Record Information |
---|
Version | 5.0 |
---|
Status | Detected but not Quantified |
---|
Creation Date | 2008-10-29 14:20:21 UTC |
---|
Update Date | 2022-11-30 19:03:55 UTC |
---|
HMDB ID | HMDB0011144 |
---|
Secondary Accession Numbers | |
---|
Metabolite Identification |
---|
Common Name | LysoPA(O-18:0/0:0) |
---|
Description | LysoPA(O-18:0/0:0) is a lysophosphatidic acid. It is a glycerophospholipid in which a phosphate moiety occupies a glycerol substitution site. Lysophosphatidic acids 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. Fatty acids containing 16 and 18 carbons are the most common.LysoPA(O-18:0/0:0), in particular, consists of one octadecyl chain. Lysophosphatidic acid is the simplest possible glycerophospholipid. It is the biosynthetic precursor of phosphatidic acid. Although it is present at very low levels only in animal tissues, it is extremely important biologically, influencing many biochemical processes. |
---|
Structure | CCCCCCCCCCCCCCCCCCOCC(O)COP(O)(O)=O InChI=1S/C21H45O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-26-19-21(22)20-27-28(23,24)25/h21-22H,2-20H2,1H3,(H2,23,24,25) |
---|
Synonyms | Value | Source |
---|
1-Octadecyl-sn-glycero-3-phosphate | HMDB | LysoPA(18:0E) | HMDB | LysoPA(O-18:0) | HMDB | PA(O-18:0/0:0) | HMDB | [(2R)-2-Hydroxy-3-octadecoxy-propyl] dihydrogen phosphate | HMDB | LPA(18:0E/0:0) | HMDB |
|
---|
Chemical Formula | C21H45O6P |
---|
Average Molecular Weight | 424.559 |
---|
Monoisotopic Molecular Weight | 424.295376167 |
---|
IUPAC Name | [2-hydroxy-3-(octadecyloxy)propoxy]phosphonic acid |
---|
Traditional Name | 2-hydroxy-3-(octadecyloxy)propoxyphosphonic acid |
---|
CAS Registry Number | Not Available |
---|
SMILES | CCCCCCCCCCCCCCCCCCOCC(O)COP(O)(O)=O |
---|
InChI Identifier | InChI=1S/C21H45O6P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-26-19-21(22)20-27-28(23,24)25/h21-22H,2-20H2,1H3,(H2,23,24,25) |
---|
InChI Key | HUUYDUFSUADEJQ-UHFFFAOYSA-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. |
---|
Kingdom | Organic compounds |
---|
Super Class | Lipids and lipid-like molecules |
---|
Class | Glycerophospholipids |
---|
Sub Class | Glycerophosphates |
---|
Direct Parent | Monoalkylglycerophosphates |
---|
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 Framework | Aliphatic acyclic compounds |
---|
External Descriptors | Not Available |
---|
Ontology |
---|
Not Available | Not Available |
---|
Physical Properties |
---|
State | Solid |
---|
Experimental Molecular 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 |
|
---|
Experimental Chromatographic Properties | Not Available |
---|
Predicted Molecular Properties | | Show more...
---|
Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
---|
LysoPA(O-18:0/0:0),1TMS,isomer #1 | CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O)O)O[Si](C)(C)C | 3250.7 | Semi standard non polar | 33892256 | LysoPA(O-18:0/0:0),1TMS,isomer #2 | CCCCCCCCCCCCCCCCCCOCC(O)COP(=O)(O)O[Si](C)(C)C | 3214.7 | Semi standard non polar | 33892256 | LysoPA(O-18:0/0:0),2TMS,isomer #1 | CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C | 3202.0 | Semi standard non polar | 33892256 | LysoPA(O-18:0/0:0),2TMS,isomer #1 | CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C | 3067.7 | Standard non polar | 33892256 | LysoPA(O-18:0/0:0),2TMS,isomer #1 | CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O)O[Si](C)(C)C)O[Si](C)(C)C | 3733.5 | Standard polar | 33892256 | LysoPA(O-18:0/0:0),2TMS,isomer #2 | CCCCCCCCCCCCCCCCCCOCC(O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 3215.6 | Semi standard non polar | 33892256 | LysoPA(O-18:0/0:0),2TMS,isomer #2 | CCCCCCCCCCCCCCCCCCOCC(O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 3099.4 | Standard non polar | 33892256 | LysoPA(O-18:0/0:0),2TMS,isomer #2 | CCCCCCCCCCCCCCCCCCOCC(O)COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C | 3442.2 | Standard polar | 33892256 | LysoPA(O-18:0/0:0),3TMS,isomer #1 | CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3216.8 | Semi standard non polar | 33892256 | LysoPA(O-18:0/0:0),3TMS,isomer #1 | CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3107.2 | Standard non polar | 33892256 | LysoPA(O-18:0/0:0),3TMS,isomer #1 | CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O[Si](C)(C)C)O[Si](C)(C)C)O[Si](C)(C)C | 3260.0 | Standard polar | 33892256 | LysoPA(O-18:0/0:0),1TBDMS,isomer #1 | CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O)O)O[Si](C)(C)C(C)(C)C | 3520.8 | Semi standard non polar | 33892256 | LysoPA(O-18:0/0:0),1TBDMS,isomer #2 | CCCCCCCCCCCCCCCCCCOCC(O)COP(=O)(O)O[Si](C)(C)C(C)(C)C | 3458.7 | Semi standard non polar | 33892256 | LysoPA(O-18:0/0:0),2TBDMS,isomer #1 | CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3685.0 | Semi standard non polar | 33892256 | LysoPA(O-18:0/0:0),2TBDMS,isomer #1 | CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3341.9 | Standard non polar | 33892256 | LysoPA(O-18:0/0:0),2TBDMS,isomer #1 | CCCCCCCCCCCCCCCCCCOCC(COP(=O)(O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3811.3 | Standard polar | 33892256 | LysoPA(O-18:0/0:0),2TBDMS,isomer #2 | CCCCCCCCCCCCCCCCCCOCC(O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3671.0 | Semi standard non polar | 33892256 | LysoPA(O-18:0/0:0),2TBDMS,isomer #2 | CCCCCCCCCCCCCCCCCCOCC(O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3328.1 | Standard non polar | 33892256 | LysoPA(O-18:0/0:0),2TBDMS,isomer #2 | CCCCCCCCCCCCCCCCCCOCC(O)COP(=O)(O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C | 3594.5 | Standard polar | 33892256 | LysoPA(O-18:0/0:0),3TBDMS,isomer #1 | CCCCCCCCCCCCCCCCCCOCC(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)C | 3910.9 | Semi standard non polar | 33892256 | LysoPA(O-18:0/0:0),3TBDMS,isomer #1 | CCCCCCCCCCCCCCCCCCOCC(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)C | 3482.5 | Standard non polar | 33892256 | LysoPA(O-18:0/0:0),3TBDMS,isomer #1 | CCCCCCCCCCCCCCCCCCOCC(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)C | 3469.9 | Standard polar | 33892256 |
| Show more...
---|
Spectra |
---|
| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted GC-MS | Predicted GC-MS Spectrum - LysoPA(O-18:0/0:0) GC-MS (1 TMS) - 70eV, Positive | splash10-03di-9470000000-767f506dcd3b43c89de4 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - LysoPA(O-18:0/0:0) GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
---|
Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 10V, Negative-QTOF | splash10-00fr-6110900000-8f719fedcd8fb1e4993c | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 20V, Negative-QTOF | splash10-004i-9000000000-0ea6133aa158799eba68 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 40V, Negative-QTOF | splash10-004i-9000000000-8f8d66131a6962c70022 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 10V, Negative-QTOF | splash10-00di-0000900000-ff350a6e4e4ad403170c | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 20V, Negative-QTOF | splash10-004i-9000100000-2f4e56c32a15bea85646 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 40V, Negative-QTOF | splash10-004i-9000000000-a5e502a2627af2048a1f | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 10V, Positive-QTOF | splash10-004i-2135900000-7c0ef85e3ad7588d5753 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 20V, Positive-QTOF | splash10-0zi1-9476200000-0b62a2b23bd2c2bd072f | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 40V, Positive-QTOF | splash10-0udi-8891000000-f8c957954f4425e7e3c4 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 10V, Positive-QTOF | splash10-004i-4105900000-6c1e7cdab36e3a134666 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 20V, Positive-QTOF | splash10-004i-9414200000-cd77a5ab324c3617b32a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - LysoPA(O-18:0/0:0) 40V, Positive-QTOF | splash10-052e-9100000000-586af9b8586d3135a523 | 2021-09-22 | Wishart Lab | View Spectrum |
| Show more...
---|
Biological Properties |
---|
Cellular Locations | |
---|
Biospecimen Locations | |
---|
Tissue Locations | Not Available |
---|
Pathways | |
---|
Normal Concentrations |
---|
| Not Available |
---|
Abnormal Concentrations |
---|
| |
Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Crohns disease | | details | Feces | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Iron deficiency | | details |
|
---|
Associated Disorders and Diseases |
---|
Disease References | Crohn's disease |
---|
- Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
| Iron deficiency |
---|
- Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
|
|
---|
Associated OMIM IDs | |
---|
External Links |
---|
DrugBank ID | Not Available |
---|
Phenol Explorer Compound ID | Not Available |
---|
FooDB ID | FDB098854 |
---|
KNApSAcK ID | Not Available |
---|
Chemspider ID | 16017852 |
---|
KEGG Compound ID | Not Available |
---|
BioCyc ID | Not Available |
---|
BiGG ID | Not Available |
---|
Wikipedia Link | Not Available |
---|
METLIN ID | Not Available |
---|
PubChem Compound | 12051354 |
---|
PDB ID | Not Available |
---|
ChEBI ID | Not Available |
---|
Food Biomarker Ontology | Not Available |
---|
VMH ID | Not Available |
---|
MarkerDB ID | Not Available |
---|
Good Scents ID | Not Available |
---|
References |
---|
Synthesis Reference | Not Available |
---|
Material Safety Data Sheet (MSDS) | Not Available |
---|
General References | - 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 ]
- Divecha N, Irvine RF: Phospholipid signaling. Cell. 1995 Jan 27;80(2):269-78. [PubMed:7834746 ]
- 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.
|
---|