Record Information |
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Version | 2.0 |
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Created at | 2007-01-22 22:44:31 UTC |
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Updated at | 2024-09-03 04:15:46 UTC |
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NP-MRD ID | NP0000460 |
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Natural Product DOI | https://doi.org/10.57994/0396 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Kaempferol |
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Description | Kaempferol, also known as rhamnolutein or c.I. 75640, Belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, kaempferol is considered to be a flavonoid molecule. A tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 5, 7 and 4'. Kaempferol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Kaempferol exists in all eukaryotes, ranging from yeast to humans. Kaempferol is a bitter tasting compound. Kaempferol is found, on average, in the highest concentration within a few different foods, such as saffrons, capers, and cumins and in a lower concentration in lovages, endives, and cloves. Kaempferol has also been detected, but not quantified, in several different foods, such as shallots, pine nuts, feijoa, kombus, and chicory leaves. This could make kaempferol a potential biomarker for the consumption of these foods. Kaempferol is a potentially toxic compound. |
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Structure | OC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 InChI=1S/C15H10O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,16-18,20H |
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Synonyms | Value | Source |
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3,4',5,7-Tetrahydroxyflavone | ChEBI | 4H-1-Benzopyran-4-one, 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-5,7,4'-trihydroxyflavonol | ChEBI | 5,7,4'-Trihydroxyflavonol | ChEBI | C.I. 75640 | ChEBI | Campherol | ChEBI | Indigo yellow | ChEBI | Kaempherol | ChEBI | Kampherol | ChEBI | Kempferol | ChEBI | Nimbecetin | ChEBI | Pelargidenolon | ChEBI | Populnetin | ChEBI | Rhamnolutein | ChEBI | Rhamnolutin | ChEBI | Robigenin | ChEBI | Swartziol | ChEBI | Trifolitin | ChEBI | 3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one | Kegg | 3,4',5,7-Tetrahydroxy-flavone (7ci,8ci) | HMDB | 3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one | HMDB | Kampferol | HMDB | 3,4’,5,7-tetrahydroxyflavone | HMDB | 3,5,7,4'-Tetrahydroxyflavone | HMDB | 3,5,7,4’-tetrahydroxyflavone | HMDB | 3'-Deoxyquercetin | HMDB | 3’-deoxyquercetin | HMDB | 5,7,4’-trihydroxyflavonol | HMDB | Kaemferol | HMDB | Kampcetin | HMDB | Pelargidenon | HMDB | Kaempferol | PhytoBank |
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Chemical Formula | C15H10O6 |
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Average Mass | 286.2363 Da |
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Monoisotopic Mass | 286.04774 Da |
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IUPAC Name | 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one |
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Traditional Name | kaempferol |
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CAS Registry Number | 520-18-3 |
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SMILES | OC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O1)C=C(O)C=C2O |
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InChI Identifier | InChI=1S/C15H10O6/c16-8-3-1-7(2-4-8)15-14(20)13(19)12-10(18)5-9(17)6-11(12)21-15/h1-6,16-18,20H |
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InChI Key | IYRMWMYZSQPJKC-UHFFFAOYSA-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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1D NMR | 1H NMR Spectrum (1D, 700 MHz, H2O, simulated) | Ahselim | | | 2022-01-06 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol, simulated) | Varshavi.d26 | | | 2021-09-06 | View Spectrum | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2023-12-21 | View Spectrum | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2023-12-21 | View Spectrum | COSY NMR | [1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2023-12-21 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2023-12-21 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, CD3OD, experimental) | bgnzk@missouri.edu | MU Metabolomics Center, University of Missouri, Columbia. MO, USA | Dr. Bharat Goel | 2023-12-21 | View Spectrum | ROESY NMR | [1H, 1H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | lpecio@iung.pulawy.pl | Not Available | Not Available | 2023-01-14 | View Spectrum | HSQC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | lpecio@iung.pulawy.pl | Not Available | Not Available | 2023-01-14 | View Spectrum | HMBC NMR | [1H, 13C] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | lpecio@iung.pulawy.pl | Not Available | Not Available | 2023-01-14 | View Spectrum | COSY NMR | [1H, 1H] NMR Spectrum (2D, 500 MHz, CD3OD, experimental) | lpecio@iung.pulawy.pl | Not Available | Not Available | 2023-01-14 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, CD3OD, experimental) | lpecio@iung.pulawy.pl | Not Available | Not Available | 2023-01-14 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, CD3OD, experimental) | lpecio@iung.pulawy.pl | Not Available | Not Available | 2023-01-14 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 125 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 150 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 175 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 225 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 25 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 250 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, Methanol-d4, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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| Chemical Shift Submissions |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 500.2, CD3OD, simulated) | lpecio@iung.pulawy.pl | Not Available | Not Available | 2024-05-11 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, Methanol, simulated) | varshavi.d26@gmail.com | Not Available | Not Available | 2021-08-16 | View Spectrum |
| 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 flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-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 | Flavones |
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Direct Parent | Flavonols |
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Alternative Parents | |
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Substituents | - 3-hydroxyflavone
- 3-hydroxyflavonoid
- 4'-hydroxyflavonoid
- 5-hydroxyflavonoid
- 7-hydroxyflavonoid
- Hydroxyflavonoid
- Chromone
- Benzopyran
- 1-benzopyran
- 1-hydroxy-4-unsubstituted benzenoid
- 1-hydroxy-2-unsubstituted benzenoid
- Phenol
- Pyranone
- Monocyclic benzene moiety
- Pyran
- Benzenoid
- Heteroaromatic compound
- Vinylogous acid
- Polyol
- Organoheterocyclic compound
- Oxacycle
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- Organic oxide
- 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 | Solid |
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Experimental Properties | |
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Predicted Properties | |
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General References | - Mennen LI, Sapinho D, Ito H, Galan P, Hercberg S, Scalbert A: Urinary excretion of 13 dietary flavonoids and phenolic acids in free-living healthy subjects - variability and possible use as biomarkers of polyphenol intake. Eur J Clin Nutr. 2008 Apr;62(4):519-25. doi: 10.1038/sj.ejcn.1602744. Epub 2007 Apr 4. [PubMed:17426744 ]
- Rechner AR, Kuhnle G, Hu H, Roedig-Penman A, van den Braak MH, Moore KP, Rice-Evans CA: The metabolism of dietary polyphenols and the relevance to circulating levels of conjugated metabolites. Free Radic Res. 2002 Nov;36(11):1229-41. doi: 10.1080/246-1071576021000016472. [PubMed:12592675 ]
- Martini ND, Katerere DR, Eloff JN: Biological activity of five antibacterial flavonoids from Combretum erythrophyllum (Combretaceae). J Ethnopharmacol. 2004 Aug;93(2-3):207-12. doi: 10.1016/j.jep.2004.02.030. [PubMed:15234754 ]
- Tang HT, Jiang J, Cao Y, Guan PW, Li H, Zhao YJ, Yu J, Tu PF, Li J, Song YL: [Isomeric discrimination of kaempferol versus luteolin by online energy-resolved mass spectrometry]. Zhongguo Zhong Yao Za Zhi. 2021 Jul;46(14):3599-3604. doi: 10.19540/j.cnki.cjcmm.20210302.301. [PubMed:34402283 ]
- Pournaghi N, Khalighi-Sigaroodi F, Safari E, Hajiaghaee R: Bioassay-guided Isolation of Flavonoids from Caesalpinia bonduc (L.) Roxb. and Evaluation of Their Cytotoxicity. Iran J Pharm Res. 2021 Winter;20(1):274-282. doi: 10.22037/ijpr.2020.112557.13824. [PubMed:34400957 ]
- Ruiz de la Bastida A, Peiroten A, Langa S, Alvarez I, Arques JL, Landete JM: Metabolism of flavonoids and lignans by lactobacilli and bifidobacteria strains improves the nutritional properties of flaxseed-enriched beverages. Food Res Int. 2021 Sep;147:110488. doi: 10.1016/j.foodres.2021.110488. Epub 2021 May 31. [PubMed:34399484 ]
- Ma S, Zheng L, Zheng L, Bian X: Data Mining, Network Pharmacology, and Molecular Docking Explore the Effects of Core Traditional Chinese Medicine Prescriptions in Patients with Rectal Cancer and Qi and Blood Deficiency Syndrome. Evid Based Complement Alternat Med. 2021 Aug 2;2021:1353674. doi: 10.1155/2021/1353674. eCollection 2021. [PubMed:34394377 ]
- Khan A, Ali S, Murad W, Hayat K, Siraj S, Jawad M, Khan RA, Uddin J, Al-Harrasi A, Khan A: Phytochemical and pharmacological uses of medicinal plants to treat cancer: A case study from Khyber Pakhtunkhwa, North Pakistan. J Ethnopharmacol. 2021 Aug 12:114437. doi: 10.1016/j.jep.2021.114437. [PubMed:34391861 ]
- Patel DK: Pharmacological activities and Therapeutic potential of kaempferitrin in medicine for the treatment of human disorders: A review of medicinal importance and health benefits. Cardiovasc Hematol Disord Drug Targets. 2021 Aug 12. pii: CHDDT-EPUB-117304. doi: 10.2174/1871529X21666210812111931. [PubMed:34387174 ]
- Xiao HB, Lu XY, Liu ZK, Luo ZF: Kaempferol inhibits the production of ROS to modulate OPN-alphavbeta3 integrin pathway in HUVECs. J Physiol Biochem. 2016 Jun;72(2):303-13. doi: 10.1007/s13105-016-0479-3. Epub 2016 Mar 21. [PubMed:27000882 ]
- Pecio L, Alilou M, Kozachok S, Orhan IE, Eren G, Senol Deniz FS, Stuppner H, Oleszek W: Absolute configuration of spiro-flavostilbenoids from Yucca schidigera Roezl ex Ortgies: First indication of (2R)-naringenin as the key building block. Phytochemistry. 2023 Mar;207:113584. doi: 10.1016/j.phytochem.2022.113584. Epub 2023 Jan 2. [PubMed:36603655 ]
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