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Showing metabocard for LysoPI(16:0/0:0) (HMDB0061695)

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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2014-04-16 20:45:51 UTC
Update Date2020-02-26 19:17:41 UTC
HMDB IDHMDB0061695
Secondary Accession Numbers
  • HMDB0062714
  • HMDB61695
  • HMDB62714
Metabolite Identification
Common NameLysoPI(16:0/0:0)
DescriptionLysoPI(16:0/0:0) is a lysophosphatidylinositol. The term 'lysophospholipid' (LPL) refers to any phospholipid that is missing one of its two O-acyl chains. Thus, LPLs have a free alcohol in either the sn-1 or sn-2 position. The prefix 'lyso-' comes from the fact that lysophospholipids were originally found to be hemolytic. However, it is now used to refer generally to phospholipids missing an acyl chain. LPLs are usually the result of phospholipase A-type enzymatic activity on regular phospholipids such as phosphatidylcholine or phosphatidic acid, although they can also be generated by the acylation of glycerophospholipids or the phosphorylation of monoacylglycerols. Lysophosphatidylinositols can have different combinations of fatty acids of varying lengths and saturation attached at the C-1 (sn-1) or C-2 (sn-2) position. LysoPI(16:0/0:0), in particular, consists of one chain of palmitic acid at the C-1 position.
Structure
Data?1573234062
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-Hexadecanoyl-sn-glycero-3-phospho-(1'-myo-inositol)ChEBI
1-Palmitoyl-sn--glycero-3-phospho-D-myo-inositolChEBI
PI(16:0/0:0)ChEBI
1-PalmitoylglycerophosphoinositolChEBI
1-Palmitoyl-3-glycerylphosphorylinositolHMDB
1-Palmitoyl-GPIHMDB
1-Palmitoyl-glycero-3-phospho-(1'-myo-inositol)HMDB
1-Palmitoyl-glycero-3-phospho-(1’-myo-inositol)HMDB
1-Palmitoyl-lysophosphatidylinositolHMDB
GPI(16:0)HMDB
GPI(16:0/0:0)HMDB
LPI(16:0)HMDB
LPI(16:0/0:0)HMDB
LysoPI(16:0)HMDB
LysoPI(16:0/0:0)HMDB
Lysophosphatidylinositol(16:0)HMDB
Lysophosphatidylinositol(16:0/0:0)HMDB
PalmitoyllysophosphatidylinositolHMDB
1-Palmitoyl-sn-glycero-3-phospho-D-myo-inositolHMDB
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]oxy)phosphinic acid
CAS Registry Number1425501-12-7
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
Description 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
Polarizability62.28 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0nmi-5595660000-d2cf621f8764e7cd5c41Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-03g0-8591325000-1ceabd2ae42c849f19bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08mr-1587290000-a818d4c05fd0231239d8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bti-2294010000-7ebb451b4e5751fbed89Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03di-6921000000-d09ceae851b37dabdddaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0abi-0092040000-9d4b675d2bec007e0ceaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-3191010000-fbcb12c131a1edd750a6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9030000000-3e7cb30ab77ff62e3afdSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue Locations
  • Placenta
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
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
  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. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  7. Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.