Falcarindiol (BioDeep_00000000767)
Secondary id: BioDeep_00000407529
human metabolite PANOMIX_OTCML-2023 Endogenous Antitumor activity
代谢物信息卡片
化学式: C17H24O2 (260.17762039999997)
中文名称: 镰叶芹二醇, 法卡林二醇, 发卡二醇
谱图信息:
最多检出来源 Viridiplantae(plant) 1.06%
分子结构信息
SMILES: C=CC(O)C#CC#CC(O)C=CCCCCCCC
InChI: InChI=1S/C17H24O2/c1-3-5-6-7-8-9-10-14-17(19)15-12-11-13-16(18)4-2/h4,10,14,16-19H,2-3,5-9H2,1H3/b14-10-
描述信息
Constituent of roots of several plants including the common carrot (Daucus carota) and Angelica acutiloba (Dong Dang Gui). Falcarindiol is found in many foods, some of which are wild carrot, carrot, garden tomato (variety), and caraway.
Falcarindiol is found in caraway. Falcarindiol is a constituent of roots of several plants including the common carrot (Daucus carota) and Angelica acutiloba (Dong Dang Gui).
Falcarindiol is a natural product found in Anthriscus nitida, Chaerophyllum aureum, and other organisms with data available.
(+)-(3R,8S)-Falcarindiol is a polyacetylene found in carrots, has antimycobacterial activity, with an IC50 of 6 μM and MIC of 24 μM against Mycobacterium tuberculosis H37Ra[1][2]. Antineoplastic and anti-inflammatory activity[2]. (+)-(3R,8S)-Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
(+)-(3R,8S)-Falcarindiol is a polyacetylene found in carrots, has antimycobacterial activity, with an IC50 of 6 μM and MIC of 24 μM against Mycobacterium tuberculosis H37Ra[1][2]. Antineoplastic and anti-inflammatory activity[2]. (+)-(3R,8S)-Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
(+)-(3R,8S)-Falcarindiol is a polyacetylene found in carrots, has antimycobacterial activity, with an IC50 of 6 μM and MIC of 24 μM against Mycobacterium tuberculosis H37Ra[1][2]. Antineoplastic and anti-inflammatory activity[2]. (+)-(3R,8S)-Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
(+)-(3R,8S)-Falcarindiol is a polyacetylene found in carrots, has antimycobacterial activity, with an IC50 of 6 μM and MIC of 24 μM against Mycobacterium tuberculosis H37Ra[1][2]. Antineoplastic and anti-inflammatory activity[2]. (+)-(3R,8S)-Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
Falcarindiol, an orally active polyacetylenic oxylipin, activates PPARγ and increases the expression of the cholesterol transporter ABCA1 in cells. Falcarindiol induces apoptosis and autophagy. Falcarindiol has anti-inflammatory, antifungal, anticancer and antidiabetic properties[1][2]. Falcarindiol is a click chemistry reagent, it contains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
Falcarindiol, an orally active polyacetylenic oxylipin, activates PPARγ and increases the expression of the cholesterol transporter ABCA1 in cells. Falcarindiol induces apoptosis and autophagy. Falcarindiol has anti-inflammatory, antifungal, anticancer and antidiabetic properties[1][2]. Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
Falcarindiol, an orally active polyacetylenic oxylipin, activates PPARγ and increases the expression of the cholesterol transporter ABCA1 in cells. Falcarindiol induces apoptosis and autophagy. Falcarindiol has anti-inflammatory, antifungal, anticancer and antidiabetic properties[1][2]. Falcarindiol is a click chemistry reagent, itcontains an Alkyne group and can undergo copper-catalyzed azide-alkyne cycloaddition (CuAAc) with molecules containing Azide groups.
同义名列表
20 个代谢物同义名
(Z)-(3S,8S)-Heptadeca-1,9-diene-4,6-diyne-3,8-diol; 1,9-Heptadecadiene-4,6-diyne-3,8-diol, (3R,8S,9Z)-; (Z)-(3R,8S)-Heptadeca-1,9-diene-4,6-diyne-3,8-diol; (3R,8S,9Z)-1,9-Heptadecadiene-4,6-diyne-3,8-diol; (3R,8S,9Z)-heptadeca-1,9-dien-4,6-diyne-3,8-diol; (3r,8s,9z)-heptadeca-1,9-dien-4,6-diyn-3,8-diol; (3R,8S,)-heptadeca-1,9-dien-4,6-diyne-3,8-diol; (9Z)-heptadeca-1,9-dien-4,6-diyne-3,8-diol; Heptadeca-1,9(Z)-diene-4,6-diyne-3,8-diol; heptadeca-1,9-diene-4,6-diyne-3,8-diol; 1,9-Heptadecadiene-4,6-diyne-3,8-diol; QWCNQXNAFCBLLV-YWALDVPYSA-N; (+)-(3R,8S)-Falcarindiol; (3S,8S)-Falcarindiol; (3R,8S)-Falcarindiol; falcarindiol; falcalindiol; FOH 17:6;O; AC1NQY3Z; 3(R),8(S),9(Z)-Falcarindiol
数据库引用编号
20 个数据库交叉引用编号
- KEGG: C08449
- PubChem: 5317309
- PubChem: 5281148
- HMDB: HMDB0033941
- ChEMBL: CHEMBL464796
- ChEMBL: CHEMBL69018
- Wikipedia: Falcarindiol
- LipidMAPS: LMFA05000658
- MeSH: falcarindiol
- KNApSAcK: C00001283
- foodb: FDB012149
- chemspider: 4476194
- CAS: 225110-25-8
- CAS: 55297-87-5
- medchemexpress: HY-N1976
- medchemexpress: HY-N0364
- PMhub: MS000012759
- ChEBI: CHEBI:69236
- PubChem: 10642
- NIKKAJI: J13.068K
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)
47 个相关的物种来源信息
- 48101 - Angelica dahurica:
- 265806 - Angelica japonica:
- 357850 - Angelica keiskei: 10.1016/S0304-3835(03)00466-X
- 312530 - Angelica pubescens:
- 165353 - Angelica sinensis:
- 665671 - Anisotome pilifera: 10.1016/S0305-1978(02)00047-9
- 109081 - Anthriscus nitida: 10.1016/0305-1978(95)00058-5
- 48027 - Anthriscus sylvestris:
- 377493 - Bunium paucifolium: 10.1016/0031-9422(91)83233-B
- 109094 - Chaerophyllum aureum: 10.1515/ZNC-2003-7-818
- 109101 - Chaerophyllum hirsutum: 10.1021/NP040046W
- 48109 - Cicuta virosa:
- 40916 - Crithmum maritimum: 10.1021/NP50099A022
- 1260347 - Cussonia arborea: 10.1055/S-2006-957492
- 1899105 - Cussonia zimmermannii: 10.1021/NP0702133
- 4039 - Daucus carota:
- 4039 - Daucus carota L.: -
- 46395 - Dendropanax arboreus: 10.1021/NP960224O
- 96667 - Eleutherococcus koreanus: 10.1007/BF02857721
- 82096 - Eleutherococcus senticosus: 10.1007/BF02857721
- 371362 - Ferula linkii: 10.1016/0031-9422(93)85291-X
- 48119 - Glehnia littoralis:
- 165499 - Hansenia forbesii: 10.1016/J.BMC.2007.12.021
- 54724 - Hansenia weberbaueriana:
- 99506 - Heracleum candicans: 10.1007/S11418-008-0266-8
- 99507 - Heracleum moellendorffii: 10.1248/BPB.21.257
- 473995 - Heracleum yungningense: 10.1248/CPB.53.701
- 46370 - Heteromorpha arborescens var. abyssinica: 10.1055/S-2006-962326
- 9606 - Homo sapiens: -
- 571622 - Laserpitium gallicum: 10.1016/0031-9422(93)85296-4
- 48042 - Levisticum officinale:
- 54719 - Ligusticum porteri: 10.1002/(SICI)1099-1565(199811/12)9:6<283::AID-PCA419>3.0.CO;2-9
- 1508160 - Ligusticum striatum: 10.1248/CPB.35.4789
- 496675 - Meeboldia yunnanensis:
- 681593 - Niphogeton ternata: 10.1248/CPB.50.115
- 254046 - Oenanthe fistulosa: 10.1021/NP8007717
- 49556 - Oenanthe javanica: 10.1271/BBB.59.526
- 182917 - Oplopanax horridus:
- 54831 - Osmorhiza occidentalis: 10.1021/NP50024A026
- 44588 - Panax quinquefolius: 10.1055/S-2000-8624
- 4043 - Petroselinum crispum: 10.1021/JF00097A003
- 33090 - Plants: -
- 203717 - Saposhnikovia divaricata: 10.1055/S-2000-8624
- 327232 - Schefflera digitata: 10.1055/S-2007-971421
- 4081 - Solanum lycopersicum: 10.1111/J.1439-0434.1984.TB00712.X
- 4111 - Solanum melongena: 10.1104/PP.86.1.176
- 512635 - Thapsia villosa: 10.1016/S0031-9422(00)82550-9
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
- Likang Zhao, Changkai Li, Meng Zhang, Honglian Li, Shengli Ding, Xi Zhao, Lianjuan Yang, Jia Liu, Qing X Li, Risong Na. Design, Synthesis, and Antifungal Activity of Polyacetylenic Alcohol Derivatives and Stereoisomers against Phytopathogenic Fungi.
Journal of agricultural and food chemistry.
2023 Jun; ?(?):. doi:
10.1021/acs.jafc.3c00924
. [PMID: 37261403] - Siyue Kan, Jingwen Tan, Qing Cai, Lulu An, Zhiqin Gao, Hong Yang, Siyu Liu, Risong Na, Lianjuan Yang. Synergistic activity of the combination of falcarindiol and itraconazole in vitro against dermatophytes.
Frontiers in cellular and infection microbiology.
2023; 13(?):1128000. doi:
10.3389/fcimb.2023.1128000
. [PMID: 37207188] - Gokay Albayrak, Serdar Demir, Halil Koyu, Sura Baykan. Anticholinesterase Compounds from Endemic Prangos uechtritzii.
Chemistry & biodiversity.
2022 Nov; 19(11):e202200557. doi:
10.1002/cbdv.202200557
. [PMID: 36201258] - Kyung-Ran Park, Hyun Hee Leem, Yoon-Ju Kwon, Il Keun Kwon, Jin Tae Hong, Hyung-Mun Yun. Falcarindiol Stimulates Apoptotic and Autophagic Cell Death to Attenuate Cell Proliferation, Cell Division, and Metastasis through the PI3K/AKT/mTOR/p70S6K Pathway in Human Oral Squamous Cell Carcinomas.
The American journal of Chinese medicine.
2022; 50(1):295-311. doi:
10.1142/s0192415x22500112
. [PMID: 34931585] - Chaoyue Zhao, Hongda Zheng, Liman Zhou, Hongrui Ji, Lu Zhao, Wengong Yu, Qianhong Gong. Falcarindiol Isolated from Notopterygium incisum Inhibits the Quorum Sensing of Pseudomonas aeruginosa.
Molecules (Basel, Switzerland).
2021 Sep; 26(19):. doi:
10.3390/molecules26195896
. [PMID: 34641440] - Chong-Zhi Wang, Yun Luo, Wei-Hua Huang, Jinxiang Zeng, Chun-Feng Zhang, Mallory Lager, Wei Du, Ming Xu, Chun-Su Yuan. Falcarindiol and dichloromethane fraction are bioactive components in Oplopanax elatus: Colorectal cancer chemoprevention via induction of apoptosis and G2/M cell cycle arrest mediated by cyclin A upregulation.
Journal of applied biomedicine.
2021; 19(2):113-124. doi:
10.32725/jab.2021.013
. [PMID: 34754259] - Corena V Grant, Shengxin Cai, April L Risinger, Huiyun Liang, Barry R O'Keefe, John G Doench, Robert H Cichewicz, Susan L Mooberry. CRISPR-Cas9 Genome-Wide Knockout Screen Identifies Mechanism of Selective Activity of Dehydrofalcarinol in Mesenchymal Stem-like Triple-Negative Breast Cancer Cells.
Journal of natural products.
2020 10; 83(10):3080-3092. doi:
10.1021/acs.jnatprod.0c00642
. [PMID: 33021790] - Mirta Resetar, Xin Liu, Sonja Herdlinger, Olaf Kunert, Eva-Maria Pferschy-Wenzig, Simone Latkolik, Theresa Steinacher, Daniela Schuster, Rudolf Bauer, Verena M Dirsch. Polyacetylenes from Oplopanax horridus and Panax ginseng: Relationship between Structure and PPARγ Activation.
Journal of natural products.
2020 04; 83(4):918-926. doi:
10.1021/acs.jnatprod.9b00691
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Cell.
2020 01; 180(1):176-187.e19. doi:
10.1016/j.cell.2019.11.037
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Fitoterapia.
2019 Oct; 138(?):104355. doi:
10.1016/j.fitote.2019.104355
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Journal of visualized experiments : JoVE.
2019 02; ?(144):. doi:
10.3791/59094
. [PMID: 30799864] - Lucas Busta, Won Cheol Yim, Evan William LaBrant, Peng Wang, Lindsey Grimes, Kiah Malyszka, John C Cushman, Patricia Santos, Dylan K Kosma, Edgar B Cahoon. Identification of Genes Encoding Enzymes Catalyzing the Early Steps of Carrot Polyacetylene Biosynthesis.
Plant physiology.
2018 12; 178(4):1507-1521. doi:
10.1104/pp.18.01195
. [PMID: 30333150] - Lin Xiao, Yuan-Ming Zhou, Xiang-Fei Zhang, Feng-Yu Du. Notopterygium incisum extract and associated secondary metabolites inhibit apple fruit fungal pathogens.
Pesticide biochemistry and physiology.
2018 Sep; 150(?):59-65. doi:
10.1016/j.pestbp.2018.07.001
. [PMID: 30195388] - Morten Kobaek-Larsen, Rime B El-Houri, Lars P Christensen, Issam Al-Najami, Xavier Fretté, Gunnar Baatrup. Dietary polyacetylenes, falcarinol and falcarindiol, isolated from carrots prevents the formation of neoplastic lesions in the colon of azoxymethane-induced rats.
Food & function.
2017 Mar; 8(3):964-974. doi:
10.1039/c7fo00110j
. [PMID: 28197615] - Gai Liu, Daowan Lai, Qi Zhi Liu, Ligang Zhou, Zhi Long Liu. Identification of Nematicidal Constituents of Notopterygium incisum Rhizomes against Bursaphelenchus xylophilus and Meloidogyne incognita.
Molecules (Basel, Switzerland).
2016 Sep; 21(10):. doi:
10.3390/molecules21101276
. [PMID: 27669203] - Wei Sun, Yi-Sheng He, Ling-Hui Xu, Bi-Ying Zhang, Lian-Wen Qi, Jie Yang, Ping Li, Xiao-Dong Wen. Pharmacokinetic profiles of falcarindiol and oplopandiol in rats after oral administration of polyynes extract of Oplopanax elatus.
Chinese journal of natural medicines.
2016 Sep; 14(9):714-720. doi:
10.1016/s1875-5364(16)30085-1
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Phytotherapy research : PTR.
2015 Dec; 29(12):1956-63. doi:
10.1002/ptr.5490
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Molecules (Basel, Switzerland).
2015 Mar; 20(3):3942-54. doi:
10.3390/molecules20033942
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Bioorganic & medicinal chemistry letters.
2015; 25(10):2028-32. doi:
10.1016/j.bmcl.2015.04.003
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Journal of natural products.
2014 Nov; 77(11):2513-21. doi:
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Phytomedicine : international journal of phytotherapy and phytopharmacology.
2013 Aug; 20(11):999-1006. doi:
10.1016/j.phymed.2013.04.013
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Journal of agricultural and food chemistry.
2013 Aug; 61(31):7515-21. doi:
10.1021/jf401042m
. [PMID: 23895038] - Juan David Guzman, Dimitrios Evangelopoulos, Antima Gupta, Jose M Prieto, Simon Gibbons, Sanjib Bhakta. Antimycobacterials from lovage root (Ligusticum officinale Koch).
Phytotherapy research : PTR.
2013 Jul; 27(7):993-8. doi:
10.1002/ptr.4823
. [PMID: 22899555] - Taryn O'Neill, John A Johnson, Duncan Webster, Christopher A Gray. The Canadian medicinal plant Heracleum maximum contains antimycobacterial diynes and furanocoumarins.
Journal of ethnopharmacology.
2013 May; 147(1):232-7. doi:
10.1016/j.jep.2013.03.009
. [PMID: 23501157] - Randi Seljåsen, Gjermund Vogt, Elisabeth Olsen, Per Lea, Lars Arne Høgetveit, Torgeir Tajet, Richard Meadow, Gunnar B Bengtsson. Influence of field attack by carrot psyllid (Trioza apicalis Förster) on sensory quality, antioxidant capacity and content of terpenes, falcarindiol and 6-methoxymellein of carrots (Daucus carota L.).
Journal of agricultural and food chemistry.
2013 Mar; 61(11):2831-8. doi:
10.1021/jf303979y
. [PMID: 23414489] - Atanas G Atanasov, Martina Blunder, Nanang Fakhrudin, Xin Liu, Stefan M Noha, Clemens Malainer, Matthias P Kramer, Amina Cocic, Olaf Kunert, Andreas Schinkovitz, Elke H Heiss, Daniela Schuster, Verena M Dirsch, Rudolf Bauer. Polyacetylenes from Notopterygium incisum--new selective partial agonists of peroxisome proliferator-activated receptor-gamma.
PloS one.
2013; 8(4):e61755. doi:
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Journal of the science of food and agriculture.
2012 Jun; 92(8):1748-54. doi:
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Bioorganic & medicinal chemistry letters.
2012 Apr; 22(8):2927-31. doi:
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Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials.
2012 Feb; 35(2):210-3. doi:
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Molecules (Basel, Switzerland).
2011 Oct; 16(10):8833-47. doi:
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Journal of natural products.
2011 Aug; 74(8):1757-63. doi:
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Rapid communications in mass spectrometry : RCM.
2011 Aug; 25(15):2231-9. doi:
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Phytotherapy research : PTR.
2011 May; 25(5):784-6. doi:
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. [PMID: 21520473] - Tomokazu Ohnuma, Eisaburo Anan, Rika Hoashi, Yuika Takeda, Takahito Nishiyama, Kenichiro Ogura, Akira Hiratsuka. Dietary diacetylene falcarindiol induces phase 2 drug-metabolizing enzymes and blocks carbon tetrachloride-induced hepatotoxicity in mice through suppression of lipid peroxidation.
Biological & pharmaceutical bulletin.
2011; 34(3):371-8. doi:
10.1248/bpb.34.371
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The Journal of pharmacology and experimental therapeutics.
2010 Jun; 333(3):954-60. doi:
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Journal of natural products.
2010 Apr; 73(4):563-7. doi:
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Chemistry & biodiversity.
2010 Mar; 7(3):698-704. doi:
10.1002/cbdv.200900067
. [PMID: 20232332] - Laetitia Meot-Duros, Stéphane Cérantola, Hélène Talarmin, Christophe Le Meur, Gaëtan Le Floch, Christian Magné. New antibacterial and cytotoxic activities of falcarindiol isolated in Crithmum maritimum L. leaf extract.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.
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