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 18:20:49 UTC |
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Update Date | 2022-03-07 02:53:47 UTC |
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HMDB ID | HMDB0033600 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Sagerinic acid |
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Description | Sagerinic acid, also known as sagerinate, belongs to the class of organic compounds known as cyclobutane lignans. These are lignans with a structure characterized by to phenylpropanoid units coupled together through the C7-C7' and C8-C8' bonds, forming a cyclobutane ring with the C7, C7', C8', and C8 atoms. Sagerinic acid has been detected, but not quantified in, several different foods, such as herbs and spices, green tea, teas (Camellia sinensis), black tea, and herbal tea. This could make sagerinic acid a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Sagerinic acid. |
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Structure | OC(=O)C(CC1=CC(O)=C(O)C=C1)OC(=O)C1C(C(C1C1=CC=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1)C(=O)OC(CC1=CC=C(O)C(O)=C1)C(O)=O InChI=1S/C36H32O16/c37-19-5-1-15(9-23(19)41)11-27(33(45)46)51-35(49)31-29(17-3-7-21(39)25(43)13-17)30(18-4-8-22(40)26(44)14-18)32(31)36(50)52-28(34(47)48)12-16-2-6-20(38)24(42)10-16/h1-10,13-14,27-32,37-44H,11-12H2,(H,45,46)(H,47,48) |
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Synonyms | Value | Source |
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Sagerinate | Generator | (+)-Sagerinic acid | HMDB | 2-(2-{[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-3,4-bis(3,4-dihydroxyphenyl)cyclobutanecarbonyloxy)-3-(3,4-dihydroxyphenyl)propanoate | Generator |
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Chemical Formula | C36H32O16 |
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Average Molecular Weight | 720.6297 |
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Monoisotopic Molecular Weight | 720.169034976 |
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IUPAC Name | 2-(2-{[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-3,4-bis(3,4-dihydroxyphenyl)cyclobutanecarbonyloxy)-3-(3,4-dihydroxyphenyl)propanoic acid |
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Traditional Name | 2-(2-{[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]carbonyl}-3,4-bis(3,4-dihydroxyphenyl)cyclobutanecarbonyloxy)-3-(3,4-dihydroxyphenyl)propanoic acid |
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CAS Registry Number | Not Available |
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SMILES | OC(=O)C(CC1=CC(O)=C(O)C=C1)OC(=O)C1C(C(C1C1=CC=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1)C(=O)OC(CC1=CC=C(O)C(O)=C1)C(O)=O |
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InChI Identifier | InChI=1S/C36H32O16/c37-19-5-1-15(9-23(19)41)11-27(33(45)46)51-35(49)31-29(17-3-7-21(39)25(43)13-17)30(18-4-8-22(40)26(44)14-18)32(31)36(50)52-28(34(47)48)12-16-2-6-20(38)24(42)10-16/h1-10,13-14,27-32,37-44H,11-12H2,(H,45,46)(H,47,48) |
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InChI Key | SUYLTDFWHNXGDX-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as cyclobutane lignans. These are lignans with a structure characterized by to phenylpropanoid units coupled together through the C7-C7' and C8-C8' bonds, forming a cyclobutane ring with the C7, C7', C8', and C8 atoms. |
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Kingdom | Organic compounds |
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Super Class | Lignans, neolignans and related compounds |
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Class | Cyclobutane lignans |
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Sub Class | Not Available |
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Direct Parent | Cyclobutane lignans |
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Alternative Parents | |
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Substituents | - Cyclobutane lignan skeleton
- Dibenzylbutane lignan skeleton
- Stilbene
- Tetracarboxylic acid or derivatives
- 3-phenylpropanoic-acid
- Catechol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Monocyclic benzene moiety
- Benzenoid
- Carboxylic acid ester
- Carboxylic acid derivative
- Carboxylic acid
- Organic oxygen compound
- Organic oxide
- Carbonyl group
- Hydrocarbon derivative
- Organooxygen compound
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic 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 | Not Available |
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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 Kovats Retention IndicesUnderivatized |
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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 - Sagerinic acid GC-MS (Non-derivatized) - 70eV, Positive | splash10-006t-1921520000-d96a4aca6c241e953a06 | 2017-11-06 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_1_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_1_2) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_1_3) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_1_4) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_1_5) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_1) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_2) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_3) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_4) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_5) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_6) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_7) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_8) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_9) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_10) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_11) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_12) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_13) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_14) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_15) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_16) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_17) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_18) - 70eV, Positive | Not Available | 2021-10-18 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Sagerinic acid GC-MS (TMS_2_19) - 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - Sagerinic acid , negative-QTOF | splash10-03di-0902000000-1a1faddf80089d58bfe8 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Sagerinic acid , positive-QTOF | splash10-03di-0900000000-bb8ee6e45c31480087a6 | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sagerinic acid 10V, Positive-QTOF | splash10-00di-0900041800-d8de10ee4e2aa08890f5 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sagerinic acid 20V, Positive-QTOF | splash10-00e9-0900122200-0106e5e32e7922dc081a | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sagerinic acid 40V, Positive-QTOF | splash10-00rb-0953101000-2db845aeb3f2c8245475 | 2016-06-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sagerinic acid 10V, Negative-QTOF | splash10-016r-0810261900-a79cd72c8538561fe873 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sagerinic acid 20V, Negative-QTOF | splash10-002r-0903452100-8b58476e06783bba06d8 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sagerinic acid 40V, Negative-QTOF | splash10-0a4i-0309410000-8447f34ee8e58a1b0e6c | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sagerinic acid 10V, Negative-QTOF | splash10-00os-0100938300-7f97188d37f68411f701 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sagerinic acid 20V, Negative-QTOF | splash10-00n1-0700689200-ebb7b001701a40c7bff6 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sagerinic acid 40V, Negative-QTOF | splash10-000e-0500839100-eb409f0d85ca4bfbf8b8 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sagerinic acid 10V, Positive-QTOF | splash10-0w90-0213546900-4a9855a0bb05002942c0 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sagerinic acid 20V, Positive-QTOF | splash10-000i-0319770000-2b0d4d4fdcfd32431da7 | 2021-09-25 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Sagerinic acid 40V, Positive-QTOF | splash10-0a4i-1902203000-7af6d10f702a823fe365 | 2021-09-25 | Wishart Lab | View Spectrum |
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