Nonivamide (BioDeep_00000017240)

 

Secondary id: BioDeep_00000402548

human metabolite PANOMIX_OTCML-2023 Endogenous Chemicals and Drugs


代谢物信息卡片


NonivamideAnemarsaponin EAnhydrosecoisolariciresinolConessineQuercetin-3-O-β-D-glucose-7-O-β-D-gentiobiosidenCornuside4-AllylcatecholZingibereneConiferinSchisantherin EVomifoliol5-MethylfurfuralWithanoneMauritianinGardenin B

化学式: C17H27NO3 (293.1990832)
中文名称: 辣椒素(合成), 诺香草胺, 辣椒素
谱图信息: 最多检出来源 Viridiplantae(plant) 0.64%

分子结构信息

SMILES: C1=CC(CNC(=O)CCCCCCCC)=CC(OC)=C1O
InChI: InChI=1S/C17H27NO3/c1-3-4-5-6-7-8-9-17(20)18-13-14-10-11-15(19)16(12-14)21-2/h10-12,19H,3-9,13H2,1-2H3,(H,18,20)

描述信息

Nonivamide, also known as pseudocapsaicin or hansaplast, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Nonivamide is odorless and a bland tasting compound. Nonivamide is found, on average, in the highest concentration within a few different foods, such as yellow bell peppers, red bell peppers, and pepper (C. frutescens) and in a lower concentration in pepper (C. annuum), orange bell peppers, and green bell peppers. Nonivamide has also been detected, but not quantified, in herbs and spices. This could make nonivamide a potential biomarker for the consumption of these foods. Limited information is available on pharmacokinetics and metabolism of nonivamide. Agonism of the VR1 (TRPV1) (vanilloid) receptor by Nonivamide was demonstrated to induce the release of Ca2+ from the endoplasmic reticulum (ER) of human lung cells, producing ER stress and cell death . The cardiovascular effects are partly explained by substance P release. Administered intraperitoneally, the LD50 in rats was measured to be about 90 mg/kg. Nonivamide has been shown to stimulate afferent neurons with about half the potency of Capsaicin (PMID:6202305).
Nonivamide is a capsaicinoid that is the carboxamide resulting from the formal condensation of the amino group of 4-hydroxy-3-methoxybenzylamine with the carboxy group of nonanoic acid. It is the active ingredient in many pepper sprays. It has a role as a lachrymator. It is a capsaicinoid and a member of phenols.
Nonivamide is found in herbs and spices. It is an alkaloid from the Capsicum species. The structures of [DB06774] and nonivamide differ only slightly with respect to the fatty acid moiety of the side chain (8-methyl nonenoic acid versus nonanoic acid). Nonivamide is a flavoring ingredient. Nonivamide is an organic compound and a capsaicinoid. It is an amide of pelargonic acid and vanillylamine. It is naturally found in chili peppers but manufactured to produce a synthetic form for various pharmacologic preparations. This drug has been studied in combination with Nicarboxil in the treatment of lower back pain. Nonivamide has also been studied for its anti-inflammatory properties, as well as in fat loss therapies and has demonstrated promising results,,,.
Nonivamide is a natural product found in Capsicum annuum with data available.
See also: Paprika (part of); Methyl salicylate; nonivamide (component of) ... View More ...
A capsaicinoid that is the carboxamide resulting from the formal condensation of the amino group of 4-hydroxy-3-methoxybenzylamine with the carboxy group of nonanoic acid. It is the active ingredient in many pepper sprays.
Alkaloid from Capsicum subspecies Flavouring ingredient
Nonivamide is a Nonivamide is a

同义名列表

92 个代谢物同义名

NonivamideAnemarsaponin EAnhydrosecoisolariciresinolConessineQuercetin-3-O-β-D-glucose-7-O-β-D-gentiobiosidenCornuside4-AllylcatecholZingibereneConiferinSchisantherin EVomifoliol5-MethylfurfuralWithanoneMauritianinGardenin B; Nonivamide; Pseudocapsaicin; PAVA; Pelargonic acid vallinylamide; Vanillyl N-nonylamide; Nonivamide, European Pharmacopoeia (EP) Reference Standard; N-[(4-Hydroxy-3-methoxyphenyl)methyl]nonanamide, 9CI; Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-; Nonanamide, N-((4-hydroxy-3-methoxyphenyl)methyl)-; N-NONANOYL-4-HYDROXY-3-METHOXYBENZYL-AMIDE [FHFI]; N-[(4-Hydroxy-3-methoxyphenyl)methyl]-Nonanamide; N-((4-Hydroxy-3-methoxyphenyl)methyl)-Nonanamide; N-((4-Hydroxy-3-methoxyphenyl)methyl)nonanamide; N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide; N-((Hydroxy-3-methoxyphenyl)methyl)4-nonanamide; 4-Hydroxy-3-methoxy-N-(1-oxononyl)-Benzamide; Nonanamide, N-(4-hydroxy-3-methoxybenzyl)-; N-NONANOYL-4-HYDROXY-3-METHOXYBENZYL-AMIDE; NONIVAMIDE (CONSTITUENT OF CAPSICUM) [DSC]; N-(4-Hydroxy-3-methoxybenzyl)nonanamide #; N-Vanillylnonanamide, analytical standard; HYDROXYMETHOXYBENZYL PELARGONAMIDE [INCI]; N-(4-Hydroxy-3-methoxybenzyl)nonanamide; Nonanoyl 4-hydroxy-3-methoxybenzylamide; N-Vanillylnonanamide, >=97\\%, powder; NONIVAMIDE (CONSTITUENT OF CAPSICUM); Hydroxymethoxybenzyl pelargonamide; N-Pelargonic Acid Vanillylamide; Pelargonic acid vanillylamide; Nonanoic acid vanillylamide; Nonylic acid vanillylamide; desmethyldihydrocapsaicin; N-Vanillylnonanamide, 8CI; Vanillyl pelargonic amide; Pelargonoyl vanillylamide; N-Pelargonylvanillylamide; Nonylic acid vanillyamide; Nonivamida (INN-Spanish); N-Nonanoyl vanillylamide; Nonivamida [INN-Spanish]; Pelargonyl vanillylamide; Nonivamidum [INN-Latin]; Nonanamide, N-vanillyl-; Nonanoate vanillylamide; N-Vanillylpelargonamide; Nonivamidum (INN-Latin); Nonanoylvanillyl Amide; Nonanoyl vanillylamide; Vanillyl n-nonoylamide; Vanillyl n-Nonylamide; N-vanillyl nonanamide; N-vanillyl-nonanamide; N-Vanillylnonanoamide; vanillyl-N-nonylamide; Capsaicin (Synthetic); 8-Nordihydrocapsaicin; Nonoyl vanillylamide; N-vanillylnonanamide; Synthetic capsaicin; Nonylic vanillamide; N-vanillyl-nonamide; NONIVAMIDE [WHO-DD]; NONIVAMIDE [MART.]; vanillylnonanamide; NONIVAMIDE (MART.); N-Vanillylnonamide; N-Nonylvanylamide; Spectrum5_001853; Spectrum4_000916; Spectrum2_001091; vanillylnonamide; Nonivamide [INN]; Nonivamide (INN); Pseudocapsaicin; Hansaplast (TN); Nonylvanylamide; Tox21_110302_1; Lopac0_001218; DivK1c_006895; KBio1_001839; KBio2_003359; KBio2_000791; Tox21_301218; KBio2_005927; Tox21_110302; Nonivamidum; Hansaplast; Nonivamida; PAVA spray; Nonivamide; NA 17:4;O2; FEMA 2787; HH 50; PAVA; PSVA



数据库引用编号

20 个数据库交叉引用编号

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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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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

  • 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]
  • 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]
  • Christina M Hochkogler, Barbara Lieder, Petra Rust, David Berry, Samuel M Meier, Marc Pignitter, Alessandra Riva, Alina Leitinger, Anne Bruk, Simone Wagner, Joachim Hans, Sabine Widder, Jakob P Ley, Gerhard E Krammer, Veronika Somoza. A 12-week intervention with nonivamide, a TRPV1 agonist, prevents a dietary-induced body fat gain and increases peripheral serotonin in moderately overweight subjects. Molecular nutrition & food research. 2017 05; 61(5):. doi: 10.1002/mnfr.201600731. [PMID: 28012242]
  • Qingqing Yang, Jianguo Zhu, Fei Ma, Peiwu Li, Liangxiao Zhang, Wen Zhang, Xiaoxia Ding, Qi Zhang. Quantitative determination of major capsaicinoids in serum by ELISA and time-resolved fluorescent immunoassay based on monoclonal antibodies. Biosensors & bioelectronics. 2016 Jul; 81(?):229-235. doi: 10.1016/j.bios.2016.02.074. [PMID: 26954788]
  • Barbara Rohm, Annett Riedel, Jakob P Ley, Sabine Widder, Gerhard E Krammer, Veronika Somoza. Capsaicin, nonivamide and trans-pellitorine decrease free fatty acid uptake without TRPV1 activation and increase acetyl-coenzyme A synthetase activity in Caco-2 cells. Food & function. 2015 Jan; 6(1):173-85. doi: 10.1039/c4fo00435c. [PMID: 25422952]
  • Christina M Hochkogler, Barbara Rohm, Karin Hojdar, Marc Pignitter, Sabine Widder, Jakob P Ley, Gerhard E Krammer, Veronika Somoza. The capsaicin analog nonivamide decreases total energy intake from a standardized breakfast and enhances plasma serotonin levels in moderately overweight men after administered in an oral glucose tolerance test: a randomized, crossover trial. Molecular nutrition & food research. 2014 Jun; 58(6):1282-90. doi: 10.1002/mnfr.201300821. [PMID: 24753478]
  • Min Gi Kim, Beom Soo Shin, Yohan Choi, Jae Kuk Ryu, Seung Woo Shin, Hyun Wook Choo, Sun Dong Yoo. Determination and pharmacokinetics of [6]-gingerol in mouse plasma by liquid chromatography-tandem mass spectrometry. Biomedical chromatography : BMC. 2012 May; 26(5):660-5. doi: 10.1002/bmc.1712. [PMID: 22095468]
  • Antonella Rosa, Giovanni Appendino, M Paola Melis, Monica Deiana, Angela Atzeri, Incani Alessandra, Alberto Minassi, M Assunta Dessì. Protective effect and relation structure-activity of nonivamide and iododerivatives in several models of lipid oxidation. Chemico-biological interactions. 2009 Jul; 180(2):183-92. doi: 10.1016/j.cbi.2009.01.002. [PMID: 19497416]
  • Karen C Thomas, Ashwini S Sabnis, Mark E Johansen, Diane L Lanza, Philip J Moos, Garold S Yost, Christopher A Reilly. Transient receptor potential vanilloid 1 agonists cause endoplasmic reticulum stress and cell death in human lung cells. The Journal of pharmacology and experimental therapeutics. 2007 Jun; 321(3):830-8. doi: 10.1124/jpet.107.119412. [PMID: 17332266]
  • Maj-Britt Angarano, Robert F McMahon, Doyle L Hawkins, John A Schetz. Exploration of structure-antifouling relationships of capsaicin-like compounds that inhibit zebra mussel (Dreissena polymorpha) macrofouling. Biofouling. 2007; 23(5-6):295-305. doi: 10.1080/08927010701371439. [PMID: 17852065]
  • Xiu-Yu Yi, Victoria X Li, Fan Zhang, Fan Yi, Daniel R Matson, Ming Tao Jiang, Pin-Lan Li. Characteristics and actions of NAD(P)H oxidase on the sarcoplasmic reticulum of coronary artery smooth muscle. American journal of physiology. Heart and circulatory physiology. 2006 Mar; 290(3):H1136-44. doi: 10.1152/ajpheart.00296.2005. [PMID: 16227345]
  • Mark E Johansen, Christopher A Reilly, Garold S Yost. TRPV1 antagonists elevate cell surface populations of receptor protein and exacerbate TRPV1-mediated toxicities in human lung epithelial cells. Toxicological sciences : an official journal of the Society of Toxicology. 2006 Jan; 89(1):278-86. doi: 10.1093/toxsci/kfi292. [PMID: 16120755]
  • Nobuyuki Kozukue, Jae-Sook Han, Etsuko Kozukue, Sin-Jung Lee, Joung-Ae Kim, Kap-Rang Lee, Carol E Levin, Mendel Friedman. Analysis of eight capsaicinoids in peppers and pepper-containing foods by high-performance liquid chromatography and liquid chromatography-mass spectrometry. Journal of agricultural and food chemistry. 2005 Nov; 53(23):9172-81. doi: 10.1021/jf050469j. [PMID: 16277419]
  • Robert Q Thompson, Karen W Phinney, Michael J Welch, Edward White. Quantitative determination of capsaicinoids by liquid chromatography-electrospray mass spectrometry. Analytical and bioanalytical chemistry. 2005 Apr; 381(7):1441-51. doi: 10.1007/s00216-005-3102-y. [PMID: 15803309]
  • Edyta Niemczyk, Anna Majczak, Anna Hallmann, Jakub Kedzior, Michał Woźniak, Takashi Wakabayashi. A possible involvement of plasma membrane NAD(P)H oxidase in the switch mechanism of the cell death mode from apoptosis to necrosis in menadione-induced cell injury. Acta biochimica Polonica. 2004; 51(4):1015-22. doi: 0451041015. [PMID: 15625573]
  • H Tsuchiya. Biphasic membrane effects of capsaicin, an active component in Capsicum species. Journal of ethnopharmacology. 2001 May; 75(2-3):295-9. doi: 10.1016/s0378-8741(01)00200-8. [PMID: 11297867]
  • G B Kasting, W R Francis, L A Bowman, G O Kinnett. Percutaneous absorption of vanilloids: in vivo and in vitro studies. Journal of pharmaceutical sciences. 1997 Jan; 86(1):142-6. doi: 10.1021/js950484a. [PMID: 9002474]
  • P A Durant, T L Yaksh. Micturition in the unanesthetized rat: effects of intrathecal capsaicin, N-vanillylnonanamide, 6-hydroxydopamine and 5,6-dihydroxytryptamine. Brain research. 1988 Jun; 451(1-2):301-8. doi: 10.1016/0006-8993(88)90775-5. [PMID: 3150817]
  • G Skofitsch, J Donnerer, F Lembeck. Comparison of nonivamide and capsaicin with regard to their pharmacokinetics and effects on sensory neurons. Arzneimittel-Forschung. 1984; 34(2):154-6. doi: NULL. [PMID: 6202305]