| Record Information |
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| Version | 2.0 |
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| Created at | 2022-03-17 20:43:03 UTC |
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| Updated at | 2022-03-17 20:43:03 UTC |
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| NP-MRD ID | NP0047613 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Silandrin |
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| Description | Silandrin belongs to the class of organic compounds known as flavonolignans. These are non-conventional lignans that derived from flavonoids. They are characterized by a p-dioxin ring substituted at one carbon atom by a C3C6 (phenylpropan) group and fused to the B-ring of the 2-phenylchromene moiety. Silandrin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Silandrin has been detected, but not quantified in, coffee and coffee products and green vegetables. Silandrin is found in Silybum marianum . This could make silandrin a potential biomarker for the consumption of these foods. |
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| Structure | COC1=C(O)C=CC(=C1)C1OC2=C(OC1CO)C=C(C=C2)C1CC(=O)C2=C(O1)C=C(O)C=C2O InChI=1S/C25H22O9/c1-31-20-7-13(2-4-15(20)28)25-23(11-26)33-21-6-12(3-5-18(21)34-25)19-10-17(30)24-16(29)8-14(27)9-22(24)32-19/h2-9,19,23,25-29H,10-11H2,1H3 |
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| Synonyms | Not Available |
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| Chemical Formula | C25H22O9 |
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| Average Mass | 466.4368 Da |
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| Monoisotopic Mass | 466.12638 Da |
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| IUPAC Name | 5,7-dihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-3,4-dihydro-2H-1-benzopyran-4-one |
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| Traditional Name | 5,7-dihydroxy-2-[2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydro-1-benzopyran-4-one |
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| CAS Registry Number | 70815-32-6 |
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| SMILES | COC1=C(O)C=CC(=C1)C1OC2=C(OC1CO)C=C(C=C2)C1CC(=O)C2=C(O1)C=C(O)C=C2O |
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| InChI Identifier | InChI=1S/C25H22O9/c1-31-20-7-13(2-4-15(20)28)25-23(11-26)33-21-6-12(3-5-18(21)34-25)19-10-17(30)24-16(29)8-14(27)9-22(24)32-19/h2-9,19,23,25-29H,10-11H2,1H3 |
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| InChI Key | CRPGUMMYQABYES-UHFFFAOYSA-N |
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| Experimental Spectra |
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| Not Available | | Predicted Spectra |
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| Not Available | | Chemical Shift Submissions |
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| Not Available | | Species |
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| Species of Origin | | Species Name | Source | Reference |
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| Coffea arabica L. | FooDB | - Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
| | Coffea canephora | FooDB | - Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
| | Silybum marianum | Plant | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as flavonolignans. These are non-conventional lignans that derived from flavonoids. They are characterized by a p-dioxin ring substituted at one carbon atom by a C3C6 (phenylpropan) group and fused to the B-ring of the 2-phenylchromene moiety. |
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| Kingdom | Organic compounds |
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| Super Class | Lignans, neolignans and related compounds |
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| Class | Flavonolignans |
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| Sub Class | Not Available |
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| Direct Parent | Flavonolignans |
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| Alternative Parents | |
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| Substituents | - Flavonolignan
- Hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Flavanone
- Flavan
- 2-phenylbenzo-1,4-dioxane
- Phenylbenzodioxane
- Chromone
- Methoxyphenol
- Benzo-1,4-dioxane
- Benzodioxane
- Chromane
- 1-benzopyran
- Benzopyran
- Phenoxy compound
- Anisole
- Methoxybenzene
- Phenol ether
- Aryl ketone
- Aryl alkyl ketone
- Alkyl aryl ether
- Phenol
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Monocyclic benzene moiety
- Benzenoid
- Para-dioxin
- Vinylogous acid
- Ketone
- Organoheterocyclic compound
- Oxacycle
- Ether
- Alcohol
- Primary alcohol
- Organic oxide
- 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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| Physical Properties |
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| State | Not Available |
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| Experimental 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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| Predicted Properties | |
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