(R)-Menthofuran (BioDeep_00000001067)

 

Secondary id: BioDeep_00000015317

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


(6R)-3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuran

化学式: C10H14O (150.1045)
中文名称: 薄荷呋喃, (+)-薄荷呋喃
谱图信息: 最多检出来源 Homo sapiens(lipidomics) 25.93%

分子结构信息

SMILES: C1Cc2c(C[C@@H]1C)occ2C
InChI: InChI=1S/C10H14O/c1-7-3-4-9-8(2)6-11-10(9)5-7/h6-7H,3-5H2,1-2H3

描述信息

Menthofuran is a monoterpenoid that is 4,5,6,7-tetrahydro-1-benzofuran substituted by methyl groups at positions 3 and 6. It has a role as a nematicide and a plant metabolite. It is a member of 1-benzofurans and a monoterpenoid.
Menthofuran is a natural product found in Methanobacterium and Mentha pulegium with data available.
Constituent of peppermint oil (Mentha piperita) and other Mentha subspecies as minor but essential organoleptic. It is used in peppermint oil formulations. (R)-Menthofuran is found in mentha (mint), orange mint, and herbs and spices.
(R)-Menthofuran is found in herbs and spices. (R)-Menthofuran is a constituent of peppermint oil (Mentha piperita) and other Mentha species as minor but essential organoleptic. (R)-Menthofuran is used in peppermint oil formulations
A monoterpenoid that is 4,5,6,7-tetrahydro-1-benzofuran substituted by methyl groups at positions 3 and 6.

同义名列表

32 个代谢物同义名

(6R)-3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuran; 4,5,6,7-Tetrahydro-3,6-dimethylbenzofuran, >=95\\%; 3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuran #; 4,5,6,7-Tetrahydro-3,6-dimethyl-(R)-Benzofuran; (R)-4,5,6,7-tetrahydro-3,6-dimethylbenzofuran; 3,6-Dimethyl-4,5,6,7-tetrahydro-1-benzofuran; 3,6-Dimethyl-4,5,6,7-tetrahydrobenzo[b]furan; BENZOFURAN, 4,5,6,7-TETRAHYDRO-3,6-DIMETHYL-; 3,6-dimethyl-4,5,6,7-tetrahydro-benzofuran; 4,5,6,7-TETRAHYDRO-3,6-DIMETHYL-BENZOFURAN; 3,6-dimethyl-4,5,6,7-tetrahydrobenzofuran; Benzofuran,5,6,7-tetrahydro-3,6-dimethyl-; 4,5,6,7-Tetrahydro-3,6-dimethylbenzofuran; 4,5,6,7-Tetrahydro-3,6-dimethylcoumarone; 3,9-Epoxy-(+)-p-Mentha-3,8-diene; (+)-3,9-Epoxy-P-mentha-3,8-diene; p-Mentha-3,8-diene, 3,9-epoxy-; 3,9-Epoxy-p-mentha-3,8-diene; menthofuran, (R)-isomer; p-Mentha-3, 3,9-epoxy-; MENTHOFURAN, (+/-)-; (R)-(+)-Menthofuran; (+/-)-menthofuran; UNII:LK024V9U3C; (+)-Menthofuran; (R)-Menthofuran; Menthofurane; Tox21_200722; Menthofuran; 3,8-diene; Menthofuran; Menthofuran



数据库引用编号

25 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)

72 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 11 CAT, CYP1A1, CYP2A6, CYP2C19, CYP2D6, CYP2E1, CYP3A4, HPGDS, MDH1, NR1I3, NR3C1
Peripheral membrane protein 3 CYP1A1, CYP1B1, CYP2E1
Endoplasmic reticulum membrane 8 CYP1A1, CYP1A2, CYP1B1, CYP2A6, CYP2C19, CYP2D6, CYP2E1, CYP3A4
Nucleus 4 MYB, NR1I2, NR1I3, NR3C1
cytosol 7 CAT, GPT, HPGDS, MDH1, MYB, NR1I3, NR3C1
nuclear body 1 NR1I2
centrosome 2 MDH1, NR3C1
nucleoplasm 5 HPGDS, MYB, NR1I2, NR1I3, NR3C1
RNA polymerase II transcription regulator complex 1 MYB
Synapse 1 NR3C1
Golgi membrane 1 INS
mitochondrial inner membrane 2 CYP1A1, CYP2E1
Cytoplasm, cytosol 1 MDH1
plasma membrane 2 CYP2C19, KNG1
Membrane 7 CAT, CYP1B1, CYP2A6, CYP2D6, CYP3A4, MYB, NR3C1
extracellular exosome 5 ALDH2, CAT, GPT, KNG1, MDH1
endoplasmic reticulum 1 CYP2D6
extracellular space 4 C1S, INS, KNG1, MDH1
mitochondrion 6 ALDH2, CAT, CYP1A1, CYP1B1, CYP2D6, NR3C1
protein-containing complex 2 CAT, NR3C1
intracellular membrane-bounded organelle 10 CAT, CYP1A1, CYP1A2, CYP1B1, CYP2A6, CYP2C19, CYP2D6, CYP2E1, CYP3A4, HPGDS
Microsome membrane 6 CYP1A1, CYP1A2, CYP1B1, CYP2D6, CYP2E1, CYP3A4
Secreted 1 INS
extracellular region 4 C1S, CAT, INS, KNG1
Single-pass membrane protein 1 CYP2D6
Mitochondrion matrix 1 ALDH2
mitochondrial matrix 3 ALDH2, CAT, NR3C1
transcription regulator complex 1 NR1I2
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 NR3C1
Mitochondrion inner membrane 2 CYP1A1, CYP2E1
Cytoplasm, cytoskeleton 1 NR1I3
Cytoplasm, cytoskeleton, spindle 1 NR3C1
focal adhesion 1 CAT
spindle 1 NR3C1
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 1 KNG1
nuclear speck 1 NR3C1
chromatin 3 NR1I2, NR1I3, NR3C1
Chromosome 1 NR3C1
cytoskeleton 1 NR1I3
Secreted, extracellular space 1 KNG1
blood microparticle 2 C1S, KNG1
endosome lumen 1 INS
Nucleus, nucleoplasm 1 NR3C1
intermediate filament cytoskeleton 1 NR1I2
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 INS, KNG1
nuclear matrix 1 MYB
platelet alpha granule lumen 1 KNG1
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
cytoplasmic microtubule 1 CYP2A6
[Isoform Alpha]: Cytoplasm 1 NR3C1
catalase complex 1 CAT
[Isoform Beta]: Nucleus 1 NR3C1
[Isoform Alpha-B]: Nucleus 1 NR3C1


文献列表

  • Guillaume Billerach, Laurent Rouméas, Eric Dubreucq, Hélène Fulcrand. Furanolysis with Menthofuran: A New Depolymerization Method for Analyzing Condensed Tannins. Journal of agricultural and food chemistry. 2020 Mar; 68(10):2917-2926. doi: 10.1021/acs.jafc.9b00497. [PMID: 31013083]
  • Zhe Li, Wenwen Wang, Guilong Li, Kai Guo, Paul Harvey, Quan Chen, Zhongjuan Zhao, Yanli Wei, Jishun Li, Hetong Yang. MAPK-mediated regulation of growth and essential oil composition in a salt-tolerant peppermint (Mentha piperita L.) under NaCl stress. Protoplasma. 2016 Nov; 253(6):1541-1556. doi: 10.1007/s00709-015-0915-1. [PMID: 26631016]
  • 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]
  • Birendra Kumar, Himanshi Mali, Ekta Gupta. Genetic variability, character association, and path analysis for economic traits in menthofuran rich half-sib seed progeny of Mentha piperita L. BioMed research international. 2014; 2014(?):150830. doi: 10.1155/2014/150830. [PMID: 24963471]
  • S Cyrus Khojasteh, Dylan P Hartley, Kevin A Ford, Hirdesh Uppal, Shimako Oishi, Sidney D Nelson. Characterization of rat liver proteins adducted by reactive metabolites of menthofuran. Chemical research in toxicology. 2012 Nov; 25(11):2301-9. doi: 10.1021/tx300144d. [PMID: 23106769]
  • Yanina Estefanía Rossi, Lilián Canavoso, Sara María Palacios. Molecular response of Musca domestica L. to Mintostachys verticillata essential oil, (4R)+-pulegone and menthone. Fitoterapia. 2012 Mar; 83(2):336-42. doi: 10.1016/j.fitote.2011.11.019. [PMID: 22155595]
  • Alessandra Bertoli, Michele Leonardi, Justyna Krzyzanowska, Wieslaw Oleszek, Luisa Pistelli. In vitro production of M. × piperita not containing pulegone and menthofuran. Acta biochimica Polonica. 2012; 59(3):417-23. doi: . [PMID: 22946028]
  • Maricel Valeria Santoro, Julio Zygadlo, Walter Giordano, Erika Banchio. Volatile organic compounds from rhizobacteria increase biosynthesis of essential oils and growth parameters in peppermint (Mentha piperita). Plant physiology and biochemistry : PPB. 2011 Oct; 49(10):1177-82. doi: 10.1016/j.plaphy.2011.07.016. [PMID: 21843946]
  • S Cyrus Khojasteh, Shimako Oishi, Sidney D Nelson. Metabolism and toxicity of menthofuran in rat liver slices and in rats. Chemical research in toxicology. 2010 Nov; 23(11):1824-32. doi: 10.1021/tx100268g. [PMID: 20945912]
  • Rigoberto Rios-Estepa, Glenn W Turner, James M Lee, Rodney B Croteau, B Markus Lange. A systems biology approach identifies the biochemical mechanisms regulating monoterpenoid essential oil composition in peppermint. Proceedings of the National Academy of Sciences of the United States of America. 2008 Feb; 105(8):2818-23. doi: 10.1073/pnas.0712314105. [PMID: 18287058]
  • Ling-Jen Chen Ferguson, Edward H Lebetkin, Fred B Lih, Kenneth B Tomer, Horace D Parkinson, Susan J Borghoff, Leo T Burka. 14C-labeled pulegone and metabolites binding to alpha2u-globulin in kidneys of male F-344 rats. Journal of toxicology and environmental health. Part A. 2007 Sep; 70(17):1416-23. doi: 10.1080/15287390701382720. [PMID: 17687727]
  • P Racine, B Auffray. Quenching of singlet molecular oxygen by Commiphora myrrha extracts and menthofuran. Fitoterapia. 2005 Jun; 76(3-4):316-23. doi: 10.1016/j.fitote.2005.03.017. [PMID: 15890469]
  • Soheil S Mahmoud, Rodney B Croteau. Menthofuran regulates essential oil biosynthesis in peppermint by controlling a downstream monoterpene reductase. Proceedings of the National Academy of Sciences of the United States of America. 2003 Nov; 100(24):14481-6. doi: 10.1073/pnas.2436325100. [PMID: 14623962]
  • Wolfgang Engel. In vivo studies on the metabolism of the monoterpene pulegone in humans using the metabolism of ingestion-correlated amounts (MICA) approach: explanation for the toxicity differences between (S)-(-)- and (R)-(+)-pulegone. Journal of agricultural and food chemistry. 2003 Oct; 51(22):6589-97. doi: 10.1021/jf034702u. [PMID: 14558782]
  • L-J Chen, E H Lebetkin, L T Burka. Metabolism of (R)-(+)-menthofuran in Fischer-344 rats: identification of sulfonic acid metabolites. Drug metabolism and disposition: the biological fate of chemicals. 2003 Oct; 31(10):1208-13. doi: 10.1124/dmd.31.10.1208. [PMID: 12975329]
  • M Maffei, W Camusso, S Sacco. Effect of Mentha x piperita essential oil and monoterpenes on cucumber root membrane potential. Phytochemistry. 2001 Nov; 58(5):703-7. doi: 10.1016/s0031-9422(01)00313-2. [PMID: 11672734]
  • C M Bertea, M Schalk, F Karp, M Maffei, R Croteau. Demonstration that menthofuran synthase of mint (Mentha) is a cytochrome P450 monooxygenase: cloning, functional expression, and characterization of the responsible gene. Archives of biochemistry and biophysics. 2001 Jun; 390(2):279-86. doi: 10.1006/abbi.2001.2378. [PMID: 11396930]
  • S Fuchs, S Zinn, T Beck, A Mosandl. Biosynthesis of menthofuran in Mentha x piperita: stereoselective and mechanistic studies. Journal of agricultural and food chemistry. 1999 Oct; 47(10):4100-5. doi: 10.1021/jf990439e. [PMID: 10552773]
  • B B Vadiraja, N W Gaikwad, K M Madyastha. Hepatoprotective effect of C-phycocyanin: protection for carbon tetrachloride and R-(+)-pulegone-mediated hepatotoxicty in rats. Biochemical and biophysical research communications. 1998 Aug; 249(2):428-31. doi: 10.1006/bbrc.1998.9149. [PMID: 9712713]
  • I B Anderson, W H Mullen, J E Meeker, Khojasteh-BakhtSC, S Oishi, S D Nelson, P D Blanc. Pennyroyal toxicity: measurement of toxic metabolite levels in two cases and review of the literature. Annals of internal medicine. 1996 Apr; 124(8):726-34. doi: 10.7326/0003-4819-124-8-199604150-00004. [PMID: 8633832]
  • K M Madyastha, C P Raj. Effects of menthofuran, a monoterpene furan on rat liver microsomal enzymes, in vivo. Toxicology. 1994 Apr; 89(2):119-25. doi: 10.1016/0300-483x(94)90220-8. [PMID: 8197589]
  • K M Madyastha, C P Raj. Metabolic fate of menthofuran in rats. Novel oxidative pathways. Drug metabolism and disposition: the biological fate of chemicals. 1992 Mar; 20(2):295-301. doi: . [PMID: 1352224]
  • K M Madyastha, C P Raj. Evidence for the formation of a known toxin, p-cresol, from menthofuran. Biochemical and biophysical research communications. 1991 May; 177(1):440-6. doi: 10.1016/0006-291x(91)92003-3. [PMID: 2043129]
  • D Thomassen, J T Slattery, S D Nelson. Menthofuran-dependent and independent aspects of pulegone hepatotoxicity: roles of glutathione. The Journal of pharmacology and experimental therapeutics. 1990 May; 253(2):567-72. doi: . [PMID: 2338648]
  • D Thomassen, J T Slattery, S D Nelson. Contribution of menthofuran to the hepatotoxicity of pulegone: assessment based on matched area under the curve and on matched time course. The Journal of pharmacology and experimental therapeutics. 1988 Mar; 244(3):825-9. doi: . [PMID: 3252034]
  • J A LEMLI. [Determination of menthone, menthol and menthofuran in essential oil of Mentha; localization of menthofuran in the plant]. Annales pharmaceutiques francaises. 1954 Apr; 12(4):275-81. doi: ". [PMID: 13189199]