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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2014-04-16 20:45:58 UTC
Update Date2021-09-14 15:42:31 UTC
HMDB IDHMDB0061697
Secondary Accession Numbers
  • HMDB61697
Metabolite Identification
Common Name1-Stearoylglycerophosphoglycerol
Description1-Stearoylglycerophosphoglycerol is a phosphatidylglycerol. It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached at the C-1 and C-2 positions. PG(18:0/0:0), in particular, consists of two octadecanoyl chains at positions C-1 and C-2. In E. coli glycerophospholipid metabolism, phosphatidylglycerol is formed from phosphatidic acid (1,2-diacyl-sn-glycerol 3-phosphate) by a sequence of enzymatic reactions that proceeds via two intermediates, cytidine diphosphate diacylglycerol (CDP-diacylglycerol) and phosphatidylglycerophosphate (PGP, a phosphorylated phosphatidylglycerol). Phosphatidylglycerols, along with CDP-diacylglycerol, also serve as precursor molecules for the synthesis of cardiolipin, a phospholipid found in membranes.
Structure
Data?1563866221
SynonymsNot Available
Chemical FormulaC24H49O9P
Average Molecular Weight512.6142
Monoisotopic Molecular Weight512.311419678
IUPAC Name(2,3-dihydroxypropoxy)[2-hydroxy-3-(octadecanoyloxy)propoxy]phosphinic acid
Traditional Name2,3-dihydroxypropoxy(2-hydroxy-3-(octadecanoyloxy)propoxy)phosphinic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(O)(=O)OCC(O)CO
InChI Identifier
InChI=1S/C24H49O9P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-24(28)31-19-23(27)21-33-34(29,30)32-20-22(26)18-25/h22-23,25-27H,2-21H2,1H3,(H,29,30)
InChI KeyHFJVKBVEKQHVTO-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as lysophosphatidylglycerols. These are glycerophosphoglycerols (molecules containing a glycerol moiety attached to the phosphate group linked to a glycerol) in which only one fatty acid is bonded to the 1-glycerol moiety (through an ester linkage).
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoglycerols
Direct ParentLysophosphatidylglycerols
Alternative Parents
Substituents
  • Monoacylglycerophosphoglycerol
  • Fatty acid ester
  • Dialkyl phosphate
  • Organic phosphoric acid derivative
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Carboxylic acid ester
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Primary alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Physical Properties
StateNot Available
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
Water Solubility0.0012 g/LALOGPS
logP4.02ALOGPS
logP4.91ChemAxon
logS-5.6ALOGPS
pKa (Strongest Acidic)1.89ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area142.75 ŲChemAxon
Rotatable Bond Count26ChemAxon
Refractivity130.92 m³·mol⁻¹ChemAxon
Polarizability59.13 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]+226.75931661259
DarkChem[M-H]-221.38431661259
DeepCCS[M+H]+210.13430932474
DeepCCS[M-H]-206.11430932474
DeepCCS[M-2H]-242.65630932474
DeepCCS[M+Na]+218.94930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
1-StearoylglycerophosphoglycerolCCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(O)(=O)OCC(O)CO3819.7Standard polar33892256
1-StearoylglycerophosphoglycerolCCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(O)(=O)OCC(O)CO3326.0Standard non polar33892256
1-StearoylglycerophosphoglycerolCCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(O)(=O)OCC(O)CO3783.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
1-Stearoylglycerophosphoglycerol,1TMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC(O)CO)O[Si](C)(C)C3854.7Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,1TMS,isomer #2CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(O)OCC(CO)O[Si](C)(C)C3821.3Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,1TMS,isomer #3CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(O)OCC(O)CO[Si](C)(C)C3837.4Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,1TMS,isomer #4CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(OCC(O)CO)O[Si](C)(C)C3824.7Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,2TMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC(CO)O[Si](C)(C)C)O[Si](C)(C)C3780.5Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,2TMS,isomer #2CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC(O)CO[Si](C)(C)C)O[Si](C)(C)C3785.6Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,2TMS,isomer #3CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(OCC(O)CO)O[Si](C)(C)C)O[Si](C)(C)C3801.4Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,2TMS,isomer #4CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(O)OCC(CO[Si](C)(C)C)O[Si](C)(C)C3788.8Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,2TMS,isomer #5CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(OCC(CO)O[Si](C)(C)C)O[Si](C)(C)C3788.2Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,2TMS,isomer #6CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(OCC(O)CO[Si](C)(C)C)O[Si](C)(C)C3800.9Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,3TMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC(CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3772.1Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,3TMS,isomer #2CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(OCC(CO)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3773.7Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,3TMS,isomer #3CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(OCC(O)CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3772.3Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,3TMS,isomer #4CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(OCC(CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3777.1Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,4TMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(OCC(CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3760.1Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,4TMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(OCC(CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3473.6Standard non polar33892256
1-Stearoylglycerophosphoglycerol,4TMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(OCC(CO[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C3946.3Standard polar33892256
1-Stearoylglycerophosphoglycerol,1TBDMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC(O)CO)O[Si](C)(C)C(C)(C)C4102.5Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,1TBDMS,isomer #2CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(O)OCC(CO)O[Si](C)(C)C(C)(C)C4064.2Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,1TBDMS,isomer #3CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(O)OCC(O)CO[Si](C)(C)C(C)(C)C4083.6Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,1TBDMS,isomer #4CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(OCC(O)CO)O[Si](C)(C)C(C)(C)C4050.2Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,2TBDMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC(CO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4294.1Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,2TBDMS,isomer #2CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC(O)CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4289.9Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,2TBDMS,isomer #3CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(OCC(O)CO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4283.6Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,2TBDMS,isomer #4CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(O)OCC(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4295.9Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,2TBDMS,isomer #5CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(OCC(CO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4250.5Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,2TBDMS,isomer #6CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(OCC(O)CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4244.0Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,3TBDMS,isomer #1CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(O)OCC(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4518.7Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,3TBDMS,isomer #2CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(OCC(CO)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4471.6Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,3TBDMS,isomer #3CCCCCCCCCCCCCCCCCC(=O)OCC(COP(=O)(OCC(O)CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4462.0Semi standard non polar33892256
1-Stearoylglycerophosphoglycerol,3TBDMS,isomer #4CCCCCCCCCCCCCCCCCC(=O)OCC(O)COP(=O)(OCC(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4466.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 1-Stearoylglycerophosphoglycerol GC-MS (Non-derivatized) - 70eV, Positivesplash10-01pa-4940400000-b3025a16259a9800020d2017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 1-Stearoylglycerophosphoglycerol GC-MS (2 TMS) - 70eV, Positivesplash10-0006-3291035000-f08e8ed07c19d70293b12017-10-06Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Stearoylglycerophosphoglycerol 10V, Positive-QTOFsplash10-07fs-6293540000-160bab5f977b7291bd6e2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Stearoylglycerophosphoglycerol 20V, Positive-QTOFsplash10-05r0-9382200000-98f2ced18cc9da5e01112017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Stearoylglycerophosphoglycerol 40V, Positive-QTOFsplash10-0a6r-9241000000-5c02061344195b9fb3a22017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Stearoylglycerophosphoglycerol 10V, Negative-QTOFsplash10-02ai-0190220000-2591143d742752de627a2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Stearoylglycerophosphoglycerol 20V, Negative-QTOFsplash10-00pi-5390100000-2f52829519e708d8e8582017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Stearoylglycerophosphoglycerol 40V, Negative-QTOFsplash10-004i-9110000000-ce5978124d83286d2aab2017-10-06Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Stearoylglycerophosphoglycerol 10V, Negative-QTOFsplash10-03di-0000090000-dacfb23d9b1367d2d7f12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Stearoylglycerophosphoglycerol 20V, Negative-QTOFsplash10-03di-0000090000-dacfb23d9b1367d2d7f12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 1-Stearoylglycerophosphoglycerol 40V, Negative-QTOFsplash10-03f0-0190260000-3de25b01664acdff86c42021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
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 Compound10029397
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. 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.