Record Information |
---|
Version | 4.0 |
---|
Status | Detected but not Quantified |
---|
Creation Date | 2014-04-16 20:45:51 UTC |
---|
Update Date | 2020-11-09 23:21:59 UTC |
---|
HMDB ID | HMDB0061695 |
---|
Secondary Accession Numbers | - HMDB0062714
- HMDB61695
- HMDB62714
|
---|
Metabolite Identification |
---|
Common Name | LysoPI(16:0/0:0) |
---|
Description | LysoPI(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 | |
---|
Synonyms | Value | Source |
---|
1-Hexadecanoyl-sn-glycero-3-phospho-(1'-myo-inositol) | ChEBI | 1-Palmitoyl-sn--glycero-3-phospho-D-myo-inositol | ChEBI | PI(16:0/0:0) | ChEBI | 1-Palmitoylglycerophosphoinositol | ChEBI | 1-Palmitoyl-3-glycerylphosphorylinositol | HMDB | 1-Palmitoyl-GPI | HMDB | 1-Palmitoyl-glycero-3-phospho-(1'-myo-inositol) | HMDB | 1-Palmitoyl-glycero-3-phospho-(1’-myo-inositol) | HMDB | 1-Palmitoyl-lysophosphatidylinositol | HMDB | 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 | Palmitoyllysophosphatidylinositol | HMDB | 1-Palmitoyl-sn-glycero-3-phospho-D-myo-inositol | HMDB |
|
---|
Chemical Formula | C25H49O12P |
---|
Average Molecular Weight | 572.6231 |
---|
Monoisotopic Molecular Weight | 572.296163544 |
---|
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 Number | 1425501-12-7 |
---|
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 Key | UOXRPRZMAROFPH-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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Glycerophospholipids |
---|
Sub Class | Glycerophosphoinositols |
---|
Direct Parent | 1-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 Framework | Aliphatic homomonocyclic compounds |
---|
External Descriptors | - 1-acyl-sn-glycero-3-phospho-1D-myo-inositol (CHEBI:73218 )
|
---|
Ontology |
---|
|
Physiological effect | Organoleptic effect: |
---|
Disposition | Route of exposure: Source: Biological location: |
---|
Process | Naturally occurring process: |
---|
Role | Biological role: Industrial application: |
---|
Physical Properties |
---|
State | Not Available |
---|
Experimental Properties | Property | Value | Reference |
---|
Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
|
---|
Predicted Properties | |
---|
| Spectrum Type | Description | Splash Key | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0nmi-5595660000-d2cf621f8764e7cd5c41 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-03g0-8591325000-1ceabd2ae42c849f19bd | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-08mr-1587290000-a818d4c05fd0231239d8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0bti-2294010000-7ebb451b4e5751fbed89 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-03di-6921000000-d09ceae851b37dabddda | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0abi-0092040000-9d4b675d2bec007e0cea | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-3191010000-fbcb12c131a1edd750a6 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9030000000-3e7cb30ab77ff62e3afd | Spectrum |
|
---|
General References | - Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
- Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
- 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 ]
- 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 ]
- 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 ]
- 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 ]
- Cevc, Gregor (1993). Phospholipids Handbook. Marcel Dekker.
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
|
---|