| Record Information |
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| Version | 2.0 |
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| Created at | 2025-06-26 20:18:37 UTC |
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| Updated at | 2025-06-29 06:32:50 UTC |
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| NP-MRD ID | NP0351167 |
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| Natural Product DOI | https://doi.org/10.57994/4157 |
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| Secondary Accession Numbers | None |
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| Natural Product Identification |
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| Common Name | kaempferol-3-O-α-rhamnoside |
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| Description | Afzelin, also known as kaempferin or deacyl-SL0101, belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Afzelin is an extremely weak basic (essentially neutral) compound (based on its pKa). kaempferol-3-O-α-rhamnoside was first documented in 2013 (PMID: 23626759). A glycosyloxyflavone that is kaempferol attached to a alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage (PMID: 24423008) (PMID: 24642906) (PMID: 40482233). |
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| Structure | C[C@@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O InChI=1S/C21H20O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-18,21-25,27-28H,1H3/t8-,15-,17+,18+,21-/m0/s1 |
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| Synonyms | | Value | Source |
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| Kaempferin | ChEBI | | Kaempferol 3-O-alpha-L-rhamnoside | ChEBI | | Kaempferol 3-O-a-L-rhamnoside | Generator | | Kaempferol 3-O-α-L-rhamnoside | Generator | | Kaempferol-3-rhamnoside | MeSH | | Kaempferol-3-O-alpha-L-rhamnoside | MeSH | | Deacyl-SL0101 | MeSH | | 3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one | PhytoBank | | 3-[(6-Deoxy-α-L-mannopyranosyl)oxy]-5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one | PhytoBank | | 3-O-alpha-L-Rhamnopyranosylkaempferol | PhytoBank | | 3-O-α-L-Rhamnopyranosylkaempferol | PhytoBank | | Afzeloside | PhytoBank | | Kaempferol 3-(6-deoxy-L-mannopyranoside) | PhytoBank | | Kaempferol 3-L-rhamnoside | PhytoBank | | Kaempferol 3-O-rhamnopyranoside | PhytoBank | | Kaempferol 3-O-rhamnoside | PhytoBank | | Kaempferol 3-O-alpha-L-rhamnopyranoside | PhytoBank | | Kaempferol 3-O-α-L-rhamnopyranoside | PhytoBank | | Kaempferol 3-rhamnoside | PhytoBank | | Kaempferol 3-alpha-L-rhamnopyranoside | PhytoBank | | Kaempferol 3-α-L-rhamnopyranoside | PhytoBank | | Kaempferol rhamnoside | PhytoBank | | Kaempferol-3-alpha-L-rhamnose | PhytoBank | | Kaempferol-3-α-L-rhamnose | PhytoBank | | Kaempherol 3-O-alpha-L-rhamnopyranoside | PhytoBank | | Kaempherol 3-O-α-L-rhamnopyranoside | PhytoBank | | Kaempherol 3-O-alpha-rhamnoside | PhytoBank | | Kaempherol 3-O-α-rhamnoside | PhytoBank |
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| Chemical Formula | C21H20O10 |
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| Average Mass | 432.3775 Da |
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| Monoisotopic Mass | 432.10565 Da |
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| IUPAC Name | 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one |
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| Traditional Name | 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one |
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| CAS Registry Number | Not Available |
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| SMILES | C[C@@H]1O[C@@H](OC2=C(OC3=CC(O)=CC(O)=C3C2=O)C2=CC=C(O)C=C2)[C@H](O)[C@H](O)[C@H]1O |
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| InChI Identifier | InChI=1S/C21H20O10/c1-8-15(25)17(27)18(28)21(29-8)31-20-16(26)14-12(24)6-11(23)7-13(14)30-19(20)9-2-4-10(22)5-3-9/h2-8,15,17-18,21-25,27-28H,1H3/t8-,15-,17+,18+,21-/m0/s1 |
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| InChI Key | SOSLMHZOJATCCP-AEIZVZFYSA-N |
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| Experimental Spectra |
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| | Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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| HMBC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | ististiqamah@gmail.com | Institut Teknologi Bandung | Isti Istiqamah | 2025-06-26 | View Spectrum | | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | ististiqamah@gmail.com | Institut Teknologi Bandung | Isti Istiqamah | 2025-06-26 | View Spectrum | | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CD3OD, experimental) | ististiqamah@gmail.com | Institut Teknologi Bandung | Isti Istiqamah | 2025-06-26 | View Spectrum | | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, CD3OD, experimental) | ististiqamah@gmail.com | Institut Teknologi Bandung | Isti Istiqamah | 2025-06-26 | View Spectrum |
| | 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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| Pometia pinnata | | |
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| Chemical Taxonomy |
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| Description | Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. |
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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-3-O-glycosides |
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| Alternative Parents | |
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| Substituents | - Flavonoid-3-o-glycoside
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Flavone
- Hydroxyflavonoid
- Hexose monosaccharide
- Chromone
- Glycosyl compound
- O-glycosyl compound
- Benzopyran
- 1-benzopyran
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Pyranone
- Pyran
- Oxane
- Monocyclic benzene moiety
- Benzenoid
- Monosaccharide
- Heteroaromatic compound
- Vinylogous acid
- Secondary alcohol
- Oxacycle
- Polyol
- Acetal
- Organoheterocyclic compound
- Hydrocarbon derivative
- Organic oxide
- Organooxygen compound
- Alcohol
- Organic oxygen compound
- Aromatic heteropolycyclic compound
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| Molecular Framework | Aromatic heteropolycyclic 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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| General References | - Shin SW, Jung E, Kim S, Kim JH, Kim EG, Lee J, Park D: Antagonizing effects and mechanisms of afzelin against UVB-induced cell damage. PLoS One. 2013 Apr 23;8(4):e61971. doi: 10.1371/journal.pone.0061971. Print 2013. [PubMed:23626759 ]
- Jiang Y, Lu Y, Zhang YY, Chen DF: Anti-complementary constituents of Houttuynia cordata and their targets in complement activation cascade. Nat Prod Res. 2014;28(6):407-10. doi: 10.1080/14786419.2013.869693. Epub 2014 Jan 15. [PubMed:24423008 ]
- Lee SY, So YJ, Shin MS, Cho JY, Lee J: Antibacterial effects of afzelin isolated from Cornus macrophylla on Pseudomonas aeruginosa, a leading cause of illness in immunocompromised individuals. Molecules. 2014 Mar 17;19(3):3173-80. doi: 10.3390/molecules19033173. [PubMed:24642906 ]
- Istiqamah I, Herliana H, Fadilah A, Diniresna A, Fitriani R, Insanu M, Hermawati E, Happyana N: Secondary metabolites from Pometia pinnata leaves. Nat Prod Res. 2025 Jun 7:1-6. doi: 10.1080/14786419.2025.2514736. [PubMed:40482233 ]
- DOI: 10.1080/14786419.2025.2514736
- PMID: 40482233
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