Khellin (BioDeep_00000017476)

Main id: BioDeep_00000000750

Secondary id: BioDeep_00000862837

human metabolite PANOMIX_OTCML-2023 blood metabolite Chemicals and Drugs Volatile Flavor Compounds


代谢物信息卡片


InChI=1/C14H12O5/c1-7-6-9(15)10-11(16-2)8-4-5-18-12(8)14(17-3)13(10)19-7/h4-6H,1-3H3

化学式: C14H12O5 (260.0684702)
中文名称: 呋喃并色酮, 凯林
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C12C(=O)C=C(C)OC=1C(OC)=C1C(C=CO1)=C2OC
InChI: InChI=1S/C14H12O5/c1-7-6-9(15)10-11(16-2)8-4-5-18-12(8)14(17-3)13(10)19-7/h4-6H,1-3H3

描述信息

Khellin is a furanochrome in which the basic tricyclic skeleton is substituted at positions 4 and 9 with methoxy groups and at position 7 with a methyl group. A major constituent of the plant Ammi visnaga it is a herbal folk medicine used for various illnesses, its main effect being as a vasodilator. It has a role as a vasodilator agent, a bronchodilator agent, an anti-asthmatic agent and a cardiovascular drug. It is an organic heterotricyclic compound, an oxacycle and a furanochromone. It is functionally related to a 5H-furo[3,2-g]chromen-5-one.
Khellin is a natural product found in Ammi visnaga, Annona muricata, and other organisms with data available.
A vasodilator that also has bronchodilatory action. It has been employed in the treatment of angina pectoris, in the treatment of asthma, and in conjunction with ultraviolet light A, has been tried in the treatment of vitiligo. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1024)
See also: Visnaga daucoides fruit (part of).
D019141 - Respiratory System Agents > D018927 - Anti-Asthmatic Agents > D001993 - Bronchodilator Agents
D011838 - Radiation-Sensitizing Agents > D017319 - Photosensitizing Agents > D011564 - Furocoumarins
D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents
D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents
Khellin is a furochromone that can be isolated from Ammi visnuga L.. Khellin is an EGFR inhibitor with an IC50 of 0.15 μM. Khelline has anti-proliferative activity in vitro. Khellin has antispasmodic and coronary vasodilator effects[1][2].
Khellin is a furochromone that can be isolated from Ammi visnuga L.. Khellin is an EGFR inhibitor with an IC50 of 0.15 μM. Khelline has anti-proliferative activity in vitro. Khellin has antispasmodic and coronary vasodilator effects[1][2].

同义名列表

132 个代谢物同义名

InChI=1/C14H12O5/c1-7-6-9(15)10-11(16-2)8-4-5-18-12(8)14(17-3)13(10)19-7/h4-6H,1-3H3; 5H-Furo[3,2-g][1]benzopyran-5-one, 4,9-dimethoxy-7-methyl-; 5H-Furo(3,2-g)(1)benzopyran-5-one, 4,9-dimethoxy-7-methyl-; 4,9-Dimethoxy-7-methyl-5H-furo[3,2-g]-[1]benzopyran-5-one; 4,9-Dimethoxy-7-methyl-5H-furo[3,2-g][1]benzopyran-5-one; 4,9-Dimethoxy-7-methyl-5H-furo(3,2-g)(1)benzopyran-5-one; 4,9-Dimethoxy-7-methyl-5-oxofuro(3,2-g)-1,2-chromene; 4,9-Dimethoxy-7-methyl-5-oxofuro(3,2-g)(1)benzopyran; 4,9-Dimethoxy-7-methyl-5H-furo[3,2-g]chromen-5-one #; 4,9-Dimethoxy-7-methyl-5-oxo-1,8-dioxabenz-(f)indene; 4,9-dimethoxy-7-methylpyrano[3,2-f][1]benzoxol-5-one; 4,9-dimethoxy-7-methyl-5H-furo(3,2-g)chromen-5-one; 4,9-Dimethoxy-7-methyl-5H-furo[3,2-g]chromen-5-one; 5,9-dimethoxy-2-methylfurano[3,2-g]chromen-4-one; 4,9-Dimethoxy-7-methyl-furo[3,2-g]chromen-5-one; 5,8-Dimethoxy-2-methyl-4,5-furano-6,7-chromone; 4,9-dimethoxy-7-methylfuro[3,2-g]chromen-5-one; 5,8-Dimethoxy-2-methyl-4,5-furo-6,7-chromone; 5-19-06-00320 (Beilstein Handbook Reference); 5,8-Dimethoxy-2-methyl-6,7-furanochromone; 5H-Furo[3, 4,9-dimethoxy-7-methyl-; Khellin, analytical standard; HSMPDPBYAYSOBC-UHFFFAOYSA-; 4,2-g][1]benzopyran-5-one; 4,8-dioxabenz-[f]indene; Khellin, for microscopy; 5,5-furano-6,7-chromone; Khelline [INN-French]; 5,5-furo-6,7-chromone; Quelina [INN-Spanish]; Khellinum [INN-Latin]; 4,2-g]-1,2-chromene; 4,2-g][1]benzopyran; 5,7-furanochromone; Chellina [Italian]; Prestwick1_000091; Prestwick2_000091; Prestwick3_000091; Khellin [INN:DCF]; Prestwick0_000091; Spectrum5_000154; Spectrum4_001557; KHELLIN [WHO-DD]; Spectrum2_000593; Spectrum3_000654; KHELLIN (MART.); KHELLIN [MART.]; UNII-5G117T0TJZ; Cardio-khellin; Tox21_110374_1; MEGxp0_000331; KHELLIN [INN]; DivK1c_000046; BPBio1_000048; Ammi-khellin; KBio2_005615; ACon1_000350; KBio1_000046; KBio2_003047; Simeskellina; Ammivisnagen; KHELLIN [MI]; KBio2_000479; ACon0_000983; Tox21_110374; Interkhellin; KBio3_001507; Ammispasmin; Gynokhellan; Gynokhellin; Ammicardine; IDI1_000046; Vasokellina; Intercellin; CAS-82-02-0; Chorafurone; Interkellin; Khellanals; Bi-Kellina; Corafurone; Benecardin; Khellamine; Visammimix; Khelline I; Khellinorm; Benekardin; 5G117T0TJZ; Medekellin; Amicardine; Methafrone; Visnagalin; Kelicorin; Khellinum; Amikellin; Viscardan; Ammipuran; AI3-52114; Viscardin; Khelangin; Kalangin; Khelloyd; Kellosal; Khelfren; Chellina; Lynamine; Visammin; Kelourin; Hkelfren; Khelline; Mefurina; Kelincor; Vismagen; Khelisem; Visnagen; Rykellin; Coronin; Kelicor; Quelina; Khellin; Chellin; Amiptan; Ammivin; Kelamin; Kellina; Norkel; Kellin; kelina; Keloid; Eskel; Khell; Khellin; Khellin



数据库引用编号

19 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

9 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Martin Ndayambaje, Hicham Wahnou, Marieme Sow, Oumaima Chgari, Thierry Habyarimana, Mehdi Karkouri, Youness Limami, Abdallah Naya, Mounia Oudghiri. Exploring the multifaceted effects of Ammi visnaga: subchronic toxicity, antioxidant capacity, immunomodulatory, and anti-inflammatory activities. Journal of toxicology and environmental health. Part A. 2024 Feb; 87(4):150-165. doi: 10.1080/15287394.2023.2289430. [PMID: 38037686]
  • Veselina Adımcılar, Neslihan Beyazit, F Bedia Erim. Khellin and visnagin in different organs of Ammi visnaga and Ammi majus. Natural product research. 2023 Jan; 37(1):164-166. doi: 10.1080/14786419.2021.1956924. [PMID: 34569361]
  • X-L Rao, L-L Liu, J Huang, J Chen. Neuroprotective effects of visnagin on cerebral ischemia-reperfusion injury rats and the underlying mechanisms. European review for medical and pharmacological sciences. 2022 06; 26(12):4371-4379. doi: 10.26355/eurrev_202206_29076. [PMID: 35776038]
  • Fatma Abd El-Fattah Ragab, Yassin Mohammed Nissan, M Alaraby Salem, Mamdouh Moawad Ali, Ahmed Abbass Mohamed Abdelrahman Selim. Non-ulcerogenic pyrazolyl 2-hydroxychalcones and pyrazolylpyrazolines derived from naturally existing furochromone (khellin): semi-synthesis, docking study and anti-inflammatory activity. Natural product research. 2022 May; 36(10):2486-2494. doi: 10.1080/14786419.2021.1907383. [PMID: 33813964]
  • Giulia Vanti, Lucrezia Muti, Mario D'Ambrosio, Lucia Grifoni, Maria Camilla Bergonzi, Cristina Luceri, Anna Rita Bilia. Nanostructured Lipid Carriers Can Enhance Oral Absorption of Khellin, a Natural Pleiotropic Molecule. Molecules (Basel, Switzerland). 2021 Dec; 26(24):. doi: 10.3390/molecules26247657. [PMID: 34946734]
  • Mohammad H Abukhalil, Omnia E Hussein, Saleem H Aladaileh, Osama Y Althunibat, Wesam Al-Amarat, Sultan A Saghir, Manal A Alfwuaires, Abdulmohsen I Algefare, Khalid M Alanazi, Farhan K Al-Swailmi, Emadeldin M Kamel, Ayman M Mahmoud. Visnagin prevents isoproterenol-induced myocardial injury by attenuating oxidative stress and inflammation and upregulating Nrf2 signaling in rats. Journal of biochemical and molecular toxicology. 2021 Nov; 35(11):e22906. doi: 10.1002/jbt.22906. [PMID: 34486204]
  • Sonali S Bharate. Enhancing Biopharmaceutical Attributes of Khellin by Amorphous Binary Solid Dispersions. AAPS PharmSciTech. 2021 Oct; 22(8):260. doi: 10.1208/s12249-021-02126-3. [PMID: 34705156]
  • Laura Risaliti, Xuan Yu, Giulia Vanti, Maria Camilla Bergonzi, Meng Wang, Anna Rita Bilia. Hydroxyethyl cellulose hydrogel for skin delivery of khellin loaded in ascosomes: Characterization, in vitro/in vivo performance and acute toxicity. International journal of biological macromolecules. 2021 May; 179(?):217-229. doi: 10.1016/j.ijbiomac.2021.02.206. [PMID: 33662425]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Jaime Piquero-Casals, Laura Martínez-Martínez, Agustín Alomar, Eduardo Rozas-Muñoz, Candido Juarez, Luis Puig. LRP1/CD91 is highly expressed in monocytes from patients with vitiligo - even after repigmentation. Experimental dermatology. 2021 03; 30(3):390-395. doi: 10.1111/exd.14249. [PMID: 33249636]
  • Noha Khalil, Mokhtar Bishr, Mohamed El-Degwy, Mohamed Abdelhady, Mohamed Amin, Osama Salama. Assessment of Conventional Solvent Extraction vs. Supercritical Fluid Extraction of Khella (Ammi visnaga L.) Furanochromones and Their Cytotoxicity. Molecules (Basel, Switzerland). 2021 Feb; 26(5):. doi: 10.3390/molecules26051290. [PMID: 33673560]
  • Jamaan S Ajarem, Ahmad K Hegazy, Gamal A Allam, Ahmed A Allam, Saleh N Maodaa, Ayman M Mahmoud. Effect of Visnagin on Altered Steroidogenesis and Spermatogenesis, and Testicular Injury Induced by the Heavy Metal Lead. Combinatorial chemistry & high throughput screening. 2021; 24(6):758-766. doi: 10.2174/1386207323999200918124639. [PMID: 32957877]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Lakshmi Priya Pasari, Amit Khurana, Pratibha Anchi, Mohd Aslam Saifi, Shivaraju Annaldas, Chandraiah Godugu. Visnagin attenuates acute pancreatitis via Nrf2/NFκB pathway and abrogates associated multiple organ dysfunction. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2019 Apr; 112(?):108629. doi: 10.1016/j.biopha.2019.108629. [PMID: 30798137]
  • Fatma Aydoğmuş-Öztürk, Humera Jahan, Neslihan Beyazit, Keriman Günaydın, Muhammad Iqbal Choudhary. The anticancer activity of visnagin, isolated from Ammi visnaga L., against the human malignant melanoma cell lines, HT 144. Molecular biology reports. 2019 Apr; 46(2):1709-1714. doi: 10.1007/s11033-019-04620-1. [PMID: 30694454]
  • Prashant Joshi, Vinay R Sonawane, Ibidapo S Williams, Glen J P McCann, Linda Gatchie, Rajni Sharma, Naresh Satti, Bhabatosh Chaudhuri, Sandip B Bharate. Identification of karanjin isolated from the Indian beech tree as a potent CYP1 enzyme inhibitor with cellular efficacy via screening of a natural product repository. MedChemComm. 2018 Feb; 9(2):371-382. doi: 10.1039/c7md00388a. [PMID: 30108931]
  • Maria L Travaini, Gustavo M Sosa, Eduardo A Ceccarelli, Helmut Walter, Charles L Cantrell, Nestor J Carrillo, Franck E Dayan, Kumudini M Meepagala, Stephen O Duke. Khellin and Visnagin, Furanochromones from Ammi visnaga (L.) Lam., as Potential Bioherbicides. Journal of agricultural and food chemistry. 2016 Dec; 64(50):9475-9487. doi: 10.1021/acs.jafc.6b02462. [PMID: 27936681]
  • Roman Pavela, Naděžda Vrchotová, Jan Tříska. Larvicidal activity of extracts from Ammi visnaga Linn. (Apiaceae) seeds against Culex quinquefasciatus Say. (Diptera: Culicidae). Experimental parasitology. 2016 Jun; 165(?):51-7. doi: 10.1016/j.exppara.2016.03.016. [PMID: 26995534]
  • Jihan M Badr, Ghada M Hadad, Khaled Nahriry, Hashem A Hassanean. Validated HPLC method for simultaneous estimation of khellol glucoside, khellin and visnagin in Ammi visnaga L. fruits and pharmaceutical preparations. Natural product research. 2015; 29(7):593-601. doi: 10.1080/14786419.2014.945170. [PMID: 25111086]
  • Isa Kilicaslan, Selcuk Coskun. Spontaneous stone passage: is it Ammi visnaga effect?. Urological research. 2012 Dec; 40(6):799-800. doi: 10.1007/s00240-012-0509-8. [PMID: 22990409]
  • Karin G Haug, Benjamin Weber, Guenther Hochhaus, Veronika Butterweck. Pharmacokinetic evaluation of visnagin and Ammi visnaga aqueous extract after oral administration in rats. Planta medica. 2012 Nov; 78(17):1831-6. doi: 10.1055/s-0032-1315393. [PMID: 23096256]
  • Mi-Sun Koo, Selvakumar Subbian, Gilla Kaplan. Strain specific transcriptional response in Mycobacterium tuberculosis infected macrophages. Cell communication and signaling : CCS. 2012 Jan; 10(1):2. doi: 10.1186/1478-811x-10-2. [PMID: 22280836]
  • Karin G Haug, Benjamin Weber, Guenther Hochhaus, Veronika Butterweck. Nonlinear pharmacokinetics of visnagin in rats after intravenous bolus administration. European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences. 2012 Jan; 45(1-2):79-89. doi: 10.1016/j.ejps.2011.10.023. [PMID: 22085634]
  • Lei Lei, Shundai Li, Ying Gu. Cellulose synthase complexes: composition and regulation. Frontiers in plant science. 2012; 3(?):75. doi: 10.3389/fpls.2012.00075. [PMID: 22639663]
  • Suwittra Chaemchuen, Suang Rungpragayphan, Yong Poovorawan, Kanitha Patarakul. Identification of candidate host proteins that interact with LipL32, the major outer membrane protein of pathogenic Leptospira, by random phage display peptide library. Veterinary microbiology. 2011 Nov; 153(1-2):178-85. doi: 10.1016/j.vetmic.2011.04.030. [PMID: 21592685]
  • Aslam Khan, Samra Bashir, Saeed R Khan, Anwar H Gilani. Antiurolithic activity of Origanum vulgare is mediated through multiple pathways. BMC complementary and alternative medicine. 2011 Oct; 11(?):96. doi: 10.1186/1472-6882-11-96. [PMID: 22004514]
  • P Vanachayangkul, N Chow, S R Khan, Veronika Butterweck. Prevention of renal crystal deposition by an extract of Ammi visnaga L. and its constituents khellin and visnagin in hyperoxaluric rats. Urological research. 2011 Jun; 39(3):189-95. doi: 10.1007/s00240-010-0333-y. [PMID: 21069311]
  • Jean Matthieu Prot, Anne-Sophie Briffaut, Franck Letourneur, Philippe Chafey, Franck Merlier, Yves Grandvalet, Cécile Legallais, Eric Leclerc. Integrated proteomic and transcriptomic investigation of the acetaminophen toxicity in liver microfluidic biochip. PloS one. 2011; 6(8):e21268. doi: 10.1371/journal.pone.0021268. [PMID: 21857903]
  • Angelo Aquino, Grazia Graziani, Ornella Franzese, Salvatore P Prete, Enzo Bonmassar, Laura Bonmassar, Stefania D'Atri. Exogenous control of the expression of Group I CD1 molecules competent for presentation of microbial nonpeptide antigens to human T lymphocytes. Clinical & developmental immunology. 2011; 2011(?):790460. doi: 10.1155/2011/790460. [PMID: 21603161]
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  • Wayne Chadwick, Randall Brenneman, Bronwen Martin, Stuart Maudsley. Complex and multidimensional lipid raft alterations in a murine model of Alzheimer's disease. International journal of Alzheimer's disease. 2010 Dec; 2010(?):604792. doi: 10.4061/2010/604792. [PMID: 21151659]
  • Dongmin Shao, Anthony W Segal, Lodewijk V Dekker. Subcellular localisation of the p40phox component of NADPH oxidase involves direct interactions between the Phox homology domain and F-actin. The international journal of biochemistry & cell biology. 2010 Oct; 42(10):1736-43. doi: 10.1016/j.biocel.2010.07.009. [PMID: 20637895]
  • James R Bamburg, Barbara W Bernstein. Roles of ADF/cofilin in actin polymerization and beyond. F1000 biology reports. 2010 Aug; 2(?):62. doi: 10.3410/b2-62. [PMID: 21173851]
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  • Lauren G MacNeil, Simon Melov, Alan E Hubbard, Steven K Baker, Mark A Tarnopolsky. Eccentric exercise activates novel transcriptional regulation of hypertrophic signaling pathways not affected by hormone changes. PloS one. 2010 May; 5(5):e10695. doi: 10.1371/journal.pone.0010695. [PMID: 20502695]
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  • Reiko Minakami, Yuichi Maehara, Sachiko Kamakura, Osamu Kumano, Kei Miyano, Hideki Sumimoto. Membrane phospholipid metabolism during phagocytosis in human neutrophils. Genes to cells : devoted to molecular & cellular mechanisms. 2010 May; 15(5):409-24. doi: 10.1111/j.1365-2443.2010.01393.x. [PMID: 20384786]
  • Jovita Ponce, David Brea, Montserrat Carrascal, Verónica Guirao, Nuria Degregorio-Rocasolano, Tomás Sobrino, José Castillo, Antonio Dávalos, Teresa Gasull. The effect of simvastatin on the proteome of detergent-resistant membrane domains: decreases of specific proteins previously related to cytoskeleton regulation, calcium homeostasis and cell fate. Proteomics. 2010 May; 10(10):1954-65. doi: 10.1002/pmic.200900055. [PMID: 20217863]
  • Silvia Volpe, Sylvia Thelen, Thomas Pertel, Martin J Lohse, Marcus Thelen. Polarization of migrating monocytic cells is independent of PI 3-kinase activity. PloS one. 2010 Apr; 5(4):e10159. doi: 10.1371/journal.pone.0010159. [PMID: 20419163]
  • Yuqing Wang, Yingfang Zhu, Yu Ling, Haiyan Zhang, Peng Liu, Frantisek Baluska, Jozef Samaj, Jinxing Lin, Qinli Wang. Disruption of actin filaments induces mitochondrial Ca2+ release to the cytoplasm and [Ca2+]c changes in Arabidopsis root hairs. BMC plant biology. 2010 Mar; 10(?):53. doi: 10.1186/1471-2229-10-53. [PMID: 20334630]
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  • Pattaraporn Vanachayangkul, Veronika Butterweck, Reginald F Frye. Determination of visnagin in rat plasma by liquid chromatography with tandem mass spectrometry and its application to in vivo pharmacokinetic studies. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2009 Mar; 877(7):653-6. doi: 10.1016/j.jchromb.2009.01.014. [PMID: 19188097]
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