Verbinone (BioDeep_00000000972)

 

Secondary id: BioDeep_00000398726

human metabolite PANOMIX_OTCML-2023 blood metabolite


代谢物信息卡片


Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1R-cis)-

化学式: C10H14O (150.1045)
中文名称: 马鞭草烯酮, 马苄烯酮, 马鞭草酮, (-)-马鞭烯酮
谱图信息: 最多检出来源 Homo sapiens(blood) 88.33%

分子结构信息

SMILES: CC1=CC(=O)C2CC1C2(C)C
InChI: InChI=1S/C10H14O/c1-6-4-9(11)8-5-7(6)10(8,2)3/h4,7-8H,5H2,1-3H3

描述信息

Verbenone, also known as verbenone, (1r)-isomer, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Verbenone is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Verbenone is a camphor, celery, and menthol tasting compound and can be found in a number of food items such as spearmint, cabbage, white cabbage, and rosemary, which makes verbenone a potential biomarker for the consumption of these food products. Verbenone is a natural organic compound classified as a terpene that is found naturally in a variety of plants. The chemical has a pleasant characteristic odor. Besides being a natural constituent of plants, it and its analogs are insect pheromones. In particular, verbenone when formulated in a long-lasting matrix has an important role in the control of bark beetles such as the mountain pine beetle and the Southern pine bark beetle .
4,6,6-trimethylbicyclo[3.1.1]hept-3-en-2-one is a carbobicyclic compound that is bicyclo[3.1.1]heptane which is substituted by an oxo group at position 2 and by methyl groups at positions 4, 6 and 6, and which contains a double bond between positions 3 and 4. It is a carbobicyclic compound, a cyclic ketone and an enone.
Verbenone is a natural product found in Eucalyptus fasciculosa, Eucalyptus intertexta, and other organisms with data available.
Verbenone ((-)-Verbenone) is a natural terpene in leaves of the tree, Verbena officinalis[1]. Verbenone has anti-aggregation pheromone and interrupts the attraction of bark beetles to their aggregation pheromones[2].
Verbenone ((-)-Verbenone) is a natural terpene in leaves of the tree, Verbena officinalis[1]. Verbenone has anti-aggregation pheromone and interrupts the attraction of bark beetles to their aggregation pheromones[2].

同义名列表

35 个代谢物同义名

Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1R-cis)-; Bicyclo[3.1.1]hept-3-en-2-one,4,6,6-trimethyl-, (1R,5R)-; 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one, (1R-cis)-; 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one, (1S,5S)-; 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one, (1R,5R)-; Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1R)-; Bicyclo[3.1.1]hept-3-en-2-one, 4,6,6-trimethyl-, (1S)-; (1R-cis)-4,6,6-Trimethylbicyclo(3.1.1)hept-3-ene-2-one; (-)-4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one; 4,6,6-Trimethylbicyclo[3.1.1]hept-3-en-2-one; 2,6,6-trimethylbicyclo[3.1.1]hept-2-en-4-one; 2-Pinen-4-one, (1S,5S)-(-)-; (1s)-(-)-pin-2-en-4-one; verbenone, (1R)-isomer; verbenone, (1S)-isomer; verbenone, (+-)-isomer; (-)-cis-verbenone; (-)-2-Pinen-4-one; (S)-(-)-Verbenone; Verbenone (D,L-); Verbenone, (L)-; Verbenone, (d)-; VERBENONE,(DL); 2-Pinen-4-one; (S)-verbenone; dl-Verbenone; S-Verbenone; d-Verbenone; Verbinone; Verbenone; (-)-Verbenone; Verbenone; D-Verbenone; Verbenone; (-)-Verbenone



数据库引用编号

20 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)

27 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 7 BCL2, CCNB1, CDK1, MDM2, MME, PMP2, SGCB
Peripheral membrane protein 1 CYP1B1
Endoplasmic reticulum membrane 5 BCL2, BSG, CDK1, CYP1B1, ELOVL2
Nucleus 8 BCL2, CCNB1, CDK1, MDM2, PMP2, PPARGC1A, TCEA1, TFAM
cytosol 7 BCL2, CCNB1, CDK1, MDM2, PMP2, PPARGC1A, TFAM
dendrite 2 ELOVL2, MME
trans-Golgi network 1 MME
centrosome 2 CCNB1, CDK1
nucleoplasm 5 CCNB1, CDK1, MDM2, PPARGC1A, TCEA1
Cell membrane 3 BSG, MME, TNF
Multi-pass membrane protein 1 ELOVL2
Synapse 1 MME
cell surface 2 MME, TNF
glutamatergic synapse 1 MDM2
Golgi apparatus 1 ATRN
Golgi membrane 2 BSG, INS
neuronal cell body 3 ELOVL2, MME, TNF
sarcolemma 2 BSG, SGCB
synaptic vesicle 1 MME
Presynapse 1 MME
endosome 1 BSG
plasma membrane 8 ATRN, BSG, F2, KNG1, MDM2, MME, SGCB, TNF
Membrane 7 BCL2, BSG, CCNB1, CDK1, CYP1B1, ELOVL2, MME
axon 1 MME
basolateral plasma membrane 1 BSG
brush border 1 MME
extracellular exosome 7 ATRN, BSG, CDK1, F2, KNG1, MME, PMP2
endoplasmic reticulum 2 BCL2, ELOVL2
extracellular space 6 ATRN, CRP, F2, INS, KNG1, TNF
mitochondrion 5 BCL2, BSG, CDK1, CYP1B1, TFAM
protein-containing complex 3 BCL2, MDM2, TFAM
intracellular membrane-bounded organelle 2 BSG, CYP1B1
Microsome membrane 1 CYP1B1
postsynaptic density 1 MDM2
Single-pass type I membrane protein 2 ATRN, BSG
Secreted 3 CRP, F2, INS
extracellular region 5 CRP, F2, INS, KNG1, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
[Isoform 2]: Secreted 1 ATRN
mitochondrial matrix 3 CCNB1, CDK1, TFAM
photoreceptor inner segment 1 BSG
photoreceptor outer segment 1 BSG
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 CDK1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 TNF
cytoplasmic vesicle 1 MME
nucleolus 2 MDM2, TCEA1
midbody 1 CDK1
Early endosome 1 MME
recycling endosome 1 TNF
Single-pass type II membrane protein 3 MME, SGCB, TNF
Cell membrane, sarcolemma 1 SGCB
Membrane raft 2 MME, TNF
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 SGCB
focal adhesion 2 BSG, MME
mitochondrial nucleoid 1 TFAM
Nucleus, PML body 1 PPARGC1A
PML body 1 PPARGC1A
collagen-containing extracellular matrix 2 F2, KNG1
lateral plasma membrane 1 BSG
chromatin 1 PPARGC1A
phagocytic cup 1 TNF
mitotic spindle 1 CDK1
cytoskeleton 1 SGCB
Cell projection, cilium, photoreceptor outer segment 1 BSG
Secreted, extracellular space 1 KNG1
Nucleus, nucleolus 1 MDM2
spindle pole 1 CCNB1
chromosome, telomeric region 1 CDK1
blood microparticle 2 F2, KNG1
Basolateral cell membrane 1 BSG
[Isoform 2]: Cell membrane 1 BSG
[Isoform 3]: Secreted 1 ATRN
endosome lumen 1 INS
Nucleus, nucleoplasm 1 MDM2
Cell projection, dendrite 1 ELOVL2
Melanosome 1 BSG
myelin sheath 2 BCL2, PMP2
secretory granule lumen 1 INS
secretory granule membrane 1 MME
Golgi lumen 2 F2, INS
endoplasmic reticulum lumen 3 F2, INS, KNG1
transcription repressor complex 1 MDM2
transcription factor TFIID complex 1 TCEA1
platelet alpha granule lumen 1 KNG1
endocytic vesicle membrane 1 MDM2
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
outer kinetochore 1 CCNB1
[Isoform 1]: Nucleus 1 PPARGC1A
spindle microtubule 1 CDK1
[Isoform 1]: Cell membrane 2 ATRN, BSG
dystrophin-associated glycoprotein complex 1 SGCB
sarcoglycan complex 1 SGCB
acrosomal membrane 1 BSG
[Isoform 3]: Cell membrane 1 BSG
cyclin-dependent protein kinase holoenzyme complex 1 CDK1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
cyclin A1-CDK1 complex 1 CDK1
cyclin A2-CDK1 complex 1 CDK1
cyclin B1-CDK1 complex 2 CCNB1, CDK1
neuron projection terminus 1 MME
BAD-BCL-2 complex 1 BCL2
[Isoform 4]: Cell membrane 1 BSG
Mitochondrion matrix, mitochondrion nucleoid 1 TFAM
dendritic tree 1 ELOVL2
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF
[Isoform B4]: Nucleus 1 PPARGC1A
[Isoform B4-8a]: Cytoplasm 1 PPARGC1A
[Isoform B5]: Nucleus 1 PPARGC1A
[Isoform 9]: Nucleus 1 PPARGC1A


文献列表

  • Ahlem Bekhechi, Charaf Eddine Watheq Malti, Brahim Babali, Miloud Bouafia, Chahrazed Bekhechi, Joseph Casanova, Mathieu Paoli, Félix Tomi. Chemical Variability and Anti-Inflammatory Activity of Rosmarinus officinalis L. Leaf Essential Oil from Algerian Sahara. Chemistry & biodiversity. 2024 Apr; 21(4):e202302077. doi: 10.1002/cbdv.202302077. [PMID: 38388803]
  • Tobias Frühbrodt, Baoguo Du, Horst Delb, Tim Burzlaff, Jürgen Kreuzwieser, Peter H W Biedermann. Know When You Are Too Many: Density-Dependent Release of Pheromones During Host Colonisation by the European Spruce Bark Beetle, Ips typographus (L.). Journal of chemical ecology. 2023 Oct; ?(?):. doi: 10.1007/s10886-023-01453-y. [PMID: 37789096]
  • Antonio Raffo, Irene Baiamonte, Laura De Benedetti, Elisabetta Lupotto, Ilaria Marchioni, Nicoletta Nardo, Claudio Cervelli. Exploring volatile aroma and non-volatile bioactive compounds diversity in wild populations of rosemary (Salvia rosmarinus Schleid.). Food chemistry. 2023 Mar; 404(Pt A):134532. doi: 10.1016/j.foodchem.2022.134532. [PMID: 36242966]
  • Monica L Gaylord, Jackson P Audley, Joel D McMillin, Christopher J Fettig. Acetophenone and Green Leaf Volatiles Do Not Enhance the Efficacy of Verbenone for Inhibiting Attraction of Ips pini (Coleoptera: Curculionidae) to Pheromone-baited Traps in Northern Arizona. Journal of economic entomology. 2023 Feb; ?(?):. doi: 10.1093/jee/toad016. [PMID: 36744905]
  • Jaime-Andrés Becerra, Juan-Miguel González, Aída-Luz Villa. Comparison by Life-Cycle Assessment of Alternative Processes for Carvone and Verbenone Production. Molecules (Basel, Switzerland). 2022 Aug; 27(17):. doi: 10.3390/molecules27175479. [PMID: 36080248]
  • Qingjie Cao, Tuuli-Marjaana Koski, Huiping Li, Chi Zhang, Jianghua Sun. The effect of inactivation of aldehyde dehydrogenase on pheromone production by a gut bacterium of an invasive bark beetle, Dendroctonus valens. Insect science. 2022 Aug; ?(?):. doi: 10.1111/1744-7917.13101. [PMID: 36003004]
  • Hansel E González-Velasco, María S Pérez-Gutiérrez, Ángel J Alonso-Castro, Juan R Zapata-Morales, Perla Del C Niño-Moreno, Nimsi Campos-Xolalpa, Marco M González-Chávez. Anti-Inflammatory and Antinociceptive Activities of the Essential Oil of Tagetes parryi A. Gray (Asteraceae) and Verbenone. Molecules (Basel, Switzerland). 2022 Apr; 27(9):. doi: 10.3390/molecules27092612. [PMID: 35565963]
  • Jackson P Audley, Richard M Bostock, Steven J Seybold. Trap Assays of the Walnut Twig Beetle, Pityophthorus juglandis Blackman (Coleoptera: Curculionidae: Scolytinae), Reveal an Effective Semiochemical Repellent Combination. Journal of chemical ecology. 2020 Dec; 46(11-12):1047-1058. doi: 10.1007/s10886-020-01228-9. [PMID: 33106973]
  • Xin-Sheng Liu, Bo Gao, Xin-Lu Li, Wan-Nan Li, Zi-An Qiao, Lu Han. Chemical Composition and Antimicrobial and Antioxidant Activities of Essential Oil of Sunflower (Helianthus annuus L.) Receptacle. Molecules (Basel, Switzerland). 2020 Nov; 25(22):. doi: 10.3390/molecules25225244. [PMID: 33187052]
  • Monique J Rivera, Xavier Martini, Derrick Conover, Agenor Mafra-Neto, Daniel Carrillo, Lukasz L Stelinski. Evaluation of semiochemical based push-pull strategy for population suppression of ambrosia beetle vectors of laurel wilt disease in avocado. Scientific reports. 2020 02; 10(1):2670. doi: 10.1038/s41598-020-59569-0. [PMID: 32060382]
  • María Pardo-Muras, Carolina G Puig, Nuria Pedrol. Cytisus scoparius and Ulex europaeus Produce Volatile Organic Compounds with Powerful Synergistic Herbicidal Effects. Molecules (Basel, Switzerland). 2019 Dec; 24(24):. doi: 10.3390/molecules24244539. [PMID: 31835831]
  • C X Wu, F Liu, S F Zhang, X B Kong, Z Zhang. Semiochemical Regulation of the Intraspecific and Interspecific Behavior of Tomicus yunnanensis and Tomicus minor during the Shoot-Feeding Phase. Journal of chemical ecology. 2019 Mar; 45(3):227-240. doi: 10.1007/s10886-019-01048-6. [PMID: 30796677]
  • Elena Drosopoulou, Dimitris Vlastos, Ioanna Efthimiou, Paraskevi Kyrizaki, Sofia Tsamadou, Maria Anagnostopoulou, Danai Kofidou, Maxim Gavriilidis, Despoina Mademtzoglou, Penelope Mavragani-Tsipidou. In vitro and in vivo evaluation of the genotoxic and antigenotoxic potential of the major Chios mastic water constituents. Scientific reports. 2018 08; 8(1):12200. doi: 10.1038/s41598-018-29810-y. [PMID: 30111795]
  • John A Byers, Yonatan Maoz, David Wakarchuk, Daniela Fefer, Anat Levi Zada. Inhibitory Effects of Semiochemicals on the Attraction of an Ambrosia Beetle Euwallacea nr. fornicatus to Quercivorol. Journal of chemical ecology. 2018 Jun; 44(6):565-575. doi: 10.1007/s10886-018-0959-8. [PMID: 29663165]
  • Qiong Hu, Gui-Shan Lin, Wen-Gui Duan, Min Huang, Fu-Hou Lei. Synthesis and Biological Activity of Novel (Z)- and (E)-Verbenone Oxime Esters. Molecules (Basel, Switzerland). 2017 Oct; 22(10):. doi: 10.3390/molecules22101678. [PMID: 29023419]
  • Letian Xu, Min Lu, Dandan Xu, Li Chen, Jianghua Sun. Sexual variation of bacterial microbiota of Dendroctonus valens guts and frass in relation to verbenone production. Journal of insect physiology. 2016 12; 95(?):110-117. doi: 10.1016/j.jinsphys.2016.09.014. [PMID: 27677696]
  • Kenichi Tomi, Makiko Kitao, Norihiro Konishi, Hiroshi Murakami, Yasuki Matsumura, Takahiro Hayashi. Enantioselective GC-MS analysis of volatile components from rosemary (Rosmarinus officinalis L.) essential oils and hydrosols. Bioscience, biotechnology, and biochemistry. 2016 May; 80(5):840-7. doi: 10.1080/09168451.2016.1146066. [PMID: 26923429]
  • Haobin Hu, Xudong Zheng, Huaisheng Hu, Ruirui Wang, Yun Wu. Study on gas chromatography-mass spectrometry fingerprint of Acanthopanax brachypus. Journal of chromatographic science. 2014 Sep; 52(8):759-65. doi: 10.1093/chromsci/bmt137. [PMID: 24076562]
  • Nancy E Gillette, Sandra J Kegley, Sheryl L Costello, Sylvia R Mori, Jeffrey N Webster, Constance J Mehmel, David L Wood. Efficacy of verbenone and green leaf volatiles for protecting whitebark and limber pines from attack by mountain pine beetle (Coleoptera: Curculionidae: Scolytinae). Environmental entomology. 2014 Aug; 43(4):1019-26. doi: 10.1603/en12330. [PMID: 25003785]
  • M Hassine, A Zardi-Berguaoui, M Znati, G Flamini, H Ben Jannet, M A Hamza. Chemical composition, antibacterial and cytotoxic activities of the essential oil from the flowers of Tunisian Convolvulus althaeoides L. Natural product research. 2014; 28(11):769-75. doi: 10.1080/14786419.2013.879476. [PMID: 24498906]
  • Ji-Yeon Yang, Hoi-Seon Lee. Verbenone structural analogues isolated from Artemesia aucheri as natural acaricides against Dermatophagoides spp. and Tyrophagus putrescentiae. Journal of agricultural and food chemistry. 2013 Dec; 61(50):12292-6. doi: 10.1021/jf404849t. [PMID: 24295367]
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  • Daniella K S Lima, Laudir J Ballico, Fernanda Rocha Lapa, Hilda P Gonçalves, Lauro Mera de Souza, Marcello Iacomini, Maria Fernanda de Paula Werner, Cristiane Hatsuko Baggio, Isabela Tiemy Pereira, Luisa Mota da Silva, Valdir A Facundo, Adair Roberto Soares Santos. Evaluation of the antinociceptive, anti-inflammatory and gastric antiulcer activities of the essential oil from Piper aleyreanum C.DC in rodents. Journal of ethnopharmacology. 2012 Jun; 142(1):274-82. doi: 10.1016/j.jep.2012.05.016. [PMID: 22588049]
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  • Rafal Szmigielski, Marek Cieslak, Krzysztof J Rudziński, Barbara Maciejewska. Identification of volatiles from Pinus silvestris attractive for Monochamus galloprovincialis using a SPME-GC/MS platform. Environmental science and pollution research international. 2011 Aug; 19(7):2860-9. doi: 10.1007/s11356-012-0792-5. [PMID: 22322293]
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  • Angelike Triantafyllou, Alfiya Bikineyeva, Anna Dikalova, Rafal Nazarewicz, Stamatios Lerakis, Sergey Dikalov. Anti-inflammatory activity of Chios mastic gum is associated with inhibition of TNF-alpha induced oxidative stress. Nutrition journal. 2011 Jun; 10(?):64. doi: 10.1186/1475-2891-10-64. [PMID: 21645369]
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  • Qing-He Zhang, Fredrik Schlyter. Inhibition of predator attraction to kairomones by non-host plant volatiles for herbivores: a bypass-trophic signal. PloS one. 2010 Jun; 5(6):e11063. doi: 10.1371/journal.pone.0011063. [PMID: 20548795]
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