Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-11 18:39:18 UTC |
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Update Date | 2022-03-07 02:53:53 UTC |
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HMDB ID | HMDB0033882 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Glycyrol |
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Description | Glycyrol, also known as neoglycyrol, belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. Glycyrol is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, glycyrol has been detected, but not quantified in, root vegetables. This could make glycyrol a potential biomarker for the consumption of these foods. |
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Structure | COC1=C(CC=C(C)C)C(O)=CC2=C1C1=C(C3=C(O1)C=C(O)C=C3)C(=O)O2 InChI=1S/C21H18O6/c1-10(2)4-6-12-14(23)9-16-18(19(12)25-3)20-17(21(24)27-16)13-7-5-11(22)8-15(13)26-20/h4-5,7-9,22-23H,6H2,1-3H3 |
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Synonyms | Value | Source |
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1,9-Dihydroxy-3-methoxy-2-prenylcoumestan | ChEBI | Neoglycyrol | ChEBI | 3,9-Dihydroxy-1-methoxy-2-prenylcoumestan | HMDB |
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Chemical Formula | C21H18O6 |
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Average Molecular Weight | 366.364 |
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Monoisotopic Molecular Weight | 366.110338308 |
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IUPAC Name | 5,14-dihydroxy-3-methoxy-4-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one |
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Traditional Name | 5,14-dihydroxy-3-methoxy-4-(3-methylbut-2-en-1-yl)-8,17-dioxatetracyclo[8.7.0.0²,⁷.0¹¹,¹⁶]heptadeca-1(10),2(7),3,5,11(16),12,14-heptaen-9-one |
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CAS Registry Number | 23013-84-5 |
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SMILES | COC1=C(CC=C(C)C)C(O)=CC2=C1C1=C(C3=C(O1)C=C(O)C=C3)C(=O)O2 |
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InChI Identifier | InChI=1S/C21H18O6/c1-10(2)4-6-12-14(23)9-16-18(19(12)25-3)20-17(21(24)27-16)13-7-5-11(22)8-15(13)26-20/h4-5,7-9,22-23H,6H2,1-3H3 |
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InChI Key | LWESBHWAOZORCQ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as coumestans. These are polycyclic aromatic compounds containing a coumestan moiety, which consists of a benzoxole fused to a chromen-2-one to form 1-Benzoxolo[3,2-c]chromen-6-one. They are oxidation products of pterocarpan. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Isoflavonoids |
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Sub Class | Coumestans |
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Direct Parent | Coumestans |
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Alternative Parents | |
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Substituents | - Coumestan
- Angular furanocoumarin
- Furanocoumarin
- Coumarin
- Benzopyran
- 1-benzopyran
- Benzofuran
- Furopyran
- Anisole
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Pyranone
- Benzenoid
- Pyran
- Heteroaromatic compound
- Furan
- Lactone
- Organoheterocyclic compound
- Oxacycle
- Ether
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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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 | 243.5 - 245 °C | 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 Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Glycyrol,1TMS,isomer #1 | COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=CC2=C1C1=C(C(=O)O2)C2=CC=C(O)C=C2O1 | 3472.6 | Semi standard non polar | 33892256 | Glycyrol,1TMS,isomer #2 | COC1=C(CC=C(C)C)C(O)=CC2=C1C1=C(C(=O)O2)C2=CC=C(O[Si](C)(C)C)C=C2O1 | 3501.4 | Semi standard non polar | 33892256 | Glycyrol,2TMS,isomer #1 | COC1=C(CC=C(C)C)C(O[Si](C)(C)C)=CC2=C1C1=C(C(=O)O2)C2=CC=C(O[Si](C)(C)C)C=C2O1 | 3529.1 | Semi standard non polar | 33892256 | Glycyrol,1TBDMS,isomer #1 | COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C1=C(C(=O)O2)C2=CC=C(O)C=C2O1 | 3670.9 | Semi standard non polar | 33892256 | Glycyrol,1TBDMS,isomer #2 | COC1=C(CC=C(C)C)C(O)=CC2=C1C1=C(C(=O)O2)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O1 | 3701.7 | Semi standard non polar | 33892256 | Glycyrol,2TBDMS,isomer #1 | COC1=C(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC2=C1C1=C(C(=O)O2)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C2O1 | 3971.2 | Semi standard non polar | 33892256 |
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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 - Glycyrol GC-MS (Non-derivatized) - 70eV, Positive | splash10-0f79-1129000000-4b993b33166cb8fbdde8 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Glycyrol GC-MS (2 TMS) - 70eV, Positive | splash10-002k-2040900000-e8542ceec5c4a158aaee | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Glycyrol GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Glycyrol 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 |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycyrol 10V, Positive-QTOF | splash10-014i-0009000000-78e48e684af3992efae3 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycyrol 20V, Positive-QTOF | splash10-02t9-2009000000-559fde7e518d612551bc | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycyrol 40V, Positive-QTOF | splash10-02t9-9353000000-cbb9dd6f93c1a2e64277 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycyrol 10V, Negative-QTOF | splash10-014i-0009000000-a33d47de2f3004d70f99 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycyrol 20V, Negative-QTOF | splash10-014i-0019000000-c6efce8ed6331ff56fea | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycyrol 40V, Negative-QTOF | splash10-067i-1965000000-11a2427325da7ae4a8f8 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycyrol 10V, Positive-QTOF | splash10-014i-0009000000-265ec74b35410de9b3c6 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycyrol 20V, Positive-QTOF | splash10-03di-0009000000-8f50112b7b5413a648fb | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycyrol 40V, Positive-QTOF | splash10-00lg-0096000000-4a4f3bb3782eaa146d29 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycyrol 10V, Negative-QTOF | splash10-014i-0009000000-72365573e5c49658d9fe | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycyrol 20V, Negative-QTOF | splash10-014i-0019000000-bbb249d50e49f95b73d9 | 2021-09-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Glycyrol 40V, Negative-QTOF | splash10-03di-1149000000-5c8c3be792050956e0d1 | 2021-09-24 | Wishart Lab | View Spectrum |
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General References | - Shin EM, Zhou HY, Guo LY, Kim JA, Lee SH, Merfort I, Kang SS, Kim HS, Kim S, Kim YS: Anti-inflammatory effects of glycyrol isolated from Glycyrrhiza uralensis in LPS-stimulated RAW264.7 macrophages. Int Immunopharmacol. 2008 Nov;8(11):1524-32. doi: 10.1016/j.intimp.2008.06.008. Epub 2008 Jul 11. [PubMed:18621150 ]
- (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
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