Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2009-01-08 17:24:04 UTC |
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Update Date | 2022-11-30 19:04:00 UTC |
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HMDB ID | HMDB0011532 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | MG(0:0/15:0/0:0) |
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Description | MG(0:0/15:0/0:0) is a monoacylglyceride. A monoglyceride, more correctly known as a monoacylglycerol, is a glyceride consisting of one fatty acid chain covalently bonded to a glycerol molecule through an ester linkage. Monoacylglycerol can be broadly divided into two groups; 1-monoacylglycerols (or 3-monoacylglycerols) and 2-monoacylglycerols, depending on the position of the ester bond on the glycerol moiety. Normally the 1-/3-isomers are not distinguished from each other and are termed 'alpha-monoacylglycerols', while the 2-isomers are beta-monoacylglycerols. Monoacylglycerols are formed biochemically via release of a fatty acid from diacylglycerol by diacylglycerol lipase or hormone sensitive lipase. Monoacylglycerols are broken down by monoacylglycerol lipase. They tend to be minor components only of most plant and animal tissues, and indeed would not be expected to accumulate because their strong detergent properties would have a disruptive effect on membranes. 2-Monoacylglycerols are a major end product of the intestinal digestion of dietary fats in animals via the enzyme pancreatic lipase. They are taken up directly by the intestinal cells and converted to triacylglycerols via the monoacylglycerol pathway before being transported in lymph to the liver. Mono- and Diglycerides are commonly added to commercial food products in small quantities. They act as emulsifiers, helping to mix ingredients such as oil and water that would not otherwise blend well. |
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Structure | [H]C(CO)(CO)OC(=O)CCCCCCCCCCCCCC InChI=1S/C18H36O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-18(21)22-17(15-19)16-20/h17,19-20H,2-16H2,1H3 |
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Synonyms | Value | Source |
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1-Monoacylglyceride | HMDB | 1-Monoacylglycerol | HMDB | 2-Pentadecanoyl-glycerol | HMDB | 2-Pentadecanoyl-rac-glycerol | HMDB | b-Monoacylglycerol | HMDB | beta-Monoacylglycerol | HMDB | MAG(0:0/15:0) | HMDB | MAG(15:0) | HMDB | MG(0:0/15:0) | HMDB | MG(15:0) | HMDB | 1,3-Dihydroxypropan-2-yl pentadecanoic acid | HMDB |
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Chemical Formula | C18H36O4 |
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Average Molecular Weight | 316.476 |
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Monoisotopic Molecular Weight | 316.26135964 |
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IUPAC Name | 1,3-dihydroxypropan-2-yl pentadecanoate |
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Traditional Name | 1,3-dihydroxypropan-2-yl pentadecanoate |
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CAS Registry Number | Not Available |
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SMILES | [H]C(CO)(CO)OC(=O)CCCCCCCCCCCCCC |
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InChI Identifier | InChI=1S/C18H36O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-18(21)22-17(15-19)16-20/h17,19-20H,2-16H2,1H3 |
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InChI Key | SJUYTIGRIZBTCI-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as 2-monoacylglycerols. These are monoacylglycerols containing a glycerol acylated at the 2-position. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Glycerolipids |
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Sub Class | Monoradylglycerols |
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Direct Parent | 2-monoacylglycerols |
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Alternative Parents | |
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Substituents | - 2-acyl-sn-glycerol
- Fatty acid ester
- Fatty acyl
- Carboxylic acid ester
- Monocarboxylic acid or derivatives
- Carboxylic acid derivative
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Alcohol
- 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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Not Available | Not Available |
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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 | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Retention Times UnderivatizedChromatographic Method | Retention Time | Reference |
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Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022. | 10.0 minutes | 32390414 | Predicted by Siyang on May 30, 2022 | 18.2307 minutes | 33406817 | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 1.35 minutes | 32390414 | AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid | 37.3 seconds | 40023050 | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 3097.5 seconds | 40023050 | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 375.6 seconds | 40023050 | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 204.3 seconds | 40023050 | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 192.7 seconds | 40023050 | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 559.2 seconds | 40023050 | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 784.7 seconds | 40023050 | BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid | 775.4 seconds | 40023050 | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 119.8 seconds | 40023050 | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 1695.1 seconds | 40023050 | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 584.1 seconds | 40023050 | UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid | 1789.9 seconds | 40023050 | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 606.3 seconds | 40023050 | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 461.9 seconds | 40023050 | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 527.2 seconds | 40023050 | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 383.5 seconds | 40023050 | Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water | 14.7 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatizedDerivatized |
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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 ]
- Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. [PubMed:9034165 ]
- Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
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