alpha-Farnesene (BioDeep_00000000722)

Main id: BioDeep_00000859692

Secondary id: BioDeep_00001891810

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


3,7,11-Trimethyl-1,3,6,10-dodecatetraene, (trans,trans)-

化学式: C15H24 (204.1878)
中文名称: α-法呢烯, 金合欢烯,异构体混合物, 金合欢烯, α-法呢烯
谱图信息: 最多检出来源 Homo sapiens(feces) 52.09%

分子结构信息

SMILES: C=C/C(=C/C/C=C(\C)/CCC=C(C)C)/C
InChI: InChI=1S/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9-10,12H,1,7-8,11H2,2-5H3/b14-10+,15-12+

描述信息

alpha-Farnesene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (3E,6E)-alpha-Farnesene, also known as trans-alpha-Farnesene, is a sweet, bergamot, and citrus tasting flavouring ingredient. (3E,6E)-alpha-Farnesene is a constituent of the natural coating of apples and pears and other fruit. It has been identified in gingers, cottonseeds, common oregano, sweet oranges, spearmints, guava, pomes, and pears. This could make (3E,6E)-alpha-farnesene a potential biomarker for the consumption of these foods.
Alpha-farnesene is a farnesene that is 1,3,6,10-tetraene substituted by methyl groups at positions 3, 7 and 11 respectively.
alpha-Farnesene is a natural product found in Eupatorium cannabinum, Lonicera japonica, and other organisms with data available.
See also: Chamomile (part of); Cannabis sativa subsp. indica top (part of).
Constituent of the natural coating of apples and pears and other fruit. Flavouring ingredient. (3E,6E)-alpha-Farnesene is found in many foods, some of which are cottonseed, spearmint, ginger, and fruits.

同义名列表

62 个代谢物同义名

3,7,11-Trimethyl-1,3,6,10-dodecatetraene, (trans,trans)-; 1,3,6,10-Dodecatetraene, 3,7,11-trimethyl-, (3E,6E)-; 1,3,6,10-Dodecatetraene, 3,7,11-trimethyl-, (E,E)-; (3E,6E)-3,7,11-Trimethyl-1,3,6,10-dodecatetraene #; (3E,6E)-3,7,11-trimethyl-dodeca-1,3,6,10-tetraene; (3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene; (3E,6E)-3,7,11-Trimethyl-1,3,6,10-dodecatetraene; 2,6,10-Trimethyl-2,6,9,11-dodecatetraene, trans-; trans-2,6,10-Trimethyl-2,6,9,11-dodecatetraene; 3,7,11-Trimethyl-(E,E)-1,3,6,10-dodecatetraene; trans-3,7,11-Trimethyl-1,3,6,10-dodecatetraene; 1,3,6,10-Dodecatetraene, 3,7,11-trimethyl-; 3,7,11-Trimethyl-dodeca-1,3,6,10-tetraene; 3,7,11-Trimethyl-1,3,6,10-dodecatetraene; 2,6,10-Trimethyldodeca-2,6,9,11-tetraene; 3,7,11-trimethyldodeca-1,3,6,10-tetraene; trans,trans-.alpha.-Farnesene; .alpha.-trans,trans-Farnesene; .alpha.-Farnesene (isomer 1); alpha-trans,trans-Farnesene; trans,trans-alpha-farnesene; CXENHBSYCFFKJS-GZCJILEISA-N; (3E,6E)- .alpha.-Farnesene; (3E,6E)-.ALPHA.-FARNESENE; alpha-Farnesene (natural); .alpha.-Farnesene, (E,E)-; .alpha.-Farnesene isomer; (E,E)-.alpha.-Farnesene; trans-.alpha.-Farnesene; trans,trans-α-Farnesene; (3E,6E)-alpha-Farnesene; .alpha.-trans-Farnesene; .ALPHA.-FARNESENE [MI]; farnesene (e,e-alpha-); (E,E)-alpha-farnesene; .alpha.-E,E-Farnesene; trans-alpha-farnesene; (E)-alpha-Farnesene; (3E,6E)-Α-farnesene; (3E,6E)-a-Farnesene; Sesquicitronellene; .alpha.-Farnesene; (E,E)-α-Farnesene; trans-α-Farnesene; alpha.-Farnesene; UNII-7E1785CZ0H; Alpha-Farnesene; trans-Farnesene; (E,E)-Farnesene; (E/Z)-Farnesene; I+/--farnesene; ??-Farnesene; Tox21_303626; α-Farnesene; a-farnesene; 7E1785CZ0H; FARNESENE-; Farnesene; (E,E)- -farnesene; α-Farnesene; alpha-Farnesene; alpha-Farnesene



数据库引用编号

27 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(0)

代谢反应

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(1)

PharmGKB(0)

114 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 12 ACLY, APRT, CAT, COASY, FDPS, FPR2, GPD1, GPI, IPP, PIN1, PIN4, TYR
Peripheral membrane protein 1 CYP1B1
Endoplasmic reticulum membrane 3 ACAT1, CYP1B1, HMGCR
Nucleus 2 PIN1, PIN4
cytosol 7 ACLY, APRT, CAT, FDPS, GPD1, GPI, PIN1
nucleoplasm 5 ACLY, APRT, FDPS, PIN1, PIN4
Cell membrane 2 FPR2, TNF
Multi-pass membrane protein 3 ACAT1, FPR2, HMGCR
cell surface 1 TNF
glutamatergic synapse 1 PIN1
Golgi apparatus 1 ATRN
neuronal cell body 1 TNF
Cytoplasm, cytosol 1 ACLY
Lysosome 1 TYR
plasma membrane 3 ATRN, FPR2, TNF
Membrane 8 ACAT1, ACLY, CAT, CYP1B1, FDPS, FPR2, GPI, HMGCR
extracellular exosome 8 ACAT1, ACLY, APRT, ATRN, CAT, COASY, GPD1, GPI
endoplasmic reticulum 3 ACAT1, GPX6, HMGCR
extracellular space 4 ATRN, GPI, IL6, TNF
perinuclear region of cytoplasm 1 TYR
mitochondrion 4 ACAT1, CAT, COASY, CYP1B1
protein-containing complex 1 CAT
intracellular membrane-bounded organelle 3 CAT, CYP1B1, TYR
Microsome membrane 1 CYP1B1
Single-pass type I membrane protein 2 ATRN, TYR
Secreted 4 GPI, GPX5, GPX6, IL6
extracellular region 8 ACLY, APRT, CAT, GPI, GPX5, GPX6, IL6, TNF
mitochondrial outer membrane 1 COASY
[Isoform 2]: Secreted 1 ATRN
Mitochondrion matrix 1 COASY
mitochondrial matrix 5 ACAT1, CAT, COASY, FDPS, PIN4
ciliary membrane 1 GPI
external side of plasma membrane 1 TNF
actin cytoskeleton 1 IPP
nucleolus 1 PIN4
Melanosome membrane 1 TYR
midbody 1 PIN1
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Membrane raft 1 TNF
focal adhesion 1 CAT
spindle 1 PIN4
Peroxisome 2 CAT, FDPS
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 2 CAT, HMGCR
nuclear speck 1 PIN1
ciliary basal body 1 PIN1
phagocytic cup 1 TNF
Chromosome 1 PIN4
[Isoform 3]: Secreted 1 ATRN
specific granule membrane 1 FPR2
tertiary granule membrane 1 FPR2
Melanosome 1 TYR
Nucleus speckle 1 PIN1
Peroxisome membrane 1 HMGCR
ficolin-1-rich granule lumen 3 ACLY, CAT, GPI
secretory granule lumen 3 APRT, CAT, GPI
endoplasmic reticulum lumen 2 GPX6, IL6
azurophil granule lumen 1 ACLY
ficolin-1-rich granule membrane 1 FPR2
[Isoform 1]: Cell membrane 1 ATRN
postsynaptic cytosol 1 PIN1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
interleukin-6 receptor complex 1 IL6
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
preribosome 1 PIN4


文献列表

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  • Dalila Touhami, Adedayo O Mofikoya, Robbie D Girling, Ben Langford, Pawel K Misztal, Christian Pfrang. Atmospheric Degradation of Ecologically Important Biogenic Volatiles: Investigating the Ozonolysis of (E)-β-Ocimene, Isomers of α and β-Farnesene, α-Terpinene and 6-Methyl-5-Hepten-2-One, and Their Gas-Phase Products. Journal of chemical ecology. 2024 Jan; ?(?):. doi: 10.1007/s10886-023-01467-6. [PMID: 38195852]
  • Xiaoyue Lun, Xiuxiu Xu, Yu Zhang, Ruirui Zhang, Yan Cao, Xiangzhi Zhang, Meina Jin, Zhengqun Zhang, Yunhe Zhao. An Antennae-Enriched Odorant-Binding Protein EonuOBP43 Mediate the Behavioral Response of the Tea Green Leafhopper, Empoasca onukii Matsuda to the Host and Nonhost Volatiles. Journal of agricultural and food chemistry. 2023 Dec; 71(50):20000-20010. doi: 10.1021/acs.jafc.3c07144. [PMID: 38059819]
  • Jossiê Zamperetti Donadel, Fabio Rodrigo Thewes, Luana Ferreira Dos Santos, Erani Eliseu Schultz, Magno Roberto Pasquetti Berghetti, Vagner Ludwig, Juliana Mesadri, Bruna Klein, Flavio Roberto Thewes, Suele Fernanda Prediger Schmidt, Vanderlei Both, Auri Brackmann, Daniel Alexandre Neuwald, Roger Wagner. Superficial scald development in 'Granny Smith' and 'Nicoter' apples: The role of key volatile compounds when fruit are stored under dynamic controlled atmosphere. Food research international (Ottawa, Ont.). 2023 Nov; 173(Pt 2):113396. doi: 10.1016/j.foodres.2023.113396. [PMID: 37803734]
  • Xinhua Zhang, Xiaohong Chen, Jaime A Teixeira da Silva, Ting Zhang, Yuping Xiong, Yuan Li, Yunfei Yuan, Xiaoping Pan, Guohua Ma. Characterization of sandalwood (E,E)-α-farnesene synthase whose overexpression enhances cold tolerance through jasmonic acid biosynthesis and signaling in Arabidopsis. Planta. 2023 Jul; 258(3):54. doi: 10.1007/s00425-023-04212-1. [PMID: 37515637]
  • Adam Yasgar, Danielle Bougie, Richard T Eastman, Ruili Huang, Misha Itkin, Jennifer Kouznetsova, Caitlin Lynch, Crystal McKnight, Mitch Miller, Deborah K Ngan, Tyler Peryea, Pranav Shah, Paul Shinn, Menghang Xia, Xin Xu, Alexey V Zakharov, Anton Simeonov. Quantitative Bioactivity Signatures of Dietary Supplements and Natural Products. ACS pharmacology & translational science. 2023 May; 6(5):683-701. doi: 10.1021/acsptsci.2c00194. [PMID: 37200814]
  • Liliane Sena Pinheiro, Valter Viana Andrade-Neto, Marcio Mantuano-Barradas, Elisa Cavalcante Pereira, Rodrigo Cesar Fernandes Barbosa, Marcia Cristina Campos de Oliveira, Rubem Figueiredo Sadok Menna-Barreto, Edézio Ferreira Cunha-Júnior, Eduardo Caio Torres-Santos. Biological effects of trans, trans-farnesol in Leishmania amazonensis. Frontiers in cellular and infection microbiology. 2023; 13(?):1221246. doi: 10.3389/fcimb.2023.1221246. [PMID: 38035328]
  • Shuhua Wu, Yuhua Yang, Jiaming Chen, Jianlong Li, Guotai Jian, Jie Yang, Kaiquan Mao, Lanting Zeng, Dachuan Gu. Histone deacetylase CsHDA6 mediates the regulated formation of the anti-insect metabolite α-farnesene in tea (Camellia sinensis). Plant science : an international journal of experimental plant biology. 2023 Jan; 326(?):111501. doi: 10.1016/j.plantsci.2022.111501. [PMID: 36257410]
  • Jingang He, Yunxiao Feng, Yudou Cheng, Thirupathi Karuppanapandian, Jinxiao Wang, Junfeng Guan. Changes in α-Farnesene and Phenolic Metabolism and the Expression of Associated Genes during the Development of Superficial Scald in Two Distinct Pear Cultivars. International journal of molecular sciences. 2022 Oct; 23(20):. doi: 10.3390/ijms232012088. [PMID: 36292939]
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  • Leo Lebanov, Brett Paull. Comparison of chemometric assisted targeted and untargeted approaches for the prediction of radical scavenging activity of ylang-ylang essential oils. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2022 Feb; 1191(?):123093. doi: 10.1016/j.jchromb.2021.123093. [PMID: 35065387]
  • Leo Lebanov, Shing Chung Lam, Laura Tedone, Tomislav Sostaric, Jason A Smith, Alireza Ghiasvand, Brett Paull. Radical scavenging activity and metabolomic profiling study of ylang-ylang essential oils based on high-performance thin-layer chromatography and multivariate statistical analysis. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2021 Aug; 1179(?):122861. doi: 10.1016/j.jchromb.2021.122861. [PMID: 34339956]
  • Christelle Lemaitre-Guillier, Christelle Dufresne, Agnès Chartier, Stéphanie Cluzet, Josep Valls, Lucile Jacquens, Antonin Douillet, Nicolas Aveline, Marielle Adrian, Xavier Daire. VOCs Are Relevant Biomarkers of Elicitor-Induced Defences in Grapevine. Molecules (Basel, Switzerland). 2021 Jul; 26(14):. doi: 10.3390/molecules26144258. [PMID: 34299533]
  • Junhua Wang, Wei Jiang, Chaojuan Liang, Linghuan Zhu, Youran Li, Qin Mo, Sha Xu, Alex Chu, Liang Zhang, Zhongyang Ding, Guiyang Shi. Overproduction of α-Farnesene in Saccharomyces cerevisiae by Farnesene Synthase Screening and Metabolic Engineering. Journal of agricultural and food chemistry. 2021 Mar; 69(10):3103-3113. doi: 10.1021/acs.jafc.1c00008. [PMID: 33683134]
  • Heng Liu, Shaohua Liu, Bingyang Du, Kuntian Dong, Yong Wang, Yuanhu Zhang. Aloe vera gel coating aggravates superficial scald incidence in 'Starking' apples during low-temperature storage. Food chemistry. 2021 Mar; 339(?):128151. doi: 10.1016/j.foodchem.2020.128151. [PMID: 33152896]
  • Guanhua Liu, Mei Yang, Jianyu Fu. Identification and characterization of two sesquiterpene synthase genes involved in volatile-mediated defense in tea plant (Camellia sinensis). Plant physiology and biochemistry : PPB. 2020 Oct; 155(?):650-657. doi: 10.1016/j.plaphy.2020.08.004. [PMID: 32858427]
  • Jieyang Jin, Shangrui Zhang, Mingyue Zhao, Tingting Jing, Na Zhang, Jingming Wang, Bin Wu, Chuankui Song. Scenarios of Genes-to-Terpenoids Network Led to the Identification of a Novel α/β-Farnesene/β-Ocimene Synthase in Camellia sinensis. International journal of molecular sciences. 2020 Jan; 21(2):. doi: 10.3390/ijms21020655. [PMID: 31963919]
  • Edwige J F Souleyre, Joanna K Bowen, Adam J Matich, Sumathi Tomes, Xiuyin Chen, Martin B Hunt, Mindy Y Wang, Nadeesha R Ileperuma, Kate Richards, Daryl D Rowan, David Chagné, Ross G Atkinson. Genetic control of α-farnesene production in apple fruit and its role in fungal pathogenesis. The Plant journal : for cell and molecular biology. 2019 12; 100(6):1148-1162. doi: 10.1111/tpj.14504. [PMID: 31436867]
  • Xuewen Wang, Lanting Zeng, Yinyin Liao, Jianlong Li, Jinchi Tang, Ziyin Yang. Formation of α-Farnesene in Tea (Camellia sinensis) Leaves Induced by Herbivore-Derived Wounding and Its Effect on Neighboring Tea Plants. International journal of molecular sciences. 2019 Aug; 20(17):. doi: 10.3390/ijms20174151. [PMID: 31450700]
  • Chia-Ming Liu, Shigeru Matsuyama, Yooichi Kainoh. Synergistic Effects of Volatiles from Host-Infested Plants on Host-Searching Behavior in the Parasitoid Wasp Lytopylus rufipes (Hymenoptera: Braconidae). Journal of chemical ecology. 2019 Aug; 45(8):684-692. doi: 10.1007/s10886-019-01088-y. [PMID: 31289990]
  • Bastien Durenne, Alodie Blondel, Philippe Druart, Marie-Laure Fauconnier. Epoxiconazole exposure affects terpenoid profiles of oilseed rape plantlets based on a targeted metabolomic approach. Environmental science and pollution research international. 2019 Jun; 26(17):17362-17372. doi: 10.1007/s11356-019-05110-4. [PMID: 31012076]
  • Wirginia Kukula-Koch, Wojciech Koch, Lidia Czernicka, Kazimierz Głowniak, Yoshinori Asakawa, Akemi Umeyama, Zbigniew Marzec, Takashi Kuzuhara. MAO-A Inhibitory Potential of Terpene Constituents from Ginger Rhizomes-A Bioactivity Guided Fractionation. Molecules (Basel, Switzerland). 2018 May; 23(6):. doi: 10.3390/molecules23061301. [PMID: 29844252]
  • Nitirat Chimnoi, Nanthawan Reuk-Ngam, Piyachat Chuysinuan, Panita Khlaychan, Nisachon Khunnawutmanotham, Daranee Chokchaichamnankit, Wassapol Thamniyom, Srikanjana Klayraung, Chulabhorn Mahidol, Supanna Techasakul. Characterization of essential oil from Ocimum gratissimum leaves: Antibacterial and mode of action against selected gastroenteritis pathogens. Microbial pathogenesis. 2018 May; 118(?):290-300. doi: 10.1016/j.micpath.2018.03.041. [PMID: 29578062]
  • Lanting Zeng, Yinyin Liao, Jianlong Li, Ying Zhou, Jinchi Tang, Fang Dong, Ziyin Yang. α-Farnesene and ocimene induce metabolite changes by volatile signaling in neighboring tea (Camellia sinensis) plants. Plant science : an international journal of experimental plant biology. 2017 Nov; 264(?):29-36. doi: 10.1016/j.plantsci.2017.08.005. [PMID: 28969800]
  • Ying Yu, Shiheng Lyu, Dan Chen, Yi Lin, Jianjun Chen, Guixin Chen, Naixing Ye. Volatiles Emitted at Different Flowering Stages of Jasminum sambac and Expression of Genes Related to α-Farnesene Biosynthesis. Molecules (Basel, Switzerland). 2017 Mar; 22(4):. doi: 10.3390/molecules22040546. [PMID: 28353656]
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  • Nicola Busatto, Brian Farneti, Alice Tadiello, Urska Vrhovsek, Luca Cappellin, Franco Biasioli, Riccardo Velasco, Guglielmo Costa, Fabrizio Costa. Target metabolite and gene transcription profiling during the development of superficial scald in apple (Malus x domestica Borkh). BMC plant biology. 2014 Jul; 14(?):193. doi: 10.1186/s12870-014-0193-7. [PMID: 25038781]
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  • Shi-Jing Liu, Nai-Yong Liu, Peng He, Zhao-Qun Li, Shuang-Lin Dong, Lan-Fang Mu. Molecular characterization, expression patterns, and ligand-binding properties of two odorant-binding protein genes from Orthaga achatina (Butler) (Lepidoptera: Pyralidae). Archives of insect biochemistry and physiology. 2012 Aug; 80(3):123-39. doi: 10.1002/arch.21036. [PMID: 22648659]
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