| Record Information |
|---|
| Version | 1.0 |
|---|
| Creation date | 2010-04-08 22:04:39 UTC |
|---|
| Update date | 2019-11-26 02:55:07 UTC |
|---|
| Primary ID | FDB000633 |
|---|
| Secondary Accession Numbers | Not Available |
|---|
| Chemical Information |
|---|
| FooDB Name | Kaempferol |
|---|
| Description | Very widespread in the plant world, e.g. in Brassicaceae, Apocynaceae, Dilleniaceae, Ranunculaceae, Leguminosae, etc. Found especies in broccoli, capers, chives, kale, garden cress, fennel, lovage, dill weed and tarragon [CCD]
Kaempferol is a natural flavonol, a type of flavonoid. Many glycosides of kaempferol, such as kaempferitrin and astragalin, have been isolated as natural products from plants. Kaempferol consumption in tea and broccoli has been associated with reduced risk of heart disease. [Wikipedia]. Kaempferol is a biomarker for the consumption of dried and cooked beans. Kaempferol is found in many foods, some of which are peppermint, mexican groundcherry, green zucchini, and wax gourd. |
|---|
| CAS Number | 520-18-3 |
|---|
| Structure | |
|---|
| Synonyms | | Synonym | Source |
|---|
| 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 | | 3,5,7-Trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 9CI | db_source | | 3,5,7-Trihydroxy-2-(4-hydroxyphenyl)chromen-4-one | biospider | | 3,5,7,4'-Tetrahydroxyflavone | biospider | | 4',5,7-Trihydroxyflavonol | db_source | | Kaemferol | biospider | | Kaempferol | db_source | | Kampcetin | biospider | | Pelargidenon | biospider |
|
|---|
| Predicted Properties | |
|---|
| Chemical Formula | C15H10O6 |
|---|
| IUPAC name | 3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one |
|---|
| 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 |
|---|
| InChI Key | IYRMWMYZSQPJKC-UHFFFAOYSA-N |
|---|
| Isomeric SMILES | OC1=CC=C(C=C1)C1=C(O)C(=O)C2=C(O1)C=C(O)C=C2O |
|---|
| Average Molecular Weight | 286.2363 |
|---|
| Monoisotopic Molecular Weight | 286.047738052 |
|---|
| Classification |
|---|
| 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. |
|---|
| Kingdom | Organic compounds |
|---|
| Super Class | Phenylpropanoids and polyketides |
|---|
| Class | Flavonoids |
|---|
| Sub Class | Flavones |
|---|
| Direct Parent | Flavonols |
|---|
| Alternative Parents | |
|---|
| 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
|
|---|
| Molecular Framework | Aromatic heteropolycyclic compounds |
|---|
| External Descriptors | |
|---|
| Ontology |
|---|
|
| Disposition | Route of exposure: Source: Biological location: |
|---|
| Role | Industrial application: |
|---|
| Foods | Cocoa and cocoa products Grains: Nuts and legumes: Fruits and vegetables: Fats and oils: Beverages: |
|---|
| Physico-Chemical Properties - Experimental |
|---|
| Physico-Chemical Properties - Experimental | | Property | Value | Reference |
|---|
| Physical state | Solid | |
|---|
| Physical Description | Not Available | |
|---|
| Mass Composition | C 62.94%; H 3.52%; O 33.54% | DFC |
|---|
| Melting Point | Mp 276-278° | DFC |
|---|
| Boiling Point | Not Available | |
|---|
| Experimental Water Solubility | Not Available | |
|---|
| Experimental logP | Not Available | |
|---|
| Experimental pKa | Not Available | |
|---|
| Isoelectric point | Not Available | |
|---|
| Charge | Not Available | |
|---|
| Optical Rotation | Not Available | |
|---|
| Spectroscopic UV Data | 365 () (EtOH) (Berdy) | DFC |
|---|
| Density | Not Available | |
|---|
| Refractive Index | Not Available | |
|---|
|
|---|
| Spectra |
|---|
| Spectra | | Spectrum Type | Description | Splash Key | View |
|---|
| GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized) | splash10-0079-1963700000-1d3775db7c536f63b70c | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (5 TMS) | splash10-0bt9-0000290000-4a7068686e907a319864 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-000i-4290000000-ccb984ce16e32c25d878 | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0079-1963700000-1d3775db7c536f63b70c | JSpectraViewer | MoNA | | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0bt9-0000290000-4a7068686e907a319864 | JSpectraViewer | MoNA | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-052r-0590000000-3bfd778520b9c39bc4ba | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-0mc0-2150190000-3a2826fb2ce8460675bc | JSpectraViewer | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-000i-0090000000-f0101bac1cb6491794f5 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-000i-0690000000-3afcadc746823bc03ebd | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0v4i-5900000000-6a870572cf8a486dd6b7 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - EI-B (JEOL JMS-06-H) , Positive | splash10-000i-4290000000-75bfe61cc0a42797e86a | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positive | splash10-000i-0090000000-ead9f201b8c5b6b6e46e | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-000i-0190000000-2bc892de84e0225a49cf | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-052u-1930000000-08779ff26cd586d78e41 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-0udr-0920000000-97d144af795812440c46 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-000i-0290000000-5573e7fd91cf25805a11 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-014s-2920000000-397e01f2d2cf07025409 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-014i-1920000000-891ca58b63b857f31594 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negative | splash10-0079-0090040000-5111d04af3f3d3e053c7 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-000i-0950000000-580cab3c0e471a3f4e00 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-000i-0950000000-580cab3c0e471a3f4e00 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 50V, Negative | splash10-066r-0930000000-f40d69c592d60004cae0 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 20V, Negative | splash10-066r-0930000000-f40d69c592d60004cae0 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 40V, Negative | splash10-000i-0950000000-580cab3c0e471a3f4e00 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF , Negative | splash10-000i-0091000000-295f056c177e6e49fb6b | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - ESI-TOF 50V, Negative | splash10-066r-0930000000-f40d69c592d60004cae0 | JSpectraViewer | MoNA | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0090000000-0d8eaf63d3860cdc1cbf | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-000i-0090000000-3969010f013a967001da | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0gbi-6790000000-5668e7d87a859b519804 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-000i-0090000000-4cba2efdae1d7d094e17 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-000i-0190000000-489c309b159fce3df0d6 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-001i-4950000000-9d8aab7149b59126c14a | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
|
|---|
| External Links |
|---|
| ChemSpider ID | 4444395 |
|---|
| ChEMBL ID | CHEMBL150 |
|---|
| KEGG Compound ID | C05903 |
|---|
| Pubchem Compound ID | 5280863 |
|---|
| Pubchem Substance ID | Not Available |
|---|
| ChEBI ID | Not Available |
|---|
| Phenol-Explorer ID | 290 |
|---|
| DrugBank ID | DB01852 |
|---|
| HMDB ID | HMDB05801 |
|---|
| CRC / DFC (Dictionary of Food Compounds) ID | BFG98-E:BFG98-E |
|---|
| EAFUS ID | Not Available |
|---|
| Dr. Duke ID | 3,5,7,4'-TETRAHYDROXYFLAVONE|KAEMPFEROL |
|---|
| BIGG ID | Not Available |
|---|
| KNApSAcK ID | C00004565 |
|---|
| HET ID | KMP |
|---|
| Food Biomarker Ontology | Not Available |
|---|
| VMH ID | Not Available |
|---|
| Flavornet ID | Not Available |
|---|
| GoodScent ID | Not Available |
|---|
| SuperScent ID | Not Available |
|---|
| Wikipedia ID | Kaempferol |
|---|
| Phenol-Explorer Metabolite ID | 290 |
|---|
| Duplicate IDS | Not Available |
|---|
| Old DFC IDS | Not Available |
|---|
| Associated Foods |
|---|
| Food | Content Range | Average | Reference |
|---|
| Food | | | Reference |
|---|
|
| Biological Effects and Interactions |
|---|
| Health Effects / Bioactivities | | Descriptor | ID | Definition | Reference |
|---|
| 11beta-hydroxysteroid-dehydrogenase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | | 5-lipoxygenase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | | aldose reductase inhibitor | 48550 | An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21). | DUKE | | anti aflatoxin | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | | anti aggregant | | | DUKE | | anti allergic | 50857 | A drug used to treat allergic reactions. | DUKE | | anti bacterial | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | | anti cancer | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti fertility | | | DUKE | | anti gingivitic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti herpetic | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | | anti histaminic | 37956 | Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists. | DUKE | | anti implantation | | | DUKE | | anti inflammatory | 35472 | A substance that reduces or suppresses inflammation. | DUKE | | anti leukemic | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti lymphocytic | | | DUKE | | anti mutagenic | | | DUKE | | antioxidant | 22586 | A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324. | DUKE | | anti periodontic | | | DUKE | | anti plaque | | | DUKE | | anti radicular | | | DUKE | | anti septic | 33281 | A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. | DUKE | | anti serotonin | 48278 | | DUKE | | anti spasmodic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | anti staphylococcic | 33282 | A substance that kills or slows the growth of bacteria. | DUKE | | antitumor | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | antitumor promoter | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | anti ulcer | 49201 | One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract. | DUKE | | anti viral | 22587 | A substance that destroys or inhibits replication of viruses. | DUKE | | apoptotic | | | DUKE | | aromatase inhibitor | 50790 | An EC 1.14.14.* (oxidoreductase acting on paired donors, incorporating of 1 atom of oxygen, with reduced flavin or flavoprotein as one donor) inhibitor which interferes with the action of aromatase (EC 1.14.14.14) and so reduces production of estrogenic steroid hormones. | DUKE | | cAMP-phosphodiesterase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | | cancer preventive | 35610 | A substance that inhibits or prevents the proliferation of neoplasms. | DUKE | | carcinogenic | 50903 | A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities. | DUKE | | choleretic | | | DUKE | | copper chelator | 38161 | A ligand with two or more separate binding sites that can bind to a single metallic central atom, forming a chelate. | DUKE | | cyclooxygenase-2 inhibitor | 50629 | A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2. | DUKE | | cyclooxygenase inhibitor | 35544 | A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes. | DUKE | | cytotoxic | 52209 | A role played by the molecular entity or part thereof which causes the development of a pathological process. | DUKE | | diaphoretic | | | DUKE | | diuretic | 35498 | An agent that promotes the excretion of urine through its effects on kidney function. | DUKE | | estrogenic | | | DUKE | | fungicide | 24127 | A substance used to destroy fungal pests. | DUKE | | hepatoprotective | 62868 | Any compound that is able to prevent damage to the liver. | DUKE | | HIV-reverse-transcriptase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | | hypotensive | | | DUKE | | ICAM-1 inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | | iNOS inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | | inotropic | | | DUKE | | iodothyronine-deiodinase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | | JNK inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | | lipoxygenase inhibitor | 35856 | A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes. | DUKE | | monoamine-oxidase inhibitor | 23924 | A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. | DUKE | | mutagenic | | | DUKE | | natriuretic | | | DUKE | | neuroprotective | 63726 | Any compound that can be used for the treatment of neurodegenerative disorders. | DUKE | | nitric-oxide inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | | platelet aggregation factor inhibitor | 50427 | A drug or agent which antagonizes or impairs any mechanism leading to blood platelet aggregation, whether during the phases of activation and shape change or following the dense-granule release reaction and stimulation of the prostaglandin-thromboxane system. | DUKE | | pesticide | 25944 | Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. | DUKE | | protisticide | | | DUKE | | quinone-reductase inducer | | | DUKE | | teratologic | | | DUKE | | TNF-alpha inhibitor | 35222 | A substance that diminishes the rate of a chemical reaction. | DUKE | | topoisomerase-II inhibitor | 50750 | A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (topoisomerase II), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands. | DUKE | | topoisomerase-I inhibitor | 50276 | A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA. | DUKE | | tyrosinase inhibitor | 59997 | Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals. | DUKE | | utero trophic | 52217 | Any substance introduced into a living organism with therapeutic or diagnostic purpose. | DUKE | | vasodilator | 35620 | A drug used to cause dilation of the blood vessels. | DUKE |
|
|---|
| Enzymes | Not Available |
|---|
| Pathways | Not Available |
|---|
| Metabolism | Not Available |
|---|
| Biosynthesis | Not Available |
|---|
| Organoleptic Properties |
|---|
| Flavours | | Flavor | Citations |
|---|
| bitter |
- Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
|
|
|---|
| Files |
|---|
| MSDS | show |
|---|
| References |
|---|
| Synthesis Reference | Not Available |
|---|
| General Reference | Not Available |
|---|
| Content Reference | — Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
|
|---|
