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 21:47:35 UTC |
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Update Date | 2022-03-07 02:55:00 UTC |
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HMDB ID | HMDB0036630 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Trifolirhizin |
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Description | Trifolirhizin, also known as sophojaponicin B1, belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. Trifolirhizin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, trifolirhizin has been detected, but not quantified in, pulses. This could make trifolirhizin a potential biomarker for the consumption of these foods. |
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Structure | OCC1OC(OC2=CC=C3C4OC5=C(C=C6OCOC6=C5)C4COC3=C2)C(O)C(O)C1O InChI=1S/C22H22O10/c23-6-17-18(24)19(25)20(26)22(32-17)30-9-1-2-10-13(3-9)27-7-12-11-4-15-16(29-8-28-15)5-14(11)31-21(10)12/h1-5,12,17-26H,6-8H2 |
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Synonyms | Value | Source |
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(-)-Maackiain 3-O-glucoside | HMDB | Sophojaponicin b1 | HMDB |
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Chemical Formula | C22H22O10 |
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Average Molecular Weight | 446.4041 |
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Monoisotopic Molecular Weight | 446.121296924 |
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IUPAC Name | 2-(hydroxymethyl)-6-{5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2(10),3,8,13,15,17-hexaen-16-yloxy}oxane-3,4,5-triol |
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Traditional Name | 2-(hydroxymethyl)-6-{5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2(10),3,8,13,15,17-hexaen-16-yloxy}oxane-3,4,5-triol |
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CAS Registry Number | 6807-83-6 |
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SMILES | OCC1OC(OC2=CC=C3C4OC5=C(C=C6OCOC6=C5)C4COC3=C2)C(O)C(O)C1O |
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InChI Identifier | InChI=1S/C22H22O10/c23-6-17-18(24)19(25)20(26)22(32-17)30-9-1-2-10-13(3-9)27-7-12-11-4-15-16(29-8-28-15)5-14(11)31-21(10)12/h1-5,12,17-26H,6-8H2 |
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InChI Key | VGSYCWGXBYZLLE-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. |
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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 | Furanoisoflavonoids |
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Direct Parent | Pterocarpans |
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Alternative Parents | |
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Substituents | - Pterocarpan
- Isoflavanol
- Isoflavan
- Phenolic glycoside
- Glycosyl compound
- O-glycosyl compound
- Chromane
- Benzopyran
- 1-benzopyran
- Coumaran
- Benzodioxole
- Benzofuran
- Alkyl aryl ether
- Benzenoid
- Monosaccharide
- Oxane
- Secondary alcohol
- Polyol
- Ether
- Acetal
- Organoheterocyclic compound
- Oxacycle
- Primary alcohol
- Hydrocarbon derivative
- Alcohol
- Organic oxygen compound
- Organooxygen compound
- 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 | 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 | 142 - 144 °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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Trifolirhizin,1TMS,isomer #1 | C[Si](C)(C)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C(O)C1O | 3918.8 | Semi standard non polar | 33892256 | Trifolirhizin,1TMS,isomer #2 | C[Si](C)(C)OC1C(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)OC(CO)C(O)C1O | 3920.9 | Semi standard non polar | 33892256 | Trifolirhizin,1TMS,isomer #3 | C[Si](C)(C)OC1C(O)C(CO)OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C1O | 3921.2 | Semi standard non polar | 33892256 | Trifolirhizin,1TMS,isomer #4 | C[Si](C)(C)OC1C(CO)OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C1O | 3869.7 | Semi standard non polar | 33892256 | Trifolirhizin,2TMS,isomer #1 | C[Si](C)(C)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C)C(O)C1O | 3912.8 | Semi standard non polar | 33892256 | Trifolirhizin,2TMS,isomer #2 | C[Si](C)(C)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C(O[Si](C)(C)C)C1O | 3910.5 | Semi standard non polar | 33892256 | Trifolirhizin,2TMS,isomer #3 | C[Si](C)(C)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C(O)C1O[Si](C)(C)C | 3856.5 | Semi standard non polar | 33892256 | Trifolirhizin,2TMS,isomer #4 | C[Si](C)(C)OC1C(CO)OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C)C1O | 3890.6 | Semi standard non polar | 33892256 | Trifolirhizin,2TMS,isomer #5 | C[Si](C)(C)OC1C(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)OC(CO)C(O)C1O[Si](C)(C)C | 3908.0 | Semi standard non polar | 33892256 | Trifolirhizin,2TMS,isomer #6 | C[Si](C)(C)OC1C(CO)OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C1O[Si](C)(C)C | 3881.9 | Semi standard non polar | 33892256 | Trifolirhizin,3TMS,isomer #1 | C[Si](C)(C)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O | 3873.3 | Semi standard non polar | 33892256 | Trifolirhizin,3TMS,isomer #2 | C[Si](C)(C)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C | 3869.6 | Semi standard non polar | 33892256 | Trifolirhizin,3TMS,isomer #3 | C[Si](C)(C)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C | 3865.7 | Semi standard non polar | 33892256 | Trifolirhizin,3TMS,isomer #4 | C[Si](C)(C)OC1C(CO)OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C)C1O[Si](C)(C)C | 3863.4 | Semi standard non polar | 33892256 | Trifolirhizin,4TMS,isomer #1 | C[Si](C)(C)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C | 3840.8 | Semi standard non polar | 33892256 | Trifolirhizin,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C(O)C1O | 4139.2 | Semi standard non polar | 33892256 | Trifolirhizin,1TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OC1C(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)OC(CO)C(O)C1O | 4164.7 | Semi standard non polar | 33892256 | Trifolirhizin,1TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OC1C(O)C(CO)OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C1O | 4162.4 | Semi standard non polar | 33892256 | Trifolirhizin,1TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC1C(CO)OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C1O | 4108.4 | Semi standard non polar | 33892256 | Trifolirhizin,2TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C(C)(C)C)C(O)C1O | 4358.1 | Semi standard non polar | 33892256 | Trifolirhizin,2TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C(O[Si](C)(C)C(C)(C)C)C1O | 4364.7 | Semi standard non polar | 33892256 | Trifolirhizin,2TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C(O)C1O[Si](C)(C)C(C)(C)C | 4303.5 | Semi standard non polar | 33892256 | Trifolirhizin,2TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC1C(CO)OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C(C)(C)C)C1O | 4342.8 | Semi standard non polar | 33892256 | Trifolirhizin,2TBDMS,isomer #5 | CC(C)(C)[Si](C)(C)OC1C(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)OC(CO)C(O)C1O[Si](C)(C)C(C)(C)C | 4357.0 | Semi standard non polar | 33892256 | Trifolirhizin,2TBDMS,isomer #6 | CC(C)(C)[Si](C)(C)OC1C(CO)OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C1O[Si](C)(C)C(C)(C)C | 4340.6 | Semi standard non polar | 33892256 | Trifolirhizin,3TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O | 4496.1 | Semi standard non polar | 33892256 | Trifolirhizin,3TBDMS,isomer #2 | CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C | 4514.7 | Semi standard non polar | 33892256 | Trifolirhizin,3TBDMS,isomer #3 | CC(C)(C)[Si](C)(C)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C | 4487.1 | Semi standard non polar | 33892256 | Trifolirhizin,3TBDMS,isomer #4 | CC(C)(C)[Si](C)(C)OC1C(CO)OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C | 4467.1 | 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 - Trifolirhizin GC-MS (Non-derivatized) - 70eV, Positive | splash10-0fc9-6923500000-97b55526dbdcc8c8ca18 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Trifolirhizin GC-MS (3 TMS) - 70eV, Positive | splash10-0002-3584039000-ec07e3a2c359c1837894 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Trifolirhizin GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Trifolirhizin 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - Trifolirhizin LC-ESI-QTOF , negative-QTOF | splash10-001i-0090000000-ebff3ecfb3a07b7e899f | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Trifolirhizin LC-ESI-QTOF , negative-QTOF | splash10-001i-0090000000-c290e7b385d0d9ca6a41 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Trifolirhizin LC-ESI-QTOF , negative-QTOF | splash10-014i-0090000000-98db68821036b0540e17 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Trifolirhizin LC-ESI-QTOF , positive-QTOF | splash10-000i-0090000000-380363e70644b6306924 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Trifolirhizin LC-ESI-QTOF , positive-QTOF | splash10-000i-0090000000-b2849bbee2f75d81ec5b | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Trifolirhizin LC-ESI-QTOF , positive-QTOF | splash10-000i-0190000000-9bd5ec9680b1d26b729e | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Trifolirhizin 40V, Positive-QTOF | splash10-000i-0190000000-9bd5ec9680b1d26b729e | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trifolirhizin 10V, Positive-QTOF | splash10-000j-0190400000-ddf30adc6bb2bfa7791b | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trifolirhizin 20V, Positive-QTOF | splash10-000i-0190000000-e28d6bfe2ad48fb7566c | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trifolirhizin 40V, Positive-QTOF | splash10-052f-6970000000-aa34d28da05420666fc9 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trifolirhizin 10V, Positive-QTOF | splash10-000j-0190400000-ddf30adc6bb2bfa7791b | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trifolirhizin 20V, Positive-QTOF | splash10-000i-0190000000-e28d6bfe2ad48fb7566c | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trifolirhizin 40V, Positive-QTOF | splash10-052f-6970000000-aa34d28da05420666fc9 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trifolirhizin 10V, Positive-QTOF | splash10-000j-0190400000-ddf30adc6bb2bfa7791b | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trifolirhizin 20V, Positive-QTOF | splash10-000i-0190000000-e28d6bfe2ad48fb7566c | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trifolirhizin 40V, Positive-QTOF | splash10-052f-6970000000-aa34d28da05420666fc9 | 2015-04-24 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trifolirhizin 10V, Negative-QTOF | splash10-000t-1261900000-2769569424136309c848 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trifolirhizin 20V, Negative-QTOF | splash10-001i-1290200000-a8dffdbebb9530a8736c | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trifolirhizin 40V, Negative-QTOF | splash10-0f89-2190000000-a1038019731cf3d6d083 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trifolirhizin 10V, Negative-QTOF | splash10-000t-1261900000-2769569424136309c848 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trifolirhizin 20V, Negative-QTOF | splash10-001i-1290200000-a8dffdbebb9530a8736c | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trifolirhizin 40V, Negative-QTOF | splash10-0f89-2190000000-a1038019731cf3d6d083 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trifolirhizin 10V, Negative-QTOF | splash10-000t-1261900000-2769569424136309c848 | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trifolirhizin 20V, Negative-QTOF | splash10-001i-1290200000-a8dffdbebb9530a8736c | 2015-04-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Trifolirhizin 40V, Negative-QTOF | splash10-0f89-2190000000-a1038019731cf3d6d083 | 2015-04-25 | Wishart Lab | View Spectrum |
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