(-)-3-Isothujone (BioDeep_00000000664)

 

Secondary id: BioDeep_00000014736, BioDeep_00000036398, BioDeep_00000265584, BioDeep_00000279233

human metabolite PANOMIX_OTCML-2023 Endogenous Cytotoxicity


代谢物信息卡片


Bicyclo(3.1.0)hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1-alpha,4-alpha,5-alpha)-(+-)-

化学式: C10H16O (152.1201)
中文名称: (-)-α-侧柏酮, (-)-α-丁香, α-侧柏酮
谱图信息: 最多检出来源 Homo sapiens(plant) 21.49%

分子结构信息

SMILES: CC(C)[C@@]12CC(=O)[C@@H](C)[C@@H]1C2
InChI: InChI=1S/C10H16O/c1-6(2)10-4-8(10)7(3)9(11)5-10/h6-8H,4-5H2,1-3H3

描述信息

(-)-3-Isothujone is found in alcoholic beverages. Ingredient of absinthe. Presence in food and beverages regulated by legislation.Thujone is a ketone and a monoterpene that occurs naturally in two diastereomeric forms: (-)-alpha-thujone and (+)-beta-thujone. It has a menthol odor. In addition to (-)-alpha-thujone and (+)-beta-thujone, there are their enantiomeric forms, (+)-alpha-thujone and (-)-beta-thujone. (Wikipedia
(-)-alpha-thujone is the (1S,4R,5R)-stereoisomer of alpha-thujone. It is an enantiomer of a (+)-alpha-thujone.
alpha-Thujone is a natural product found in Xylopia sericea, Rhododendron mucronulatum, and other organisms with data available.
See also: Artemisia absinthium whole (part of).
A thujane monoterpenoid that is thujane substituted by an oxo group at position 3.
Ingredient of absinthe. Presence in food and beverages regulated by legislation
α-Thujone is a monoterpene isolated from Thuja occidentalis essential oil with potent anti-tumor activities. α-Thujone is a reversible modulator of the GABA type A receptor and the IC50 for α-Thujone is 21 μM in suppressing the GABA-induced currents. α-Thujone induces ROS accumulation-dependent cytotoxicity, also induces cell apoptosis and autophagy. α-Thujone has antinociceptive, insecticidal, and anthelmintic activity, and easily penetrates the blood-brain barrier[1][2][3].
α-Thujone is a monoterpene isolated from Thuja occidentalis essential oil with potent anti-tumor activities. α-Thujone is a reversible modulator of the GABA type A receptor and the IC50 for α-Thujone is 21 μM in suppressing the GABA-induced currents. α-Thujone induces ROS accumulation-dependent cytotoxicity, also induces cell apoptosis and autophagy. α-Thujone has antinociceptive, insecticidal, and anthelmintic activity, and easily penetrates the blood-brain barrier[1][2][3].
α-Thujone is a monoterpene isolated from Thuja occidentalis essential oil with potent anti-tumor activities. α-Thujone is a reversible modulator of the GABA type A receptor and the IC50 for α-Thujone is 21 μM in suppressing the GABA-induced currents. α-Thujone induces ROS accumulation-dependent cytotoxicity, also induces cell apoptosis and autophagy. α-Thujone has antinociceptive, insecticidal, and anthelmintic activity, and easily penetrates the blood-brain barrier[1][2][3].

同义名列表

68 个代谢物同义名

Bicyclo(3.1.0)hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1-alpha,4-alpha,5-alpha)-(+-)-; (1S-(1alpha,4alpha,5alpha))-4-methyl-1-(1-methylethyl)bicyclo(3.1.0)hexan-3-one; [1S-(1alpha,4alpha,5alpha)]-4-methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one; (-)-alpha-Thujone, (1S,4R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one; [1S-(1Α,4α,5α)]-4-methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one; [1S-(1a,4a,5a)]-4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one; Bicyclo[3.1.0]hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1S,4R,5R)-; Bicyclo(3.1.0)hexan-3-one, 4-methyl-1-(1-methylethyl)-, (1S,4R,5R)-; BICYCLO(3.1.0)HEXAN-3-ONE, 4-METHYL-1-(1-METHYLETHYL)-, (1S,5R)-; (1S,4R,5R)-4-Methyl-1-(1-methylethyl)bicyclo[3.1.0]hexan-3-one; (1S,4R,5R)-4-methyl-1-(propan-2-yl)bicyclo[3.1.0]hexan-3-one; (1S,4R,5R)-4-methyl-1-(propan-2-yl)bicyclo(3.1.0)hexan-3-one; (1S,4R,5R)-4-methyl-1-propan-2-ylbicyclo[3.1.0]hexan-3-one; (1R,2R,5S)-5-isopropyl-2-methyl-bicyclo[3.1.0]hexan-3-one; (1S,4R,5R)-1-isopropyl-4-methylbicyclo(3.1.0)hexan-3-one; (1S,4R,5R)-1-isopropyl-4-methylbicyclo[3.1.0]hexan-3-one; (1S,4R)-1-Isopropyl-4-methylbicyclo[3.1.0]hexan-3-one; beta-thujone, (1S-(1alpha,4alpha,5alpha))-isomer; beta-thujone, 1S-(1alpha,4beta,5alpha)-isomer; beta-thujone, (1alpha,4alpha,5alpha)-isomer; (-)-alpha-Thujone, >=96.0\\% (GC); (-)-Thujone ((-)-alpha-Thujone); 3-Thujanone, (1S,4R,5R)-(-)-; (1S,4R,5R)-(-)-3-thujanone; (1S,4R,5R)- 3-THUJANONE; (1S,4R,5R)-thujan-3-one; (-)-alpha,beta-Thujone; .ALPHA.-THUJONE [MI]; racemic 3-Isothujone; (-)- alpha -Thujone; alpha, beta-thujone; 3-Thujanone, (+-)-; THUJONE, .ALPHA.-; (-)-alpha-thujone; 3-Thujanone, (-)-; (-)-trans-Thujone; alpha-(-)-Thujone; (-)-3-Isothujone; L-alpha-Thujone; UNII-R0SQ9G0DU5; .alpha.-Thujone; (-)-3-thujanone; (+-)-Isothujone; (-)-Isothujone; a-(-)-THUJONE; (-)-α-Thujone; alpha-thujone; (-)-a-Thujone; beta-thujone; ALFA-THUJONE; 3-isothujone; Tox21_200868; cis-thujone; (-)-thujone; 3-thujanone; (+)-thujone; 86HK1QRJ4K; R0SQ9G0DU5; ??-Thujone; dl-Thujone; α-Thujone; a-Thujone; l-Thujone; Absinthol; Thujone; Thujon; Thujone; Thujone



数据库引用编号

28 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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100 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 BECN1, CASP1, CASP3, CAT, CYP2A6, CYP2B6, CYP3A4, DCTN4, PHB1, PRKAA2, SOD1, VEGFA
Golgi apparatus, trans-Golgi network membrane 1 BECN1
Peripheral membrane protein 4 ACHE, BECN1, CYP1B1, CYP2B6
Endosome membrane 2 BECN1, CLCN5
Endoplasmic reticulum membrane 5 BECN1, CYP1B1, CYP2A6, CYP2B6, CYP3A4
Mitochondrion membrane 1 BECN1
Cytoplasmic vesicle, autophagosome 1 BECN1
Nucleus 8 ACHE, BECN1, CASP3, DCTN4, PHB1, PRKAA2, SOD1, VEGFA
autophagosome 1 BECN1
cytosol 9 BECN1, CASP1, CASP3, CAT, CLCN5, DCTN4, PRKAA2, SLC2A4, SOD1
dendrite 2 BECN1, PRKAA2
mitochondrial membrane 1 BECN1
nuclear body 1 BECN1
phagocytic vesicle 1 BECN1
phosphatidylinositol 3-kinase complex, class III 1 BECN1
trans-Golgi network 2 BECN1, SLC2A4
centrosome 1 DCTN4
nucleoplasm 4 CASP3, PHB1, PRKAA2, SOD1
Cell membrane 6 ACHE, CASP1, CLCN5, PHB1, SLC2A4, TNF
Multi-pass membrane protein 2 CLCN5, SLC2A4
Golgi apparatus membrane 1 CLCN5
Synapse 1 ACHE
cell cortex 1 DCTN4
cell surface 4 ACHE, PHB1, TNF, VEGFA
glutamatergic synapse 1 CASP3
Golgi apparatus 4 ACHE, CLCN5, PRKAA2, VEGFA
Golgi membrane 2 CLCN5, INS
lysosomal membrane 1 CLCN5
mitochondrial inner membrane 1 PHB1
neuromuscular junction 1 ACHE
neuronal cell body 4 CASP3, PRKAA2, SOD1, TNF
sarcolemma 1 SLC2A4
synaptic vesicle 1 CLCN5
Presynapse 1 SLC2A4
endosome 1 BECN1
plasma membrane 6 ACHE, CASP1, CLCN5, PHB1, SLC2A4, TNF
Membrane 10 ACHE, CAT, CLCN5, CYP1B1, CYP2A6, CYP3A4, PHB1, PRKAA2, SLC2A4, VEGFA
axon 1 PRKAA2
extracellular exosome 4 CAT, PHB1, SLC2A4, SOD1
endoplasmic reticulum 2 BECN1, VEGFA
extracellular space 7 ACHE, IL2, IL6, INS, SOD1, TNF, VEGFA
perinuclear region of cytoplasm 2 ACHE, SLC2A4
adherens junction 1 VEGFA
mitochondrion 4 CAT, CYP1B1, PHB1, SOD1
protein-containing complex 3 CASP1, CAT, SOD1
intracellular membrane-bounded organelle 5 CAT, CYP1B1, CYP2A6, CYP2B6, CYP3A4
Microsome membrane 3 CYP1B1, CYP2B6, CYP3A4
postsynaptic density 1 CASP3
Secreted 5 ACHE, IL2, IL6, INS, VEGFA
extracellular region 8 ACHE, CAT, IL2, IL6, INS, SOD1, TNF, VEGFA
mitochondrial matrix 2 CAT, SOD1
Extracellular side 1 ACHE
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 DCTN4
external side of plasma membrane 2 SLC2A4, TNF
Secreted, extracellular space, extracellular matrix 1 VEGFA
multivesicular body 1 SLC2A4
T-tubule 1 SLC2A4
cytoplasmic vesicle 1 SOD1
nucleolus 1 CASP1
axon cytoplasm 1 SOD1
Early endosome 2 CLCN5, PHB1
apical part of cell 1 CLCN5
clathrin-coated pit 1 SLC2A4
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Cytoplasm, perinuclear region 1 SLC2A4
Mitochondrion inner membrane 1 PHB1
Membrane raft 2 SLC2A4, TNF
Cytoplasm, cytoskeleton 1 DCTN4
focal adhesion 2 CAT, DCTN4
microtubule 1 CASP1
extracellular matrix 1 VEGFA
Peroxisome 2 CAT, SOD1
basement membrane 1 ACHE
sarcoplasmic reticulum 1 SLC2A4
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
mitochondrial intermembrane space 1 SOD1
secretory granule 1 VEGFA
nuclear speck 1 PRKAA2
NLRP3 inflammasome complex 1 CASP1
dendrite cytoplasm 1 SOD1
Cytoplasm, myofibril, sarcomere 1 DCTN4
sarcomere 1 DCTN4
phagocytic cup 1 TNF
spindle pole 1 DCTN4
Cytoplasm, cell cortex 1 DCTN4
Lipid-anchor, GPI-anchor 1 ACHE
Endomembrane system 1 SLC2A4
endosome lumen 1 INS
phagophore assembly site 1 BECN1
phosphatidylinositol 3-kinase complex, class III, type I 1 BECN1
phosphatidylinositol 3-kinase complex, class III, type II 1 BECN1
Cytoplasmic vesicle membrane 1 SLC2A4
cytoplasmic stress granule 1 PRKAA2
side of membrane 1 ACHE
stress fiber 1 DCTN4
clathrin-coated vesicle 1 SLC2A4
trans-Golgi network transport vesicle 1 SLC2A4
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 IL6, INS
platelet alpha granule lumen 1 VEGFA
dynactin complex 1 DCTN4
kinetochore 1 DCTN4
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
cytoplasmic dynein complex 1 DCTN4
AIM2 inflammasome complex 1 CASP1
vesicle membrane 1 SLC2A4
Cytoplasm, cytoskeleton, stress fiber 1 DCTN4
cytoplasmic microtubule 1 CYP2A6
synaptic cleft 1 ACHE
death-inducing signaling complex 1 CASP3
canonical inflammasome complex 1 CASP1
nucleotide-activated protein kinase complex 1 PRKAA2
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
interleukin-6 receptor complex 1 IL6
insulin-responsive compartment 1 SLC2A4
[N-VEGF]: Cytoplasm 1 VEGFA
[VEGFA]: Secreted 1 VEGFA
[Isoform L-VEGF189]: Endoplasmic reticulum 1 VEGFA
[Isoform VEGF121]: Secreted 1 VEGFA
[Isoform VEGF165]: Secreted 1 VEGFA
VEGF-A complex 1 VEGFA
[Isoform H]: Cell membrane 1 ACHE
cytoplasmic side of mitochondrial outer membrane 1 BECN1
IPAF inflammasome complex 1 CASP1
NLRP1 inflammasome complex 1 CASP1
protease inhibitor complex 1 CASP1
mitochondrial prohibitin complex 1 PHB1
[Beclin-1-C 35 kDa]: Mitochondrion 1 BECN1
[Beclin-1-C 37 kDa]: Mitochondrion 1 BECN1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • R Sasidharan, L Brokate, E J Eilers, C Müller. Chemodiversity in flowers of Tanacetum vulgare has consequences on a florivorous beetle. Plant biology (Stuttgart, Germany). 2023 Dec; 25(7):1071-1082. doi: 10.1111/plb.13576. [PMID: 37703504]
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  • Hua Shao, Yunxia Hu, Caixia Han, Caixia Wei, Shixing Zhou, Chenpeng Zhang, Chi Zhang. Chemical Composition and Phytotoxic Activity of Seriphidium terrae-albae (Krasch.) Poljakov (Compositae) Essential Oil. Chemistry & biodiversity. 2018 Nov; 15(11):e1800348. doi: 10.1002/cbdv.201800348. [PMID: 30168654]
  • Chiara Di Lorenzo, Francesco Ferretti, Enzo Moro, Alessandro Ceschi, Francesca Colombo, Gianfranco Frigerio, Saskia Lüde, Patrizia Restani. Identification and Quantification of Thujone in a Case of Poisoning Due to Repeated Ingestion of an Infusion of Artemisia Vulgaris L. Journal of food science. 2018 Aug; 83(8):2257-2264. doi: 10.1111/1750-3841.14273. [PMID: 30044501]
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  • Alessandra Manzo, Loana Musso, Sara Panseri, Marcello Iriti, Sabrina Dallavalle, Enrico Catalano, Giorgio Scarì, Annamaria Giorgi. Screening of the chemical composition and bioactivity of Waldheimia glabra (Decne.) Regel essential oil. Journal of the science of food and agriculture. 2016 Jul; 96(9):3195-201. doi: 10.1002/jsfa.7499. [PMID: 26467601]
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