fenchone (BioDeep_00000007642)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(1R,4S)-(+)-fenchone;(1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one

化学式: C10H16O (152.1201)
中文名称: 葑酮, （-）-芬可酮, 芬胆碱
谱图信息: 最多检出来源 Viridiplantae(plant) 27.45%

分子结构信息

SMILES: C12(C(=O)C(C)(C)C(CC1)C2)C
InChI: InChI=1S/C10H16O/c1-9(2)7-4-5-10(3,6-7)8(9)11/h7H,4-6H2,1-3H3

描述信息

A carbobicyclic compound that is fenchane in which the hydrogens at position 2 are replaced by an oxo group. It is a component of essential oil from fennel (Foeniculum vulgare).
Fenchone is a natural organic compound classified as a monoterpene and a ketone. It is a colorless oily liquid. It has a structure and an odor similar to camphor. Fenchone is a constituent of absinthe and the essential oil of fennel. Fenchone is used as a flavor in foods and in perfumery. Only 2 stereoisomers are possible: D-fenchone (enantiomer 1S,4R is dextrogyre (+)) and L-fenchone (enantiomer 1R,4S is levogyre (-)). Due to the small size of the cycle, the 2 other diastereoisomers (1S4S and 1R4R) are not possible. [Wikipedia]. Fenchone is found in many foods, some of which are ceylon cinnamon, sweet basil, saffron, and dill.
(-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1].
(-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1].
(-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1].
(-)-Fenchone, a bicyclic monoterpene, is widely distributed in plants and found in essential oils from Foeniculum vulgare. (-)-Fenchone is oxidized to 6-endo-hydroxyfenchone, 6-exo-hydroxyfenchone and 10-hydroxyfenchone derivatives by CYP2A6 and CYP2B6 in human liver microsomes with CYP2A6 playing a more important role than CYP2B6[1].

同义名列表

9 个代谢物同义名

fenchone; (1R,4S)-(+)-fenchone;(1R,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-one; (1R,4S)-fenchan-2-one; (1R,4S)-fenchone; (.+/-.)-Fenchone; (-)-Fenchone; Fenchone; (-)-Fenchone; Fenchone



数据库引用编号

23 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)

231 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 8 CNR2, ELANE, FGF18, HPGDS, MARVELD1, PTGS2, TJP1, TYR
Peripheral membrane protein 3 ACHE, PTGS2, TJP1
Endoplasmic reticulum membrane 1 PTGS2
Nucleus 4 ACHE, MARVELD1, SOX9, TJP1
cytosol 3 ELANE, HPGDS, TJP1
dendrite 1 CNR2
phagocytic vesicle 1 ELANE
nucleoplasm 2 HPGDS, SOX9
Cell membrane 7 ACHE, CLDN1, KIT, MARVELD1, PTGER4, TJP1, TNF
Cytoplasmic side 1 TJP1
Multi-pass membrane protein 3 CLDN1, MARVELD1, PTGER4
Synapse 2 ACHE, TAC1
cell junction 1 TJP1
cell surface 3 ACHE, ELANE, TNF
Golgi apparatus 1 ACHE
lysosomal membrane 1 GAA
neuromuscular junction 1 ACHE
neuronal cell body 2 TAC1, TNF
Lysosome 2 GAA, TYR
acrosomal vesicle 1 KIT
plasma membrane 9 ACHE, CLDN1, CNR2, GAA, KIT, MARVELD1, PTGER4, TJP1, TNF
Membrane 6 ACHE, CLDN1, GAA, KIT, MARVELD1, PTGER4
apical plasma membrane 2 CLDN1, TJP1
axon 1 TAC1
basolateral plasma membrane 2 CLDN1, TJP1
caveola 1 PTGS2
extracellular exosome 2 ELANE, GAA
Lysosome membrane 1 GAA
endoplasmic reticulum 2 CNR2, PTGS2
extracellular space 8 ACHE, CRP, ELANE, FGF18, IL17A, KIT, TAC1, TNF
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 2 ACHE, TYR
Cell junction, tight junction 2 CLDN1, TJP1
adherens junction 1 TJP1
apicolateral plasma membrane 1 TJP1
bicellular tight junction 2 CLDN1, TJP1
gap junction 1 TJP1
intercalated disc 1 TJP1
intercellular canaliculus 1 TJP1
mitochondrion 1 TJP1
protein-containing complex 4 CLDN1, PTGS2, SOX9, TJP1
intracellular membrane-bounded organelle 3 GAA, HPGDS, TYR
Microsome membrane 1 PTGS2
Single-pass type I membrane protein 2 KIT, TYR
Secreted 6 ACHE, CRP, FGF18, GAA, IL17A, VIP
extracellular region 10 ACHE, CRP, ELANE, FGF18, GAA, IL17A, MLN, TAC1, TNF, VIP
cytoplasmic side of plasma membrane 1 KIT
Single-pass membrane protein 1 MLN
Extracellular side 1 ACHE
transcription regulator complex 1 SOX9
external side of plasma membrane 3 IL17A, KIT, TNF
perikaryon 1 CNR2
nucleolus 1 FGF18
Melanosome membrane 1 TYR
apical part of cell 1 TJP1
cell-cell junction 1 KIT
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
postsynaptic membrane 1 CNR2
Membrane raft 1 TNF
Cytoplasm, cytoskeleton 1 MARVELD1
basement membrane 1 ACHE
collagen-containing extracellular matrix 1 ELANE
secretory granule 1 ELANE
lateral plasma membrane 1 CLDN1
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 1 KIT
neuron projection 2 PTGS2, VIP
chromatin 1 SOX9
cell projection 1 TJP1
phagocytic cup 1 TNF
cytoskeleton 1 MARVELD1
Cell projection, podosome 1 TJP1
podosome 1 TJP1
Basolateral cell membrane 1 CLDN1
Lipid-anchor, GPI-anchor 1 ACHE
fibrillar center 1 KIT
Cell projection, dendrite 1 CNR2
tertiary granule membrane 1 GAA
Melanosome 1 TYR
side of membrane 1 ACHE
[Isoform 3]: Cytoplasm 1 KIT
endoplasmic reticulum lumen 1 PTGS2
transcription repressor complex 1 ELANE
specific granule lumen 1 ELANE
azurophil granule membrane 1 GAA
tight junction 2 CLDN1, TJP1
azurophil granule lumen 1 ELANE
Sarcoplasmic reticulum membrane 1 MLN
extrinsic component of cytoplasmic side of plasma membrane 1 CNR2
synaptic cleft 1 ACHE
ficolin-1-rich granule membrane 1 GAA
apical junction complex 1 TJP1
Cytoplasmic vesicle, phagosome 1 ELANE
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
autolysosome lumen 1 GAA
[Isoform H]: Cell membrane 1 ACHE
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Li Cui, Yongzhi Hua, Shuting Zou, Chao Gu, Hui Li. Combination of fenchone and sodium hyaluronate ameliorated constipation-predominant irritable bowel syndrome and underlying mechanisms. Chemical biology & drug design. 2024 Jan; 103(1):e14397. doi: 10.1111/cbdd.14397. [PMID: 38030381]
  • Li Cui, Bin Zhang, Shuting Zou, Jing Liu, Pingrong Wang, Hui Li, Zhenhai Zhang. Fenchone Ameliorates ConstipationPredominant Irritable Bowel Syndrome via Modulation of SCF/c-Kit Pathway and Gut Microbiota. Journal of microbiology and biotechnology. 2023 Oct; 34(2):1-12. doi: 10.4014/jmb.2308.08011. [PMID: 38073315]
  • Shoaib Nawaz, Hafiz Muhammad Irfan, Alamgeer, Laiba Arshad, Shah Jahan. Attenuation of CFA-induced chronic inflammation by a bicyclic monoterpene fenchone targeting inducible nitric oxide, prostaglandins, C-reactive protein and urea. Inflammopharmacology. 2023 Sep; ?(?):. doi: 10.1007/s10787-023-01333-7. [PMID: 37689616]
  • Farzad Rasouli, Yousef Nasiri, Mohammad Bagher Hassanpouraghdam, Mohammad Asadi, Taher Qaderi, Amini Trifa, Maciej Strzemski, Sławomir Dresler, Małgorzata Szczepanek. Seaweed extract and arbuscular mycorrhiza co-application affect the growth responses and essential oil composition of Foeniculum vulgare L. Scientific reports. 2023 07; 13(1):11902. doi: 10.1038/s41598-023-39194-3. [PMID: 37488427]
  • Elaheh Sadat Hosseini, Mohammad Mahdi Majidi, Mohammad Hossein Ehtemam, N Hughes. Characterization of fennel germplasm for physiological persistence and drought recovery: Association with biochemical properties. Plant physiology and biochemistry : PPB. 2023 Jan; 194(?):499-512. doi: 10.1016/j.plaphy.2022.11.037. [PMID: 36516537]
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  • Michelle Liz de Souza Pessoa, Leiliane Macena Oliveira Silva, Maria Elaine Cristina Araruna, Catarina Alves de Lima Serafim, Edvaldo Balbino Alves Júnior, Alessa Oliveira Silva, Matheus Marley Bezerra Pessoa, Hermes Diniz Neto, Edeltrudes de Oliveira Lima, Leônia Maria Batista. Antifungal activity and antidiarrheal activity via antimotility mechanisms of (-)-fenchone in experimental models. World journal of gastroenterology. 2020 Nov; 26(43):6795-6809. doi: 10.3748/wjg.v26.i43.6795. [PMID: 33268962]
  • J S Rosa, L Oliveira, R M O F Sousa, C B Escobar, M Fernandes-Ferreira. Bioactivity of some Apiaceae essential oils and their constituents against Sitophilus zeamais (Coleoptera: Curculionidae). Bulletin of entomological research. 2020 Jun; 110(3):406-416. doi: 10.1017/s0007485319000774. [PMID: 31813390]
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