Record Information |
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Version | 5.0 |
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Status | Detected and Quantified |
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Creation Date | 2012-09-08 15:00:03 UTC |
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Update Date | 2021-09-14 14:59:39 UTC |
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HMDB ID | HMDB0029216 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | SM C16:1 |
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Description | Sm c16:1 is classified as a member of the phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative. Sm c16:1 is considered to be a practically insoluble (in water) and a moderately acidic compound. Sm c16:1 can be found in blood and urine. Within a cell, Sm c16:1 is primarily located near the membrane (predicted from logp). |
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Structure | CCCCCCC\C=C\CCCCCCC[C@@H](O)[C@H](COP(O)(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCC\C=C\CCCCCC InChI=1S/C40H79N2O6P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-39(43)38(37-48-49(45,46)47-36-35-42(3,4)5)41-40(44)34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h17-20,38-39,43H,6-16,21-37H2,1-5H3,(H-,41,44,45,46)/p+1/b19-17+,20-18+/t38-,39+/m0/s1 |
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Synonyms | Not Available |
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Chemical Formula | C40H80N2O6P |
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Average Molecular Weight | 716.0468 |
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Monoisotopic Molecular Weight | 715.575399814 |
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IUPAC Name | {[(2S,3R,11E)-2-[(9E)-hexadec-9-enamido]-3-hydroxynonadec-11-en-1-yl]oxy}[2-(trimethylazaniumyl)ethoxy]phosphinic acid |
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Traditional Name | [(2S,3R,11E)-2-[(9E)-hexadec-9-enamido]-3-hydroxynonadec-11-en-1-yl]oxy(2-(trimethylammonio)ethoxy)phosphinic acid |
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CAS Registry Number | Not Available |
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SMILES | CCCCCCC\C=C\CCCCCCC[C@@H](O)[C@H](COP(O)(=O)OCC[N+](C)(C)C)NC(=O)CCCCCCC\C=C\CCCCCC |
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InChI Identifier | InChI=1S/C40H79N2O6P/c1-6-8-10-12-14-16-18-20-22-23-25-27-29-31-33-39(43)38(37-48-49(45,46)47-36-35-42(3,4)5)41-40(44)34-32-30-28-26-24-21-19-17-15-13-11-9-7-2/h17-20,38-39,43H,6-16,21-37H2,1-5H3,(H-,41,44,45,46)/p+1/b19-17+,20-18+/t38-,39+/m0/s1 |
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InChI Key | ZKIVREDSEABFBU-NDBDZNEVSA-O |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as phosphocholines. Phosphocholines are compounds containing a [2-(trimethylazaniumyl)ethoxy]phosphonic acid or derivative. |
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Kingdom | Organic compounds |
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Super Class | Organic nitrogen compounds |
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Class | Organonitrogen compounds |
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Sub Class | Quaternary ammonium salts |
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Direct Parent | Phosphocholines |
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Alternative Parents | |
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Substituents | - Phosphocholine
- Phosphoethanolamine
- Dialkyl phosphate
- Fatty amide
- N-acyl-amine
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Fatty acyl
- Tetraalkylammonium salt
- Carboxamide group
- Secondary carboxylic acid amide
- Secondary alcohol
- Carboxylic acid derivative
- Organopnictogen compound
- Organic oxygen compound
- Carbonyl group
- Organooxygen compound
- Amine
- Alcohol
- Organic oxide
- Organic salt
- Hydrocarbon derivative
- Organic cation
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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SM C16:1,2TMS,isomer #1 | CCCCCC/C=C/CCCCCCCC(=O)N[C@@H](COP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C)[C@@H](CCCCCCC/C=C/CCCCCCC)O[Si](C)(C)C | 4840.1 | Semi standard non polar | 33892256 | SM C16:1,2TMS,isomer #1 | CCCCCC/C=C/CCCCCCCC(=O)N[C@@H](COP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C)[C@@H](CCCCCCC/C=C/CCCCCCC)O[Si](C)(C)C | 4558.2 | Standard non polar | 33892256 | SM C16:1,2TMS,isomer #2 | CCCCCC/C=C/CCCCCCCC(=O)N([C@@H](COP(=O)(O)OCC[N+](C)(C)C)[C@@H](CCCCCCC/C=C/CCCCCCC)O[Si](C)(C)C)[Si](C)(C)C | 4831.2 | Semi standard non polar | 33892256 | SM C16:1,2TMS,isomer #2 | CCCCCC/C=C/CCCCCCCC(=O)N([C@@H](COP(=O)(O)OCC[N+](C)(C)C)[C@@H](CCCCCCC/C=C/CCCCCCC)O[Si](C)(C)C)[Si](C)(C)C | 4557.1 | Standard non polar | 33892256 | SM C16:1,2TMS,isomer #3 | CCCCCC/C=C/CCCCCCCC(=O)N([C@@H](COP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C)[C@H](O)CCCCCCC/C=C/CCCCCCC)[Si](C)(C)C | 4793.1 | Semi standard non polar | 33892256 | SM C16:1,2TMS,isomer #3 | CCCCCC/C=C/CCCCCCCC(=O)N([C@@H](COP(=O)(OCC[N+](C)(C)C)O[Si](C)(C)C)[C@H](O)CCCCCCC/C=C/CCCCCCC)[Si](C)(C)C | 4587.0 | Standard non polar | 33892256 |
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Spectra |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - SM C16:1 GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - SM C16:1 GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - SM C16:1 GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - SM C16:1 GC-MS (TBDMS_1_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - SM C16:1 GC-MS (TBDMS_1_2) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - SM C16:1 GC-MS (TBDMS_1_3) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - SM C16:1 10V, Positive-QTOF | splash10-01q1-6030394100-0921e5cc77015b10667a | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - SM C16:1 20V, Positive-QTOF | splash10-02a2-2170190000-45451da024085f9209cf | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - SM C16:1 40V, Positive-QTOF | splash10-001a-6090011000-8bf200d1cd2fcfe48fa4 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - SM C16:1 10V, Positive-QTOF | splash10-00ks-0500029300-2a5b5bb2c879a3980798 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - SM C16:1 20V, Positive-QTOF | splash10-000i-0900001000-d4e394196fc843390a1d | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - SM C16:1 40V, Positive-QTOF | splash10-0019-3900000000-244a63c757d071fe5688 | 2021-09-22 | Wishart Lab | View Spectrum |
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Biological Properties |
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Cellular Locations | - Membrane (predicted from logP)
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Detected and Quantified | 16.6 +/- 3.36 uM | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 0.1 +/- 0.12 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Feces | Detected and Quantified | 0.09 +/- 0.1 nmol/g wet feces | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 0.0009 (0.0004-0.0023) umol/mmol creatinine | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Blood | Detected and Quantified | 11.455 (10.081) uM | Adult (>18 years old) | Female | Pregnancy with fetus having congenital heart defect | | details | Blood | Detected and Quantified | 18.125 (15.986) uM | Adult (>18 years old) | Female | Pregnancy with fetus having congenital heart defect | | details | Blood | Detected and Quantified | 20.316 (4.306) uM | Adult (>18 years old) | Female | Pregnancy | | details | Blood | Detected and Quantified | 31.102 (6.468) uM | Adult (>18 years old) | Female | Pregnancy | | details |
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Associated Disorders and Diseases |
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Disease References | Pregnancy |
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- Bahado-Singh RO, Ertl R, Mandal R, Bjorndahl TC, Syngelaki A, Han B, Dong E, Liu PB, Alpay-Savasan Z, Wishart DS, Nicolaides KH: Metabolomic prediction of fetal congenital heart defect in the first trimester. Am J Obstet Gynecol. 2014 Sep;211(3):240.e1-240.e14. doi: 10.1016/j.ajog.2014.03.056. Epub 2014 Apr 1. [PubMed:24704061 ]
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB031404 |
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KNApSAcK ID | Not Available |
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Chemspider ID | Not Available |
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KEGG Compound ID | Not Available |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | Not Available |
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PubChem Compound | 124202091 |
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PDB ID | Not Available |
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ChEBI ID | 89104 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | MDB00029967 |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | Not Available |
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