Menthone (BioDeep_00000279402)

 

Secondary id: BioDeep_00000000875, BioDeep_00000014720, BioDeep_00000016656, BioDeep_00000396929, BioDeep_00000859893, BioDeep_00001868466

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2R,5S)-rel-

化学式: C10H18O (154.1358)
中文名称: 5-甲基-2-(1-甲乙基)环已硐, 异薄荷酮, 顺-5-甲基-2-(1-甲基乙基)环己酮, 胡薄荷酮, 薄荷酮
谱图信息: 最多检出来源 Homo sapiens(plant) 16.16%

分子结构信息

SMILES: CC(C)C1CCC(C)CC1=O
InChI: InChI=1S/C10H18O/c1-7(2)9-5-4-8(3)6-10(9)11/h7-9H,4-6H2,1-3H3

描述信息

P-menthan-3-one is a p-menthane monoterpenoid that is p-menthane substituted by an oxo group at position 3. It has a role as a plant metabolite and a volatile oil component.
p-Menthan-3-one is a natural product found in Citrus hystrix, Mentha aquatica, and other organisms with data available.
The trans-stereoisomer of p-menthan-3-one.
Flavouring compound [Flavornet]
(-)-Menthone is a monoterpene component of the essential oil of maturing peppermint. (+)-Neomenthyl-β-d-glucoside is a metabolite of (-)-Menthone[1].Mortality of two biological forms of Anopheles stephensi(larvae) exposed to about 45 ppm (-)-Menthone is 27.67\\\\\\% and 94.92\\\\\\%. [2]
(-)-Menthone is a monoterpene component of the essential oil of maturing peppermint. (+)-Neomenthyl-β-d-glucoside is a metabolite of (-)-Menthone[1].Mortality of two biological forms of Anopheles stephensi(larvae) exposed to about 45 ppm (-)-Menthone is 27.67\\\\\% and 94.92\\\\\%. [2]
(-)-Menthone is a monoterpene component of the essential oil of maturing peppermint. (+)-Neomenthyl-β-d-glucoside is a metabolite of (-)-Menthone[1].Mortality of two biological forms of Anopheles stephensi(larvae) exposed to about 45 ppm (-)-Menthone is 27.67\\\\% and 94.92\\\\%. [2]
(-)-Menthone is a monoterpene component of the essential oil of maturing peppermint. (+)-Neomenthyl-β-d-glucoside is a metabolite of (-)-Menthone[1].Mortality of two biological forms of Anopheles stephensi(larvae) exposed to about 45 ppm (-)-Menthone is 27.67\\\% and 94.92\\\%. [2]
Menthone, a monoterpene extracted from plants and Mentha oil with strong antioxidant properties. Menthone is a main volatile component of the essential oil, and has anti-Inflammatory properties in Schistosoma mansoni Infection[1][2].
Menthone, a monoterpene extracted from plants and Mentha oil with strong antioxidant properties. Menthone is a main volatile component of the essential oil, and has anti-Inflammatory properties in Schistosoma mansoni Infection[1][2].

同义名列表

43 个代谢物同义名

Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2R,5S)-rel-; Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2R-cis)-; Cyclohexanone, 5-methyl-2-(1-methylethyl)-, (2S-cis)-; 1-(4-CHLOROBENZYL)PIPERIDIN-4-AMINETRIFLUOROACETATE; (2R,5S)-rel-5-methyl-2-(1-methylethyl)cyclohexanone; Cyclohexanone,5-methyl-2-(1-methylethyl)-,(2S,5R)-; rel-(2R,5S)-5-methyl-2-(propan-2-yl)cyclohexanone; (2S-cis)-2-(Isopropyl)-5-methylcyclohexan-1-one; rel-(2R,5S)-2-isopropyl-5-methylcyclohexanone; trans-5-methyl-2-(1-methylethyl)cyclohexanone; Cyclohexanone, 5-methyl-2-(1-methylethyl)-; 2-(1-methylethyl)-5-methyl-cyclohexanone; 5-methyl-2-(propan-2-yl)cyclohexan-1-one; 5-Methyl-2-(1-methylethyl)cyclohexanone; 5-methyl-2-propan-2-ylcyclohexan-1-one; 5-methyl-2-(propan-2-yl)cyclohexanone; 5-Methyl-2-(isopropyl)cyclohexanone; 5-Methyl-2-(isopropylcyclo)hexanone; 2-Isopropyl-5-methyl-cyclohexanone; 2-Isopropyl-5-methylcyclohexanone; p-Menthan-3-one, (1R,4R)-(+)-; p-Menthan-3-one, (1S,4S)-(-)-; Menthone, analytical standard; rel-(1R,4S)-p-menthan-3-one; p-Menthan-3-one; (±)-Isomenthone; 3-p-menthanone; Isomenthone Dl; ISO-MENTHONE; p-Menthanone; DL-Menthone; iso-Mentone; p-Menthone; a menthone; Menthone; l-MENTHONE; (-)-Menthone; (-)-Menthone; (-)-Isomenthone; p-Menthan-3-one; (+)-Isomenthone; p-Menthan-3-one; Menthone



数据库引用编号

39 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(1)

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)

229 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 CASP1, CCR3, MME, PTGS1, PTGS2, TYK2, TYR
Peripheral membrane protein 4 ACHE, HSD17B6, PTGS1, PTGS2
Endoplasmic reticulum membrane 2 PTGS1, PTGS2
Nucleus 2 ACHE, TYK2
cytosol 2 CASP1, TYK2
dendrite 1 MME
trans-Golgi network 1 MME
Cell membrane 5 ACHE, CASP1, CCR3, MME, TNF
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 1 CCR3
Synapse 2 ACHE, MME
cell surface 3 ACHE, MME, TNF
Golgi apparatus 2 ACHE, PTGS1
lysosomal membrane 1 GAA
neuromuscular junction 1 ACHE
neuronal cell body 2 MME, TNF
synaptic vesicle 1 MME
Lysosome 3 GAA, SHKBP1, TYR
Presynapse 1 MME
plasma membrane 10 ACHE, BCHE, CASP1, CCR3, CXCR1, GAA, IFNLR1, MME, TNF, TYK2
Membrane 6 ACHE, CCR3, GAA, IFNLR1, MME, TYK2
axon 1 MME
brush border 1 MME
caveola 1 PTGS2
extracellular exosome 4 GAA, MME, PTGS1, TYK2
Lysosome membrane 1 GAA
Lumenal side 1 HSD17B6
endoplasmic reticulum 2 HSD17B6, PTGS2
extracellular space 8 ACHE, BCHE, CCL11, IL10, IL2, IL4, IL5, TNF
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 2 ACHE, TYR
protein-containing complex 2 CASP1, PTGS2
intracellular membrane-bounded organelle 4 GAA, HSD17B6, PTGS1, TYR
Microsome membrane 3 HSD17B6, PTGS1, PTGS2
Single-pass type I membrane protein 2 IFNLR1, TYR
Secreted 8 ACHE, BCHE, CCL11, GAA, IL10, IL2, IL4, IL5
extracellular region 9 ACHE, BCHE, CCL11, GAA, IL10, IL2, IL4, IL5, TNF
cytoplasmic side of plasma membrane 1 TYK2
Extracellular side 1 ACHE
photoreceptor outer segment 1 PTGS1
external side of plasma membrane 3 CCR3, CXCR1, TNF
cytoplasmic vesicle 1 MME
nucleolus 1 CASP1
Melanosome membrane 1 TYR
Early endosome 1 MME
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
Single-pass type II membrane protein 2 MME, TNF
Membrane raft 2 MME, TNF
focal adhesion 1 MME
microtubule 1 CASP1
basement membrane 1 ACHE
NLRP3 inflammasome complex 1 CASP1
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
neuron projection 2 PTGS1, PTGS2
phagocytic cup 1 TNF
cytoskeleton 1 TYK2
blood microparticle 1 BCHE
Lipid-anchor, GPI-anchor 1 ACHE
Endomembrane system 1 PTGS1
tertiary granule membrane 1 GAA
Melanosome 1 TYR
side of membrane 1 ACHE
secretory granule membrane 2 CXCR1, MME
endoplasmic reticulum lumen 2 BCHE, PTGS2
azurophil granule membrane 1 GAA
nuclear envelope lumen 1 BCHE
AIM2 inflammasome complex 1 CASP1
extrinsic component of cytoplasmic side of plasma membrane 1 TYK2
synaptic cleft 1 ACHE
ficolin-1-rich granule membrane 1 GAA
canonical inflammasome complex 1 CASP1
extrinsic component of plasma membrane 1 TYK2
interleukin-12 receptor complex 1 TYK2
interleukin-23 receptor complex 1 TYK2
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
neuron projection terminus 1 MME
autolysosome lumen 1 GAA
[Isoform H]: Cell membrane 1 ACHE
IPAF inflammasome complex 1 CASP1
NLRP1 inflammasome complex 1 CASP1
protease inhibitor complex 1 CASP1
interleukin-28 receptor complex 1 IFNLR1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Xin An, Yangzhen Liao, Yifan Yu, Jiahe Fan, Jingqiong Wan, Yuan Wei, Zhen Ouyang. Effects of MhMYB1 and MhMYB2 transcription factors on the monoterpenoid biosynthesis pathway in l-menthol chemotype of Mentha haplocalyx Briq. Planta. 2024 May; 260(1):3. doi: 10.1007/s00425-024-04441-y. [PMID: 38767800]
  • Bartłomiej Piasecki, Izabela Korona-Głowniak, Anna Kiełtyka-Dadasiewicz, Agnieszka Ludwiczuk. Composition and Anti-Helicobacter pylori Properties of Essential Oils Obtained from Selected Mentha Cultivars. Molecules (Basel, Switzerland). 2023 Jul; 28(15):. doi: 10.3390/molecules28155690. [PMID: 37570659]
  • Paco Noriega, Lissette Calderón, Andrea Ojeda, Erika Paredes. Chemical Composition, Antimicrobial and Antioxidant Bioautography Activity of Essential Oil from Leaves of Amazon Plant Clinopodium brownei (Sw.). Molecules (Basel, Switzerland). 2023 Feb; 28(4):. doi: 10.3390/molecules28041741. [PMID: 36838728]
  • Wenming Zhao, Chengwei Yang, Ning Zhang, Yuanyuan Peng, Ying Ma, Keru Gu, Xia Liu, Xiaohui Liu, Xijian Liu, Yumin Liu, Songkai Li, Linjing Zhao. Menthone Exerts its Antimicrobial Activity Against Methicillin Resistant Staphylococcus aureus by Affecting Cell Membrane Properties and Lipid Profile. Drug design, development and therapy. 2023; 17(?):219-236. doi: 10.2147/dddt.s384716. [PMID: 36721663]
  • Hui Zhao, Shan Ren, Han Yang, Shun Tang, Chenyang Guo, Maolun Liu, Qiu Tao, Tianqi Ming, Haibo Xu. Peppermint essential oil: its phytochemistry, biological activity, pharmacological effect and application. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2022 Oct; 154(?):113559. doi: 10.1016/j.biopha.2022.113559. [PMID: 35994817]
  • Yi-Hsuan Su, Jin-Yuarn Lin. Menthone supplementation protects from allergic inflammation in the lungs of asthmatic mice. European journal of pharmacology. 2022 Sep; 931(?):175222. doi: 10.1016/j.ejphar.2022.175222. [PMID: 35988786]
  • Jiajia Zeng, Wenjuan Wang, Junjun Lin, Yuchi Zhang, Hao Li, Jiangang Liu, Chen Yan, Yanxiang Gu, Yun Wei. Purification of menthone and menthol from Mentha haplocalyx by suspension particle assisted solvent sublation, neuroprotective effect in vitro and molecular docking of menthol on amyloid-β. Journal of chromatography. A. 2022 Jul; 1674(?):463125. doi: 10.1016/j.chroma.2022.463125. [PMID: 35597196]
  • Xiangjie Chen, Qiuyu Wu, Zheng Gong, Tengfei Ren, Qian Du, Yukang Yuan, Yibo Zuo, Ying Miao, Jiuyi He, Caixia Qiao, Zhijin Zheng, Tingting Zhang, Lin Huang, Zhijun Xie, Jun Wang, Yueping Zhu, Chuanwu Zhu, Yang Xu, Depei Wu, Fangyuan Gong, Junping Cheng, Chengping Wen, Hui Zheng. A Natural Plant Ingredient, Menthone, Regulates T Cell Subtypes and Lowers Pro-inflammatory Cytokines of Rheumatoid Arthritis. Journal of natural products. 2022 04; 85(4):1109-1117. doi: 10.1021/acs.jnatprod.1c01231. [PMID: 35302365]
  • Mohammed Messaoudi, Abdelkrim Rebiai, Barbara Sawicka, Maria Atanassova, Hamza Ouakouak, Imane Larkem, Chukwuebuka Egbuna, Chinaza Godswill Awuchi, Sihem Boubekeur, Mohamed Amine Ferhat, Samir Begaa, Naima Benchikha. Effect of Extraction Methods on Polyphenols, Flavonoids, Mineral Elements, and Biological Activities of Essential Oil and Extracts of Mentha pulegium L. Molecules (Basel, Switzerland). 2021 Dec; 27(1):. doi: 10.3390/molecules27010011. [PMID: 35011242]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Daniela Grul'ová, Mária Pl'uchtová, Jozef Fejér, Laura De Martino, Lucia Caputo, Vincent Sedlák, Vincenzo De Feo. Influence of six essential oils on invasive Solidago canadensis L. seed germination. Natural product research. 2020 Nov; 34(22):3231-3233. doi: 10.1080/14786419.2018.1552694. [PMID: 30689411]
  • Sayed Amin Alavi, Ahmad Mohammadi Ghehsareh, Ali Soleymani, Ebrahim Panahpour, Morteza Mozafari. Pepermint (Mentha piperita L.) growth and biochemical properties affected by magnetized saline water. Ecotoxicology and environmental safety. 2020 Sep; 201(?):110775. doi: 10.1016/j.ecoenv.2020.110775. [PMID: 32535365]
  • Amanda Gisler, Jiayi Lan, Kapil Dev Singh, Jakob Usemann, Urs Frey, Renato Zenobi, Pablo Sinues. Real-time breath analysis of exhaled compounds upon peppermint oil ingestion by secondary electrospray ionization-high resolution mass spectrometry: technical aspects. Journal of breath research. 2020 07; 14(4):046001. doi: 10.1088/1752-7163/ab9f8b. [PMID: 32691749]
  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Yee Ching Ng, Ye Won Kim, Jeong-Su Lee, Sung Joon Lee, Moon Jung Song. Antiviral activity of Schizonepeta tenuifolia Briquet against noroviruses via induction of antiviral interferons. Journal of microbiology (Seoul, Korea). 2018 Sep; 56(9):683-689. doi: 10.1007/s12275-018-8228-7. [PMID: 30141161]
  • Mehdi Teymouri, Ardalan Alizadeh. Chemical composition and antimicrobial activity of the essential oil of Mentha mozaffarianii Jamzad growing wild and cultivated in Iran. Natural product research. 2018 Jun; 32(11):1320-1323. doi: 10.1080/14786419.2017.1342082. [PMID: 28658991]
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  • Abdelhakim Bouyahya, Abdeslam Et-Touys, Youssef Bakri, Ahmed Talbaui, Hajiba Fellah, Jamal Abrini, Nadia Dakka. Chemical composition of Mentha pulegium and Rosmarinus officinalis essential oils and their antileishmanial, antibacterial and antioxidant activities. Microbial pathogenesis. 2017 Oct; 111(?):41-49. doi: 10.1016/j.micpath.2017.08.015. [PMID: 28821401]
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  • Liam M Heaney, Dorota M Ruszkiewicz, Kayleigh L Arthur, Andria Hadjithekli, Clive Aldcroft, Martin R Lindley, Cl Paul Thomas, Matthew A Turner, James C Reynolds. Real-time monitoring of exhaled volatiles using atmospheric pressure chemical ionization on a compact mass spectrometer. Bioanalysis. 2016 Jul; 8(13):1325-36. doi: 10.4155/bio-2016-0045. [PMID: 27277875]
  • E Darvishi, D Kahrizi, S Bahraminejad, M Mansouri. In vitro induction of α-pinene, pulegone, menthol, menthone and limonene in cell suspension culture of pennyroyal (Mentha pulegium). Cellular and molecular biology (Noisy-le-Grand, France). 2016 Mar; 62(3):7-9. doi: . [PMID: 27064866]
  • Yi Lan, Jingyan Wang, Hui Li, Yewen Zhang, Yanyan Chen, Bochen Zhao, Qing Wu. Effect of menthone and related compounds on skin permeation of drugs with different lipophilicity and molecular organization of stratum corneum lipids. Pharmaceutical development and technology. 2016; 21(4):389-98. doi: 10.3109/10837450.2015.1011660. [PMID: 25684238]
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  • Daniela Grulova, Laura De Martino, Emilia Mancini, Ivan Salamon, Vincenzo De Feo. Seasonal variability of the main components in essential oil of Mentha × piperita L. Journal of the science of food and agriculture. 2015 Feb; 95(3):621-7. doi: 10.1002/jsfa.6802. [PMID: 24965379]
  • Guanying Hu, Xing Yuan, Sanyin Zhang, Ruru Wang, Miao Yang, Chunjie Wu, Zhigang Wu, Xiao Ke. Research on choleretic effect of menthol, menthone, pluegone, isomenthone, and limonene in DanShu capsule. International immunopharmacology. 2015 Feb; 24(2):191-197. doi: 10.1016/j.intimp.2014.12.001. [PMID: 25499726]
  • Franco Matías Escobar, María Carola Sabini, Laura Noelia Cariddi, Liliana Inés Sabini, Fernando Mañas, Andrea Cristofolini, Guillermo Bagnis, Mauro Nicolas Gallucci, Lilia Renée Cavaglieri. Safety assessment of essential oil from Minthostachys verticillata (Griseb.) Epling (peperina): 90-days oral subchronic toxicity study in rats. Regulatory toxicology and pharmacology : RTP. 2015 Feb; 71(1):1-7. doi: 10.1016/j.yrtph.2014.11.001. [PMID: 25445298]
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  • Mario Chessa, Angela Sias, Andrea Piana, Giuseppe Salvatore Mangano, Giacomo Luigi Petretto, Maria Dolores Masia, Bruno Tirillini, Giorgio Pintore. Chemical composition and antibacterial activity of the essential oil from Mentha requienii Bentham. Natural product research. 2013; 27(2):93-9. doi: 10.1080/14786419.2012.658798. [PMID: 22385272]
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  • Djamel Djenane, Mohammed Aïder, Javier Yangüela, Lamia Idir, Diego Gómez, Pedro Roncalés. Antioxidant and antibacterial effects of Lavandula and Mentha essential oils in minced beef inoculated with E. coli O157:H7 and S. aureus during storage at abuse refrigeration temperature. Meat science. 2012 Dec; 92(4):667-74. doi: 10.1016/j.meatsci.2012.06.019. [PMID: 22789458]
  • Diana Dobravalskytė, Petras Rimantas Venskutonis, Thierry Talou. Antioxidant properties and essential oil composition of Calamintha grandiflora L. Food chemistry. 2012 Dec; 135(3):1539-46. doi: 10.1016/j.foodchem.2012.05.094. [PMID: 22953891]
  • Eunsun Jung, Sangyo Byun, Seungbeom Kim, Moohan Kim, Deokhoon Park, Jongsung Lee. Isomenthone protects human dermal fibroblasts from TNF-α-induced death possibly by preventing activation of JNK and p38 MAPK. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2012 Oct; 50(10):3514-20. doi: 10.1016/j.fct.2012.07.002. [PMID: 22796318]
  • Franco Matías Escobar, Laura Noelia Cariddi, María Carola Sabini, Elina Reinoso, Sonia Beatriz Sutil, Cristina Vanesa Torres, Silvia Matilde Zanon, Liliana Inés Sabini. Lack of cytotoxic and genotoxic effects of Minthostachys verticillata essential oil: studies in vitro and in vivo. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2012 Sep; 50(9):3062-7. doi: 10.1016/j.fct.2012.06.018. [PMID: 22727859]
  • Emine Nur Herken, Ali Celik, Mustafa Aslan, Nilüfer Aydınlık. The constituents of essential oil: antimicrobial and antioxidant activity of Micromeria congesta Boiss. & Hausskn. ex Boiss. from East Anatolia. Journal of medicinal food. 2012 Sep; 15(9):835-9. doi: 10.1089/jmf.2011.0315. [PMID: 22871061]
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