCC)COP(O)(O)=O3584.2Standard polar33892256
1-hexadecyl-glycero-3-phosphate[H][C@@](O)(COCCCCCCCCCCCCCCCC)COP(O)(O)=O2696.4Standard non polar33892256
1-hexadecyl-glycero-3-phosphate[H][C@@](O)(COCCCCCCCCCCCCCCCC)COP(O)(O)=O3003.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-hexadecyl-glycero-3-phosphate,1TMS,isomer #1CCCCCCCCCCCCCCCCOC[C@H](COP(=O)(O)O)O[Si](C)(C)C2963.6Semi standard non polar33892256
1-hexadecyl-glycero-3-phosphate,1TMS,isomer #2CCCCCCCCCCCCCCCCOC[C@@H](O)COP(=O)(O)O[Si](C)(C)C2988.6Semi standard non polar33892256
1-hexadecyl-glycero-3-phosphate,2TMS,isomer #1CCCCCCCCCCCCCCCCOC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C2997.9Semi standard non polar33892256
1-hexadecyl-glycero-3-phosphate,2TMS,isomer #1CCCCCCCCCCCCCCCCOC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C2892.3Standard non polar33892256
1-hexadecyl-glycero-3-phosphate,2TMS,isomer #1CCCCCCCCCCCCCCCCOC[C@H](COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C3556.3Standard polar33892256
1-hexadecyl-glycero-3-phosphate,2TMS,isomer #2CCCCCCCCCCCCCCCCOC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3018.7Semi standard non polar33892256
1-hexadecyl-glycero-3-phosphate,2TMS,isomer #2CCCCCCCCCCCCCCCCOC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C2927.5Standard non polar33892256
1-hexadecyl-glycero-3-phosphate,2TMS,isomer #2CCCCCCCCCCCCCCCCOC[C@@H](O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C3255.8Standard polar33892256
1-hexadecyl-glycero-3-phosphate,3TMS,isomer #1CCCCCCCCCCCCCCCCOC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3020.0Semi standard non polar33892256
1-hexadecyl-glycero-3-phosphate,3TMS,isomer #1CCCCCCCCCCCCCCCCOC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C2936.7Standard non polar33892256
1-hexadecyl-glycero-3-phosphate,3TMS,isomer #1CCCCCCCCCCCCCCCCOC[C@H](COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3085.2Standard polar33892256
1-hexadecyl-glycero-3-phosphate,1TBDMS,isomer #1CCCCCCCCCCCCCCCCOC[C@H](COP(=O)(O)O)O[Si](C)(C)C(C)(C)C3223.9Semi standard non polar33892256
1-hexadecyl-glycero-3-phosphate,1TBDMS,isomer #2CCCCCCCCCCCCCCCCOC[C@@H](O)COP(=O)(O)O[Si](C)(C)C(C)(C)C3219.1Semi standard non polar33892256
1-hexadecyl-glycero-3-phosphate,2TBDMS,isomer #1CCCCCCCCCCCCCCCCOC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3476.0Semi standard non polar33892256
1-hexadecyl-glycero-3-phosphate,2TBDMS,isomer #1CCCCCCCCCCCCCCCCOC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3182.0Standard non polar33892256
1-hexadecyl-glycero-3-phosphate,2TBDMS,isomer #1CCCCCCCCCCCCCCCCOC[C@H](COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3646.2Standard polar33892256
1-hexadecyl-glycero-3-phosphate,2TBDMS,isomer #2CCCCCCCCCCCCCCCCOC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3460.4Semi standard non polar33892256
1-hexadecyl-glycero-3-phosphate,2TBDMS,isomer #2CCCCCCCCCCCCCCCCOC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3179.2Standard non polar33892256
1-hexadecyl-glycero-3-phosphate,2TBDMS,isomer #2CCCCCCCCCCCCCCCCOC[C@@H](O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3428.4Standard polar33892256
1-hexadecyl-glycero-3-phosphate,3TBDMS,isomer #1CCCCCCCCCCCCCCCCOC[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)C3713.5Semi standard non polar33892256
1-hexadecyl-glycero-3-phosphate,3TBDMS,isomer #1CCCCCCCCCCCCCCCCOC[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)C3307.7Standard non polar33892256
1-hexadecyl-glycero-3-phosphate,3TBDMS,isomer #1CCCCCCCCCCCCCCCCOC[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)C3312.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-hexadecyl-glycero-3-phosphate GC-MS (Non-derivatized) - 70eV, Positivesplash10-01ot-9740000000-295e1eb38211fb21be652017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-hexadecyl-glycero-3-phosphate GC-MS (1 TMS) - 70eV, Positivesplash10-03fr-9580000000-4388bbb797e6da86bd0d2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-hexadecyl-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-hexadecyl-glycero-3-phosphate 10V, Positive-QTOFsplash10-0002-2179000000-a884e1a92875a735694b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-hexadecyl-glycero-3-phosphate 20V, Positive-QTOFsplash10-002b-6391000000-2da10648873bcabf09b02017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-hexadecyl-glycero-3-phosphate 40V, Positive-QTOFsplash10-004i-8890000000-8b6a37a92891aa7741e22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-hexadecyl-glycero-3-phosphate 10V, Negative-QTOFsplash10-002b-6119000000-b0d52a00adf4edd790ee2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-hexadecyl-glycero-3-phosphate 20V, Negative-QTOFsplash10-004i-9000000000-93ed4c32951b17e5c0822017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-hexadecyl-glycero-3-phosphate 40V, Negative-QTOFsplash10-004i-9000000000-ce75d45a8d3355f1bd6b2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-hexadecyl-glycero-3-phosphate 10V, Negative-QTOFsplash10-0002-0009000000-729226b5ab8bb7b767782021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-hexadecyl-glycero-3-phosphate 20V, Negative-QTOFsplash10-004i-9002000000-ea3411f9c14c8c50e06c2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-hexadecyl-glycero-3-phosphate 40V, Negative-QTOFsplash10-004i-9000000000-a5e502a2627af2048a1f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-hexadecyl-glycero-3-phosphate 10V, Positive-QTOFsplash10-0002-2197000000-d2509456f15c7416e8482021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-hexadecyl-glycero-3-phosphate 20V, Positive-QTOFsplash10-002b-9273000000-87e898792c9a8cf260112021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-hexadecyl-glycero-3-phosphate 40V, Positive-QTOFsplash10-052b-9100000000-a96a8821eb12cfa1de752021-09-25Wishart 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 Compound11825433
PDB IDNot Available
ChEBI ID63818
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. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  6. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.