falcarindiol (BioDeep_00000407529)

Main id: BioDeep_00000000767

Secondary id: BioDeep_00000172512, BioDeep_00000229851

natural product PANOMIX_OTCML-2023 Antitumor activity


代谢物信息卡片


1,9-Heptadecadiene-4,6-diyne-3,8-diol, (3R,8S,9Z)-

化学式: C17H24O2 (260.1776)
中文名称: 镰叶芹二醇, 法卡林二醇
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 37.23%

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

(+)-(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

14 个代谢物同义名

1,9-Heptadecadiene-4,6-diyne-3,8-diol, (3R,8S,9Z)-; (3R,8S,9Z)-heptadeca-1,9-dien-4,6-diyne-3,8-diol; falcarindiol; AIDS-185997; 55297-87-5; AIDS185997; C08449; Heptadeca-1,9-dien-4,6-diyne-3,8-diol; (E,3R,8S)-Heptadeca-1,9-dien-4,6-diyne-3,8-diol; Heptadeca-1,9E-dien-4,6-diyne-3R,8S-diol; (3R,8S)-Falcarindiol; 3(R),8(S),9(Z)-Falcarindiol; (+)-(3R,8S)-Falcarindiol; Falcarindiol



数据库引用编号

37 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)

183 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 14 AIMP2, ALOX5, BCL2, CASP3, HPGDS, NOS2, PPARG, PTGS1, PTGS2, PTTG1, RAD51, SRARP, STAT1, STAT3
Peripheral membrane protein 3 ALOX5, PTGS1, PTGS2
Endoplasmic reticulum membrane 4 ABCA1, BCL2, PTGS1, PTGS2
Nucleus 12 AIMP2, BCL2, CASP3, GABPA, MDC1, NOS2, PPARG, PTTG1, RAD51, SRARP, STAT1, STAT3
cytosol 11 AIMP2, ALOX5, BCL2, CASP3, HPGDS, NOS2, PPARG, PTTG1, RAD51, STAT1, STAT3
dendrite 1 STAT1
nuclear body 1 MDC1
phagocytic vesicle 1 ABCA1
centrosome 1 RAD51
nucleoplasm 10 ALOX5, CASP3, GABPA, HPGDS, MDC1, NOS2, PPARG, RAD51, STAT1, STAT3
RNA polymerase II transcription regulator complex 3 PPARG, STAT1, STAT3
Cell membrane 1 ABCA1
Multi-pass membrane protein 1 ABCA1
cell surface 1 EPCAM
glutamatergic synapse 1 CASP3
Golgi apparatus 2 ABCA1, PTGS1
Golgi membrane 1 INS
neuronal cell body 1 CASP3
Cytoplasm, cytosol 3 AIMP2, ALOX5, NOS2
endosome 1 ABCA1
plasma membrane 4 ABCA1, EPCAM, NOS2, STAT3
Membrane 3 ABCA1, AIMP2, BCL2
apical plasma membrane 1 EPCAM
axon 1 STAT1
basolateral plasma membrane 2 ABCA1, EPCAM
caveola 1 PTGS2
extracellular exosome 2 EPCAM, PTGS1
endoplasmic reticulum 2 BCL2, PTGS2
extracellular space 3 ALOX5, IL6, INS
perinuclear region of cytoplasm 6 ABCA1, ALOX5, NOS2, PPARG, RAD51, STAT1
Cell junction, tight junction 1 EPCAM
bicellular tight junction 1 EPCAM
mitochondrion 2 BCL2, RAD51
protein-containing complex 4 BCL2, PTGS2, RAD51, STAT1
intracellular membrane-bounded organelle 4 ABCA1, HPGDS, PPARG, PTGS1
Microsome membrane 2 PTGS1, PTGS2
postsynaptic density 1 CASP3
Single-pass type I membrane protein 1 EPCAM
Secreted 2 IL6, INS
extracellular region 3 ALOX5, IL6, INS
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
Mitochondrion matrix 1 RAD51
mitochondrial matrix 1 RAD51
transcription regulator complex 1 STAT3
photoreceptor outer segment 1 PTGS1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 RAD51
Nucleus membrane 2 ALOX5, BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 2 ALOX5, BCL2
external side of plasma membrane 1 ABCA1
nucleolus 2 RAD51, STAT1
Cytoplasm, P-body 1 NOS2
P-body 1 NOS2
Cytoplasm, perinuclear region 2 ALOX5, NOS2
Membrane raft 1 ABCA1
pore complex 1 BCL2
focal adhesion 1 MDC1
Peroxisome 1 NOS2
intracellular vesicle 1 ABCA1
peroxisomal matrix 1 NOS2
PML body 1 RAD51
lateral plasma membrane 1 EPCAM
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 1 PPARG
neuron projection 2 PTGS1, PTGS2
chromatin 5 GABPA, PPARG, RAD51, STAT1, STAT3
Chromosome 2 MDC1, RAD51
chromosome, telomeric region 1 RAD51
nuclear chromosome 1 RAD51
site of double-strand break 2 MDC1, RAD51
nuclear envelope 1 ALOX5
Nucleus envelope 1 ALOX5
Endomembrane system 1 PTGS1
endosome lumen 1 INS
lateral element 1 RAD51
myelin sheath 1 BCL2
ficolin-1-rich granule lumen 1 ALOX5
secretory granule lumen 2 ALOX5, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 IL6, INS, PTGS2
nuclear matrix 1 ALOX5
male germ cell nucleus 1 RAD51
endocytic vesicle 1 ABCA1
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
Nucleus matrix 1 ALOX5
nuclear envelope lumen 1 ALOX5
condensed nuclear chromosome 1 RAD51
Lateral cell membrane 1 EPCAM
death-inducing signaling complex 1 CASP3
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
condensed chromosome 1 RAD51
cortical cytoskeleton 1 NOS2
interleukin-6 receptor complex 1 IL6
presynaptic intermediate filament cytoskeleton 1 RAD51
Nucleus intermembrane space 1 ALOX5
BAD-BCL-2 complex 1 BCL2
nuclear ubiquitin ligase complex 1 RAD51
ISGF3 complex 1 STAT1


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. [PMID: 32129622]
  • Ju Eun Jeon, Jung-Gun Kim, Curt R Fischer, Niraj Mehta, Cosima Dufour-Schroif, Kimberly Wemmer, Mary Beth Mudgett, Elizabeth Sattely. A Pathogen-Responsive Gene Cluster for Highly Modified Fatty Acids in Tomato. Cell. 2020 01; 180(1):176-187.e19. doi: 10.1016/j.cell.2019.11.037. [PMID: 31923394]
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  • 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]
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  • 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. [PMID: 21372387]
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  • 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. 2010 Feb; 48(2):553-7. doi: 10.1016/j.fct.2009.11.031. [PMID: 19922760]
  • Ludger Schmiech, Carole Alayrac, Bernhard Witulski, Thomas Hofmann. Structure determination of bisacetylenic oxylipins in carrots (Daucus carota L.) and enantioselective synthesis of falcarindiol. Journal of agricultural and food chemistry. 2009 Nov; 57(22):11030-40. doi: 10.1021/jf9031475. [PMID: 19845355]
  • Stig Purup, Eric Larsen, Lars P Christensen. Differential effects of falcarinol and related aliphatic C(17)-polyacetylenes on intestinal cell proliferation. Journal of agricultural and food chemistry. 2009 Sep; 57(18):8290-6. doi: 10.1021/jf901503a. [PMID: 19694436]
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