Khellin (BioDeep_00000017476)

Main id: BioDeep_00000000750

Secondary id: BioDeep_00000862837

human metabolite PANOMIX_OTCML-2023 blood metabolite Chemicals and Drugs


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 (260.0685)
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。

亚细胞结构定位 关联基因列表
Cytoplasm 9 AHR, ARHGAP45, CYP1A1, EGFR, NLRP3, PIK3CA, PRPF19, PTGS1, PTGS2
Peripheral membrane protein 4 CYP1A1, CYP1B1, PTGS1, PTGS2
Endosome membrane 1 EGFR
Endoplasmic reticulum membrane 5 CYP1A1, CYP1B1, EGFR, PTGS1, PTGS2
Mitochondrion membrane 1 MAOA
Nucleus 6 AHR, EGFR, KDR, NFKBIZ, NLRP3, PRPF19
cytosol 5 AHR, ARHGAP45, MAOA, NLRP3, PIK3CA
dendrite 1 MAOB
nucleoplasm 2 AHR, PRPF19
Cell membrane 3 EGFR, KDR, TNF
Cytoplasmic side 2 MAOA, MAOB
lamellipodium 1 PIK3CA
ruffle membrane 2 ARHGAP45, EGFR
Early endosome membrane 1 EGFR
Golgi apparatus membrane 1 NLRP3
cell junction 2 EGFR, KDR
cell surface 2 EGFR, TNF
glutamatergic synapse 1 EGFR
Golgi apparatus 2 KDR, PTGS1
Golgi membrane 2 EGFR, NLRP3
mitochondrial inner membrane 1 CYP1A1
neuronal cell body 2 MAOB, TNF
Cytoplasm, cytosol 1 NLRP3
endosome 2 EGFR, KDR
plasma membrane 6 ARHGAP45, EGFR, IFNLR1, KDR, PIK3CA, TNF
Membrane 8 ARHGAP45, CYP1B1, EGFR, IFNLR1, LCAT, MAOA, NLRP3, PRPF19
apical plasma membrane 1 EGFR
basolateral plasma membrane 1 EGFR
caveola 1 PTGS2
extracellular exosome 2 LCAT, PTGS1
endoplasmic reticulum 3 KDR, NLRP3, PTGS2
extracellular space 5 EGFR, IL10, IL4, LCAT, TNF
perinuclear region of cytoplasm 2 EGFR, PIK3CA
intercalated disc 1 PIK3CA
mitochondrion 5 CYP1A1, CYP1B1, MAOA, MAOB, NLRP3
protein-containing complex 3 AHR, EGFR, PTGS2
intracellular membrane-bounded organelle 3 CYP1A1, CYP1B1, PTGS1
Microsome membrane 4 CYP1A1, CYP1B1, PTGS1, PTGS2
Single-pass type I membrane protein 2 EGFR, IFNLR1
Secreted 4 IL10, IL4, LCAT, NLRP3
extracellular region 7 ARHGAP45, IL10, IL4, KDR, LCAT, NLRP3, TNF
Mitochondrion outer membrane 2 MAOA, MAOB
Single-pass membrane protein 1 MAOA
mitochondrial outer membrane 2 MAOA, MAOB
[Isoform 2]: Secreted 1 KDR
anchoring junction 1 KDR
transcription regulator complex 1 AHR
photoreceptor outer segment 1 PTGS1
nuclear membrane 1 EGFR
external side of plasma membrane 2 KDR, TNF
high-density lipoprotein particle 1 LCAT
Early endosome 1 KDR
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Cell projection, ruffle membrane 1 ARHGAP45
Mitochondrion inner membrane 1 CYP1A1
Membrane raft 3 EGFR, KDR, TNF
Cytoplasm, cytoskeleton, spindle 1 PRPF19
focal adhesion 1 EGFR
spindle 1 PRPF19
intracellular vesicle 1 EGFR
nuclear speck 2 NFKBIZ, PRPF19
Cytoplasm, cytoskeleton, microtubule organizing center 1 NLRP3
Inflammasome 1 NLRP3
interphase microtubule organizing center 1 NLRP3
NLRP3 inflammasome complex 1 NLRP3
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 2 EGFR, KDR
neuron projection 2 PTGS1, PTGS2
chromatin 1 AHR
phagocytic cup 1 TNF
cytoplasmic ribonucleoprotein granule 1 NFKBIZ
spliceosomal complex 1 PRPF19
site of double-strand break 1 PRPF19
Endomembrane system 2 NLRP3, PTGS1
sorting endosome 1 KDR
Lipid droplet 1 PRPF19
microtubule organizing center 1 NLRP3
aryl hydrocarbon receptor complex 1 AHR
Nucleus, nucleoplasm 1 PRPF19
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
secretory granule lumen 1 ARHGAP45
endoplasmic reticulum lumen 1 PTGS2
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
azurophil granule lumen 1 ARHGAP45
mitochondrial envelope 1 MAOB
Single-pass type IV membrane protein 2 MAOA, MAOB
clathrin-coated endocytic vesicle membrane 1 EGFR
U2-type catalytic step 1 spliceosome 1 PRPF19
catalytic step 2 spliceosome 1 PRPF19
Prp19 complex 1 PRPF19
U2-type catalytic step 2 spliceosome 1 PRPF19
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
nuclear aryl hydrocarbon receptor complex 1 AHR
cytosolic aryl hydrocarbon receptor complex 1 AHR
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
interleukin-28 receptor complex 1 IFNLR1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


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]
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