| Record Information |
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| Version | 2.0 |
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| Created at | 2022-03-17 21:02:38 UTC |
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| Updated at | 2022-03-17 21:02:39 UTC |
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| NP-MRD ID | NP0048817 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | Trilobatin |
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| Description | Trilobatin, also known as p-phloridzin, belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. Thus, trilobatin is considered to be a flavonoid lipid molecule. Trilobatin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, Trilobatin has been detected, but not quantified in, pomes. Trilobatin is found in Balanophora harlandii, Balanophora tobiracola, Lithocarpus liseifolius, Lithocarpus litseifolius, Lithocarpus pachyphyllus, Lithocarpus polystachya, Lithocarpus polystachyus, Malus trilobata, Symplocos microcalyx, Vitis piasezkii, Vitis saccharifera and Vitis vinifera. This could make trilobatin a potential biomarker for the consumption of these foods. |
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| Structure | OCC1OC(OC2=CC(O)=C(C(=O)CCC3=CC=C(O)C=C3)C(O)=C2)C(O)C(O)C1O InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-12-7-14(25)17(15(26)8-12)13(24)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-23,25-29H,3,6,9H2 |
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| Synonyms | | Value | Source |
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| p-Phloridzin | HMDB | | p-Phlorizin | HMDB | | Phloretin-4'-O-glucoside | MeSH |
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| Chemical Formula | C21H24O10 |
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| Average Mass | 436.4093 Da |
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| Monoisotopic Mass | 436.13695 Da |
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| IUPAC Name | 1-(2,6-dihydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)propan-1-one |
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| Traditional Name | trilobatin |
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| CAS Registry Number | 4192-90-9 |
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| SMILES | OCC1OC(OC2=CC(O)=C(C(=O)CCC3=CC=C(O)C=C3)C(O)=C2)C(O)C(O)C1O |
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| InChI Identifier | InChI=1S/C21H24O10/c22-9-16-18(27)19(28)20(29)21(31-16)30-12-7-14(25)17(15(26)8-12)13(24)6-3-10-1-4-11(23)5-2-10/h1-2,4-5,7-8,16,18-23,25-29H,3,6,9H2 |
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| InChI Key | GSTCPEBQYSOEHV-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 | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as flavonoid o-glycosides. Flavonoid O-glycosides are compounds containing a carbohydrate moiety which is O-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. |
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| Kingdom | Organic compounds |
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| Super Class | Phenylpropanoids and polyketides |
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| Class | Flavonoids |
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| Sub Class | Flavonoid glycosides |
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| Direct Parent | Flavonoid O-glycosides |
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| Alternative Parents | |
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| Substituents | - Flavonoid o-glycoside
- 2'-hydroxy-dihydrochalcone
- Linear 1,3-diarylpropanoid
- Cinnamylphenol
- Phenolic glycoside
- Alkyl-phenylketone
- Hexose monosaccharide
- O-glycosyl compound
- Glycosyl compound
- Butyrophenone
- Phenylketone
- Aryl alkyl ketone
- Aryl ketone
- Benzoyl
- Resorcinol
- Phenoxy compound
- Phenol ether
- 1-hydroxy-2-unsubstituted benzenoid
- 1-hydroxy-4-unsubstituted benzenoid
- Phenol
- Benzenoid
- Monocyclic benzene moiety
- Monosaccharide
- Oxane
- Vinylogous acid
- Secondary alcohol
- Ketone
- Acetal
- Organoheterocyclic compound
- Oxacycle
- Polyol
- Primary alcohol
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Organic oxygen compound
- Organooxygen compound
- Aromatic heteromonocyclic compound
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| Molecular Framework | Aromatic heteromonocyclic compounds |
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| External Descriptors | |
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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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