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 23:23:13 UTC |
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Update Date | 2022-03-07 02:55:37 UTC |
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HMDB ID | HMDB0038102 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | (R)-Hispaglabridin A |
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Description | (R)-Hispaglabridin A belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton (R)-Hispaglabridin A has been detected, but not quantified in, several different foods, such as green tea, herbal tea, black tea, herbs and spices, and red tea. This could make (R)-hispaglabridin a a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (R)-Hispaglabridin A. |
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Structure | CC(C)=CCC1=C(O)C=CC(C2COC3=C(C2)C=CC2=C3C=CC(C)(C)O2)=C1O InChI=1S/C25H28O4/c1-15(2)5-7-19-21(26)9-8-18(23(19)27)17-13-16-6-10-22-20(24(16)28-14-17)11-12-25(3,4)29-22/h5-6,8-12,17,26-27H,7,13-14H2,1-4H3 |
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Synonyms | Value | Source |
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Hispaglabridin a | HMDB |
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Chemical Formula | C25H28O4 |
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Average Molecular Weight | 392.4874 |
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Monoisotopic Molecular Weight | 392.198759384 |
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IUPAC Name | 4-{12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8,13-tetraen-5-yl}-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol |
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Traditional Name | 4-{12,12-dimethyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1(10),2(7),8,13-tetraen-5-yl}-2-(3-methylbut-2-en-1-yl)benzene-1,3-diol |
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CAS Registry Number | 68978-03-0 |
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SMILES | CC(C)=CCC1=C(O)C=CC(C2COC3=C(C2)C=CC2=C3C=CC(C)(C)O2)=C1O |
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InChI Identifier | InChI=1S/C25H28O4/c1-15(2)5-7-19-21(26)9-8-18(23(19)27)17-13-16-6-10-22-20(24(16)28-14-17)11-12-25(3,4)29-22/h5-6,8-12,17,26-27H,7,13-14H2,1-4H3 |
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InChI Key | HZHXMXSXYQCAIG-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as pyranoisoflavonoids. These are isoflavonoids that contain a pyran ring fused to either of the A, B, or C ring of the isoflavonoid skeleton. |
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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 | Pyranoisoflavonoids |
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Direct Parent | Pyranoisoflavonoids |
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Alternative Parents | |
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Substituents | - Pyranoisoflavonoid
- Hydroxyisoflavonoid
- Isoflavanol
- Isoflavan
- Pyranochromene
- 2,2-dimethyl-1-benzopyran
- Chromane
- Benzopyran
- 1-benzopyran
- Resorcinol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Alkyl aryl ether
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Oxacycle
- Organoheterocyclic compound
- Ether
- Organic oxygen compound
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic 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 | 132 - 133 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.0035 mg/L @ 25 °C (est) | The Good Scents Company Information System | 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. | 8.82 minutes | 32390414 | Predicted by Siyang on May 30, 2022 | 17.0164 minutes | 33406817 | Predicted by Siyang using ReTip algorithm on June 8, 2022 | 1.21 minutes | 32390414 | AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid | 28.4 seconds | 40023050 | Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid | 3028.3 seconds | 40023050 | Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid | 330.3 seconds | 40023050 | Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid | 229.8 seconds | 40023050 | Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid | 173.3 seconds | 40023050 | RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 168.0 seconds | 40023050 | Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid | 866.6 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 | 766.2 seconds | 40023050 | HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate) | 86.8 seconds | 40023050 | UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid | 1623.7 seconds | 40023050 | BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid | 685.2 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 | 1328.3 seconds | 40023050 | SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 573.3 seconds | 40023050 | RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid | 473.9 seconds | 40023050 | MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate | 268.4 seconds | 40023050 | KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA | 290.6 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 | 8.5 seconds | 40023050 |
Predicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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(R)-Hispaglabridin A,1TMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C)C=CC(C2COC3=C(C=CC4=C3C=CC(C)(C)O4)C2)=C1O | 3181.2 | Semi standard non polar | 33892256 | (R)-Hispaglabridin A,1TMS,isomer #2 | CC(C)=CCC1=C(O)C=CC(C2COC3=C(C=CC4=C3C=CC(C)(C)O4)C2)=C1O[Si](C)(C)C | 3155.6 | Semi standard non polar | 33892256 | (R)-Hispaglabridin A,2TMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C)C=CC(C2COC3=C(C=CC4=C3C=CC(C)(C)O4)C2)=C1O[Si](C)(C)C | 3102.5 | Semi standard non polar | 33892256 | (R)-Hispaglabridin A,1TBDMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC(C2COC3=C(C=CC4=C3C=CC(C)(C)O4)C2)=C1O | 3426.5 | Semi standard non polar | 33892256 | (R)-Hispaglabridin A,1TBDMS,isomer #2 | CC(C)=CCC1=C(O)C=CC(C2COC3=C(C=CC4=C3C=CC(C)(C)O4)C2)=C1O[Si](C)(C)C(C)(C)C | 3395.8 | Semi standard non polar | 33892256 | (R)-Hispaglabridin A,2TBDMS,isomer #1 | CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C=CC(C2COC3=C(C=CC4=C3C=CC(C)(C)O4)C2)=C1O[Si](C)(C)C(C)(C)C | 3522.4 | 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 - (R)-Hispaglabridin A GC-MS (Non-derivatized) - 70eV, Positive | splash10-004i-2219000000-a4e3325ed2f7f79ad8fa | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (R)-Hispaglabridin A GC-MS (2 TMS) - 70eV, Positive | splash10-00di-3005590000-0b5230e41e8ae2ab2a75 | 2017-10-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - (R)-Hispaglabridin A 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 - (R)-Hispaglabridin A 10V, Positive-QTOF | splash10-000l-1709000000-0ed3e15b4b24770f7776 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 20V, Positive-QTOF | splash10-000i-2938000000-6676cb29bd9423cc9e18 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 40V, Positive-QTOF | splash10-00ks-3920000000-04df62888c77ab7fa9a4 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 10V, Negative-QTOF | splash10-0006-0219000000-087de2f429549d436dbb | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 20V, Negative-QTOF | splash10-00p3-0958000000-593fa8e9856ddf15519a | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 40V, Negative-QTOF | splash10-0kl9-0922000000-72064c560c7b5d72e564 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 10V, Positive-QTOF | splash10-000i-0029000000-1a83a6b9dedc8868beaa | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 20V, Positive-QTOF | splash10-000i-0219000000-c9561e8f3fea2f732c5a | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 40V, Positive-QTOF | splash10-0550-2987000000-13f9084eeec9d0f1abb8 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 10V, Negative-QTOF | splash10-0006-0009000000-fc8307e58aa68e585da3 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 20V, Negative-QTOF | splash10-0006-0009000000-0c85109cd9f3a11f33c0 | 2021-09-22 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - (R)-Hispaglabridin A 40V, Negative-QTOF | splash10-052r-1915000000-1b6b30c7b8401382cf93 | 2021-09-22 | Wishart Lab | View Spectrum |
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