(R)-Methysticin (BioDeep_00000000412)
Secondary id: BioDeep_00000406379, BioDeep_00000911024
human metabolite PANOMIX_OTCML-2023
代谢物信息卡片
化学式: C15H14O5 (274.0841)
中文名称: 麻醉椒苦素, 麻醉椒苫素, ( )-麻醉椒苦素
谱图信息:
最多检出来源 Chinese Herbal Medicine(otcml) 20.12%
分子结构信息
SMILES: COC1=CC(=O)OC(C1)C=CC2=CC3=C(C=C2)OCO3
InChI: InChI=1S/C15H14O5/c1-17-12-7-11(20-15(16)8-12)4-2-10-3-5-13-14(6-10)19-9-18-13/h2-6,8,11H,7,9H2,1H3/b4-2-
描述信息
Methysticin is a member of 2-pyranones and an aromatic ether.
Methysticin is a natural product found in Piper methysticum and Piper majusculum with data available.
See also: Piper methysticum root (part of).
(R)-Methysticin is found in beverages. (R)-Methysticin is found in kava (Piper methysticum). FDA advises against use of kava in food due to potential risk of severe liver damage (2002).
Found in kava (Piper methysticum). FDA advises against use of kava in food due to potential risk of severe liver damage (2002)
Methylsticin is a kavalactone isolated from the Piper methysticum . Methylsticin exhibit osteoclast formation inhibitory activity[1].
Methylsticin is a kavalactone isolated from the Piper methysticum . Methylsticin exhibit osteoclast formation inhibitory activity[1].
同义名列表
34 个代谢物同义名
5-Hydroxy-3-methoxy-7-(3,4-(methylenedioxy)phenyl)-2,6-heptadienoic acid gamma-lactone; 2H-Pyran-2-one,6-[(1E)-2-(1,3-benzodioxol-5-yl)ethenyl]-5,6-dihydro-4-methoxy-, (6R)-; 2H-Pyran-2-one, 6-(2-(1,3-benzodioxol-5-yl)ethenyl)-5,6-dihydro-4-methoxy-, (R-(E))-; (6R)-6-((1E)-2-(1,3-BENZODIOXOL-5-YL)ETHENYL)-5,6-DIHYDRO-4-METHOXY-2H-PYRAN-2-ONE; 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(3,4-(methylenedioxy)styryl)-, (R)- (VAN); (R-(E))-6-(2-(1,3-Benzodioxol-5-yl)ethenyl)-5,6-dihydro-4-methoxy-2H-pyran-2-one; (R,E)-6-(2-(benzo[d][1,3]dioxol-5-yl)vinyl)-4-methoxy-5,6-dihydro-2H-pyran-2-one; (6R)-6-[(E)-2-(1,3-benzodioxol-5-yl)vinyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one; 6-[(Z)-2-(2H-1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-5,6-dihydro-2H-pyran-2-one; (2R)-2-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-2,3-dihydropyran-6-one; 2H-Pyran-2-one,3-benzodioxol-5-yl)ethenyl]-5,6-dihydro-4-methoxy-, [R-(E)]-; 4-Methoxy-6-(beta-(3,4-methylenedioxyphenyl)vinyl)-5,6-dihydro-alpha-pyrone; 2H-Pyran-2-one, 5,6-dihydro-4-methoxy-6-(3,4-(methylenedioxy)styryl)-, (R)-; (2R)-2-[(E)-2-(1,3-benzodioxol-5-yl)vinyl]-4-methoxy-2,3-dihydropyran-6-one; 6-[(Z)-2-(2H-1,3-benzodioxol-5-yl)ethenyl]-4-methoxy-5,6-dihydropyran-2-one; 2H-Pyran-2-one,6-dihydro-4-methoxy-6-[3,4-(methylenedioxy)styryl]-, (R)-; 2H-Pyran-2-one,6-dihydro-4-methoxy-6-[3,4-(methylenedioxy)styryl]-, (+)-; (6R)-6-(2-Benzo[1,3]Dioxol-5-ylethenyl)-4-Methoxy-5,6-Dihydropyran-2-one; (R)-5,6-Dihydro-4-methoxy-6-(3,4-(methylenedioxy)styryl)-2H-pyran-2-one; 6-(3,4-METHYLENEDIOXYSTYRYL)-4-METHOXY-5,6-DIHYDRO-2H-PYRAN-2-ONE; 5-19-10-00456 (Beilstein Handbook Reference); Ethyl 2-(isobutoxycarbonylamino)acetate; R-(+)-Methysticin, analytical standard; methysticin, ((E)-(+-))-isomer; R-(+)-Methysticin; METHYSTICIN [MI]; (+)-Methysticin; (R)-Methysticin; Tox21_200901; Methylsticin; Methysticin; Kavatin; Kavahin; Methysticin
数据库引用编号
25 个数据库交叉引用编号
- ChEBI: CHEBI:174607
- ChEBI: CHEBI:6895
- KEGG: C09952
- PubChem: 90125683
- PubChem: 5281567
- PubChem: 229851
- HMDB: HMDB0033590
- Metlin: METLIN68039
- ChEMBL: CHEMBL579224
- Wikipedia: Methysticin
- MeSH: methysticin
- ChemIDplus: 0000495852
- KNApSAcK: C00003005
- foodb: FDB011667
- chemspider: 35013635
- chemspider: 4444889
- CAS: 20697-20-5
- CAS: 495-85-2
- medchemexpress: HY-N0922
- medchemexpress: HY-N2465
- PMhub: MS000001733
- PubChem: 12138
- 3DMET: B03407
- NIKKAJI: J6.085B
- KNApSAcK: 6895
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)
6 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。
文献列表
- 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] - Qiuying Zhang, Hui Liu, Dongmei Wu, Hongyan Yu, Kun Wang, Weijie Jiao, Xu Zhao. Methysticin Acts as a Mechanism-Based Inactivator of Cytochrome P450 2C9.
Chemical research in toxicology.
2022 06; 35(6):1117-1124. doi:
10.1021/acs.chemrestox.2c00098. [PMID: 35583123] - Philip W Melchert, Yuli Qian, Qingchen Zhang, Brandon O Klee, Chengguo Xing, John S Markowitz. In vitro inhibition of carboxylesterase 1 by Kava (Piper methysticum) Kavalactones.
Chemico-biological interactions.
2022 Apr; 357(?):109883. doi:
10.1016/j.cbi.2022.109883. [PMID: 35278473] - Adila Tuerxuntayi, Abudourusuli Tusun, Abulikemu Tajiguli. Rapid detection and structural characterization of methysticin metabolites generated from rat and human liver microsomes and hepatocytes using ultra-high-performance liquid chromatography coupled with high-resolution mass spectrometry.
Rapid communications in mass spectrometry : RCM.
2021 Dec; 35(24):e9208. doi:
10.1002/rcm.9208. [PMID: 34606659] - Antonio Celentano, Callisthenis Yiannis, Rita Paolini, Pangzhen Zhang, Camile S Farah, Nicola Cirillo, Tami Yap, Michael McCullough. Kava constituents exert selective anticancer effects in oral squamous cell carcinoma cells in vitro.
Scientific reports.
2020 09; 10(1):15904. doi:
10.1038/s41598-020-73058-4. [PMID: 32985597] - Callisthenis Yiannis, Kevin Huang, An Nhien Tran, Cathy Zeng, Emily Dao, Oliver Baselyous, Muaaz Adil Mithwani, Rita Paolini, Nicola Cirillo, Tami Yap, Michael McCullough, Antonio Celentano. Protective effect of kava constituents in an in vitro model of oral mucositis.
Journal of cancer research and clinical oncology.
2020 Jul; 146(7):1801-1811. doi:
10.1007/s00432-020-03253-3. [PMID: 32435894] - Jonna Berry, Ashley Gilbert, Justin Grodnitzky. Cases of Kava Impairment in Iowa Drivers.
Journal of forensic sciences.
2019 Nov; 64(6):1943-1949. doi:
10.1111/1556-4029.14130. [PMID: 31305953] - Yijin Tang, Christine Fields. A UHPLC-UV Method Development and Validation for Determining Kavalactones and Flavokavains in Piper methysticum (Kava).
Molecules (Basel, Switzerland).
2019 Mar; 24(7):. doi:
10.3390/molecules24071245. [PMID: 30934989] - Ying Liu, Jensen A Lund, Susan J Murch, Paula N Brown. Single-Lab Validation for Determination of Kavalactones and Flavokavains in Piper methysticum (Kava).
Planta medica.
2018 Nov; 84(16):1213-1218. doi:
10.1055/a-0637-2400. [PMID: 29940660] - Adele Murauer, Markus Ganzera. Quantitative Determination of Lactones in Piper methysticum (Kava-Kava) by Supercritical Fluid Chromatography.
Planta medica.
2017 Aug; 83(12-13):1053-1057. doi:
10.1055/s-0043-100632. [PMID: 28095587] - Atul Upadhyay, Emmy Tuenter, Rizwan Ahmad, Adnan Amin, Vasiliki Exarchou, Sandra Apers, Nina Hermans, Luc Pieters. Kavalactones, a novel class of protein glycation and lipid peroxidation inhibitors.
Planta medica.
2014 Aug; 80(12):1001-8. doi:
10.1055/s-0034-1382949. [PMID: 25098935] - Yan Li, Hu Mei, Qiangen Wu, Suhui Zhang, Jia-Long Fang, Leming Shi, Lei Guo. Methysticin and 7,8-dihydromethysticin are two major kavalactones in kava extract to induce CYP1A1.
Toxicological sciences : an official journal of the Society of Toxicology.
2011 Dec; 124(2):388-99. doi:
10.1093/toxsci/kfr235. [PMID: 21908763] - Yuma Iwai, Kouki Murakami, Yasuyuki Gomi, Toshihiro Hashimoto, Yoshinori Asakawa, Yoshinobu Okuno, Toyokazu Ishikawa, Dai Hatakeyama, Noriko Echigo, Takashi Kuzuhara. Anti-influenza activity of marchantins, macrocyclic bisbibenzyls contained in liverworts.
PloS one.
2011; 6(5):e19825. doi:
10.1371/journal.pone.0019825. [PMID: 21625478] - Valerie Robinson, Wilma F Bergfeld, Donald V Belsito, Curtis D Klaassen, James G Marks, Ronald C Shank, Thomas J Slaga, Paul W Snyder, F Alan Andersen. Final report on the safety assessment of Piper methysticum leaf/root/stem extract and Piper methysticum root extract.
International journal of toxicology.
2009 Nov; 28(6 Suppl):175S-88S. doi:
10.1177/1091581809350934. [PMID: 19966149] - Tran Dang Xuan, Masakazu Fukuta, Ao Chang Wei, Abdelnaser Abdelghany Elzaawely, Tran Dang Khanh, Shinkichi Tawata. Efficacy of extracting solvents to chemical components of kava (Piper methysticum) roots.
Journal of natural medicines.
2008 Apr; 62(2):188-94. doi:
10.1007/s11418-007-0203-2. [PMID: 18404321] - A Matthias, J T Blanchfield, K G Penman, K M Bone, I Toth, R P Lehmann. Permeability studies of Kavalactones using a Caco-2 cell monolayer model.
Journal of clinical pharmacy and therapeutics.
2007 Jun; 32(3):233-9. doi:
10.1111/j.1365-2710.2007.00810.x. [PMID: 17489874] - T D Xuan, A A Elzaawely, M Fukuta, S Tawata. Herbicidal and Fungicidal Activities of Lactones in Kava (Piper methysticum).
Journal of agricultural and food chemistry.
2006 Feb; 54(3):720-5. doi:
10.1021/jf0519461. [PMID: 16448174] - J Anke, S Fu, I Ramzan. Kavalactones fail to inhibit alcohol dehydrogenase in vitro.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2006 Feb; 13(3):192-5. doi:
10.1016/j.phymed.2004.07.005. [PMID: 16428028] - James M Mathews, Amy S Etheridge, John L Valentine, Sherry R Black, Donna P Coleman, Purvi Patel, James So, Leo T Burka. Pharmacokinetics and disposition of the kavalactone kawain: interaction with kava extract and kavalactones in vivo and in vitro.
Drug metabolism and disposition: the biological fate of chemicals.
2005 Oct; 33(10):1555-63. doi:
10.1124/dmd.105.004317. [PMID: 16033948] - Orapin Chienthavorn, Roger M Smith, Ian D Wilson, Brian Wright, Eva M Lenz. Superheated water chromatography-nuclear magnetic resonance spectroscopy of kava lactones.
Phytochemical analysis : PCA.
2005 May; 16(3):217-21. doi:
10.1002/pca.848. [PMID: 15997856] - Lihong Hu, Jin-Woo Jhoo, Catharina Y W Ang, Michael Dinovi, Antonia Mattia. Determination of six kavalactones in dietary supplements and selected functional foods containing Piper methysticum by isocratic liquid chromatography with internal standard.
Journal of AOAC International.
2005 Jan; 88(1):16-25. doi:
. [PMID: 15759721] - Lihong Zou, Martha R Harkey, Gary L Henderson, Laura E Dike. Kava does not display metabolic toxicity in a homogeneous cellular assay.
Planta medica.
2004 Apr; 70(4):289-92. doi:
10.1055/s-2004-818937. [PMID: 15095141] - L Zou, G L Henderson, M R Harkey, Y Sakai, A Li. Effects of kava (Kava-kava, 'Awa, Yaqona, Piper methysticum) on c-DNA-expressed cytochrome P450 enzymes and human cryopreserved hepatocytes.
Phytomedicine : international journal of phytotherapy and phytopharmacology.
2004; 11(4):285-94. doi:
10.1078/0944711041495263. [PMID: 15185840] - Matthias Unger, Ulrike Holzgrabe, Wolfgang Jacobsen, Carolyn Cummins, Leslie Z Benet. Inhibition of cytochrome P450 3A4 by extracts and kavalactones of Piper methysticum (Kava-Kava).
Planta medica.
2002 Dec; 68(12):1055-8. doi:
10.1055/s-2002-36360. [PMID: 12494328] - L D Dinh, U Simmen, K B Bueter, B Bueter, K Lundstrom, W Schaffner. Interaction of various Piper methysticum cultivars with CNS receptors in vitro.
Planta medica.
2001 Jun; 67(4):306-11. doi:
10.1055/s-2001-14334. [PMID: 11458444] - E A Abourashed, I A Khan. Microbial transformation of kawain and methysticin.
Chemical & pharmaceutical bulletin.
2000 Dec; 48(12):1996-8. doi:
10.1248/cpb.48.1996. [PMID: 11145158] - G Boonen, M A Beck, H Häberlein. Contribution to the quantitative and enantioselective determination of kavapyrones by high-performance liquid chromatography on ChiraSpher NT material.
Journal of chromatography. B, Biomedical sciences and applications.
1997 Nov; 702(1-2):240-4. doi:
10.1016/s0378-4347(97)00389-7. [PMID: 9449578] - C Backhauss, J Krieglstein. Extract of kava (Piper methysticum) and its methysticin constituents protect brain tissue against ischemic damage in rodents.
European journal of pharmacology.
1992 May; 215(2-3):265-9. doi:
10.1016/0014-2999(92)90037-5. [PMID: 1396990]
