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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2014-04-16 20:45:51 UTC
Update Date2019-03-14 18:05:57 UTC
HMDB IDHMDB0061695
Secondary Accession Numbers
  • HMDB61695
Metabolite Identification
Common Name1-Palmitoylglycerophosphoinositol
Description1-Palmitoylglycerophosphoinositol belongs to the family of glycerophosphoinositols, which are lipids containing a common glycerophosphate skeleton linked to at least one fatty acyl chain and an inositol moiety. Their general formula is O[C@H]1[C@H](O)[C@@H](O)[C@H](OP(O)(=O)OC[C@@H](CO(R1))O(R2))[C@H](O)[C@@H]1O, where R1-R2 are fatty acid chains PI(16:0/0:0) is made up of one hexadecanoyl(R1).
Structure
Data?1549929456
Synonyms
ValueSource
1-Hexadecanoyl-sn-glycero-3-phospho-(1'-myo-inositol)ChEBI
1-Palmitoyl-sn--glycero-3-phospho-D-myo-inositolChEBI
1-PalmitoylglycerophosphoinositolChEBI
PI(16:0/0:0)ChEBI
Chemical FormulaC25H49O12P
Average Molecular Weight572.6231
Monoisotopic Molecular Weight572.296163544
IUPAC Name[(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy]({[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxy})phosphinic acid
Traditional Name(2R)-3-(hexadecanoyloxy)-2-hydroxypropoxy[(1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]oxyphosphinic acid
CAS Registry NumberNot Available
SMILES
CCCCCCCCCCCCCCCC(=O)OC[C@@H](O)COP(O)(=O)O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C25H49O12P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(27)35-16-18(26)17-36-38(33,34)37-25-23(31)21(29)20(28)22(30)24(25)32/h18,20-26,28-32H,2-17H2,1H3,(H,33,34)/t18-,20-,21-,22+,23-,24-,25-/m1/s1
InChI KeyUOXRPRZMAROFPH-OAOCPRPWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 1-acyl-sn-glycerol-3-phosphoinositols. These are glycerophosphoinositols where the glycerol is acylated only at position O-1 with a fatty acid.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerophospholipids
Sub ClassGlycerophosphoinositols
Direct Parent1-acyl-sn-glycerol-3-phosphoinositols
Alternative Parents
Substituents
  • 1-acyl-sn-glycerol-3-phosphoinositol
  • Inositol phosphate
  • Dialkyl phosphate
  • Cyclohexanol
  • Fatty acid ester
  • Cyclitol or derivatives
  • Fatty acyl
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Cyclic alcohol
  • Carboxylic acid ester
  • Secondary alcohol
  • Carboxylic acid derivative
  • Polyol
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Carbonyl group
  • Organic oxide
  • Alcohol
  • Organooxygen compound
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Organoleptic effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Industrial application:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
logP2.31ALOGPS
logP2.07ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)1.83ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area203.44 ŲChemAxon
Rotatable Bond Count22ChemAxon
Refractivity136.98 m³·mol⁻¹ChemAxon
Polarizability62.29 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0nmi-5595660000-d2cf621f8764e7cd5c41JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03g0-8591325000-1ceabd2ae42c849f19bdJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08mr-1587290000-a818d4c05fd0231239d8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bti-2294010000-7ebb451b4e5751fbed89JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-6921000000-d09ceae851b37dabdddaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0abi-0092040000-9d4b675d2bec007e0ceaJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-3191010000-fbcb12c131a1edd750a6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9030000000-3e7cb30ab77ff62e3afdJSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB 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 CompoundNot Available
PDB IDNot Available
ChEBI ID73218
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.