Vomifoliol (BioDeep_00000000804)

 

Secondary id: BioDeep_00000014916

PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


2-Cyclohexen-1-one, 4-hydroxy-4-((1E,3R)-3-hydroxy-1-buten-1-yl)-3,5,5-trimethyl-, (4S)-rel-

化学式: C13H20O3 (224.14123700000002)
中文名称: 吐叶醇
谱图信息: 最多检出来源 Viridiplantae(plant) 0.11%

分子结构信息

SMILES: C1=C([C@](C(CC1=O)(C)C)(O)/C=C/[C@@H](C)O)C
InChI: InChI=1S/C13H20O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,10,14,16H,8H2,1-4H3/b6-5+

描述信息

A fenchane monoterpenoid that is 3,5,5-trimethylcyclohex-2-en-1-one substituted by a hydroxy and a (1E)-3-hydroxybut-1-en-1-yl group at position 4.
(6S,9R)-vomifoliol is a (6S)-vomifoliol with a R configuration for the hydroxy group at position 9. It has a role as a phytotoxin and a metabolite. It is an enantiomer of a (6R,9S)-vomifoliol.
Vomifoliol is a natural product found in Sida acuta, Macrococculus pomiferus, and other organisms with data available.
A (6S)-vomifoliol with a R configuration for the hydroxy group at position 9.

同义名列表

37 个代谢物同义名

Vomifoliol; 2-Cyclohexen-1-one, 4-hydroxy-4-((1E,3R)-3-hydroxy-1-buten-1-yl)-3,5,5-trimethyl-, (4S)-rel-; 2-Cyclohexen-1-one, 4-hydroxy-4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-, (R*,S*-(E))-(+/-)-; 2-Cyclohexen-1-one, 4-hydroxy-4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-, (S-(R*,S*-(E)))-; 2-Cyclohexen-1-one, 4-hydroxy-4-((1E,3R)-3-hydroxy-1-buten-1-yl)-3,5,5-trimethyl-, (4S)-; 4-Hydroxy-4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-2-cyclohexen-1-one, (4S,3R)-(E)-(+/-)-; 2-Cyclohexen-1-one, 4-hydroxy-4-((1E,3R)-3-hydroxy-1-butenyl)-3,5,5-trimethyl-, (4S)-; 2-Cyclohexen-1-one, 4-hydroxy-4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-, (R*,S*-(E))-; (4S)-4-hydroxy-4-[(1E,3R)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one; (S)-4-Hydroxy-4-((R,E)-3-hydroxybut-1-en-1-yl)-3,5,5-trimethylcyclohex-2-en-1-one; (4S)-4-hydroxy-4-[(1E,3R)-3-hydroxybut-1-enyl]-3,5,5-trimethylcyclohex-2-en-1-one; (4S)-4-hydroxy-4-[(E,3R)-3-hydroxybut-1-enyl]-3,5,5-trimethylcyclohex-2-en-1-one; 2-Cyclohexen-1-one, 4-hydroxy-4-(3-hydroxy-1-butenyl)-3,5,5-trimethyl-, (+-)-; 2-CYCLOHEXEN-1-ONE, 4-HYDROXY-4-(3-HYDROXY-1-BUTENYL)-3,5,5-TRIMETHYL-, (+)-; (6S,7E,9R)-6,9-dihydroxy-4,7-megastigmadien-3-one; (6S,9R)-6-HYDROXY-3-OXO-.ALPHA.-IONOL; (6S,9R)-6-hydroxy-3-oxo-alpha-ionol; (+-)-6-hydroxy-3-oxo-alpha-ionol; KPQMCAKZRXOZLB-KOIHBYQTSA-N; (6S,9R)-vomifoliol; Roseoside aglycon; Vomifoliol, (+-)-; Vomifoliol, (+)-; (+/-)-Volifoliol; (+/-)-Blumenol-A; (+-)-Vomifoliol; UNII-B7QV234K84; (+-)-Blumenol A; (+)-BLUMENOL A; (+)-Vomifoliol; BLUMENOL A; B7QV234K84; (4S)-4-hydroxy-4-[(E,3R)-3-hydroxybut-1-enyl]-3,5,5-trimethyl-cyclohex-2-en-1-one; (4S)-4-hydroxy-4-[(E,3R)-3-hydroxybut-1-enyl]-3,5,5-trimethyl-1-cyclohex-2-enone; 23526-45-6; C01760; (6S,9R)-Vomifoliol



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)

86 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

  • Xuexia Zhang, Gang Li, Qin Deng, Zhiyong Xu, Juren Cen, Jing Xu. Vomifoliol isolated from mangrove plant Ceriops tagal inhibits the NFAT signaling pathway with CN as the target enzyme in vitro. Bioorganic & medicinal chemistry letters. 2021 09; 48(?):128235. doi: 10.1016/j.bmcl.2021.128235. [PMID: 34216746]
  • Abdul Rahim, Yohei Saito, Shuichi Fukuyoshi, Katsunori Miyake, Masuo Goto, Chin-Ho Chen, Gemini Alam, Kuo-Hsiung Lee, Kyoko Nakagawa-Goto. Paliasanines A-E, 3,4-Methylenedioxyquinoline Alkaloids Fused with a Phenyl-14-oxabicyclo[3.2.1]octane Unit from Melochia umbellata var. deglabrata. Journal of natural products. 2020 10; 83(10):2931-2939. doi: 10.1021/acs.jnatprod.0c00454. [PMID: 32946697]
  • Yulin Ren, Gerardo D Anaya-Eugenio, Austin A Czarnecki, Tran Ngoc Ninh, Chunhua Yuan, Hee-Byung Chai, Djaja D Soejarto, Joanna E Burdette, Esperanza J Carcache de Blanco, A Douglas Kinghorn. Cytotoxic and NF-κB and mitochondrial transmembrane potential inhibitory pentacyclic triterpenoids from Syzygium corticosum and their semi-synthetic derivatives. Bioorganic & medicinal chemistry. 2018 08; 26(15):4452-4460. doi: 10.1016/j.bmc.2018.07.025. [PMID: 30057155]
  • Di Zhou, Hongyan Wei, Zhe Jiang, Xuezheng Li, Kun Jiao, Xiaoguang Jia, Yue Hou, Ning Li. Natural potential neuroinflammatory inhibitors from Alhagi sparsifolia Shap. Bioorganic & medicinal chemistry letters. 2017 02; 27(4):973-978. doi: 10.1016/j.bmcl.2016.12.075. [PMID: 28073678]
  • Nina Corlay, Leen Delang, Emmanuelle Girard-Valenciennes, Johan Neyts, Patricia Clerc, Jacqueline Smadja, Françoise Guéritte, Pieter Leyssen, Marc Litaudon. Tigliane diterpenes from Croton mauritianus as inhibitors of chikungunya virus replication. Fitoterapia. 2014 Sep; 97(?):87-91. doi: 10.1016/j.fitote.2014.05.015. [PMID: 24879904]
  • Ngoc Vinh Huynh, Thi Hoai Thu Nguyen, Kim Phi Phung Nguyen, Poul Erik Hansen. Structural studies of the chemical constituents of Tithonia tagetiflora Desv. (Asteraceae). Magnetic resonance in chemistry : MRC. 2013 Jul; 51(7):439-43. doi: 10.1002/mrc.3963. [PMID: 23681665]
  • Jong Hoon Ahn, Eun Sil Kim, Chul Lee, Soonok Kim, Soo-Hyun Cho, Bang Yeon Hwang, Mi Kyeong Lee. Chemical constituents from Nelumbo nucifera leaves and their anti-obesity effects. Bioorganic & medicinal chemistry letters. 2013 Jun; 23(12):3604-8. doi: 10.1016/j.bmcl.2013.04.013. [PMID: 23642481]
  • Chrysoula Spanou, Aristidis S Veskoukis, Thalia Kerasioti, Maria Kontou, Apostolos Angelis, Nektarios Aligiannis, Alexios-Leandros Skaltsounis, Dimitrios Kouretas. Flavonoid glycosides isolated from unique legume plant extracts as novel inhibitors of xanthine oxidase. PloS one. 2012; 7(3):e32214. doi: 10.1371/journal.pone.0032214. [PMID: 22396752]
  • Naisheng Bai, Kan He, Marc Roller, Ching-Shu Lai, Xi Shao, Min-Hsiung Pan, Antoine Bily, Chi-Tang Ho. Flavonoid glycosides from Microtea debilis and their cytotoxic and anti-inflammatory effects. Fitoterapia. 2011 Mar; 82(2):168-72. doi: 10.1016/j.fitote.2010.08.014. [PMID: 20804824]
  • Igor Jerković, Gordana Hegić, Zvonimir Marijanović, Dragan Bubalo. Organic extractives from Mentha spp. honey and the bee-stomach: methyl syringate, vomifoliol, terpenediol I, hotrienol and other compounds. Molecules (Basel, Switzerland). 2010 Apr; 15(4):2911-24. doi: 10.3390/molecules15042911. [PMID: 20428087]
  • Ya-Ling Song, Li Zhang, Jin-Ming Gao, Guan-Hua Du, Yong-Xian Cheng. Speciosaperoxide, a new triterpene acid, and other terpenoids from Chaenomeles speciosa. Journal of Asian natural products research. 2008 Mar; 10(3-4):217-22. doi: 10.1080/10286020701395370. [PMID: 18335336]
  • Olga Alvarez Colom, Susana Popich, Alicia Bardon. Bioactive constituents from Rollinia emarginata (Annonaceae). Natural product research. 2007 Mar; 21(3):254-9. doi: 10.1080/14786410500462819. [PMID: 17365716]
  • T Kanchanapoom, A Sirikatitham, H Otsuka, S Ruchirawat. Cuneatoside, a new megastigmane diglycoside from Erythroxylum cuneatum Blume. Journal of Asian natural products research. 2006 Dec; 8(8):747-51. doi: 10.1080/10286020500246519. [PMID: 17145665]
  • Nian-Yun Yang, Jin-Ao Duan, Ping Li, Shi-Hui Qian. Chemical constituents of Glechoma longituba. Yao xue xue bao = Acta pharmaceutica Sinica. 2006 May; 41(5):431-4. doi: . [PMID: 16848319]
  • Suporn Phommart, Pakawadee Sutthivaiyakit, Nitirat Chimnoi, Somsak Ruchirawat, Somyote Sutthivaiyakit. Constituents of the leaves of Macaranga tanarius. Journal of natural products. 2005 Jun; 68(6):927-30. doi: 10.1021/np0500272. [PMID: 15974621]
  • Ayben Kilic, Hubert Kollmannsberger, Siegfried Nitz. Glycosidically bound volatiles and flavor precursors in Laurus nobilis L. Journal of agricultural and food chemistry. 2005 Mar; 53(6):2231-5. doi: 10.1021/jf040373+. [PMID: 15769161]
  • Marinella De Leo, Alessandra Braca, Nunziatina De Tommasi, Ivan Norscia, Ivano Morelli, Lucia Battinelli, Gabriela Mazzanti. Phenolic compounds from Baseonema acuminatum leaves: isolation and antimicrobial activity. Planta medica. 2004 Sep; 70(9):841-6. doi: 10.1055/s-2004-827233. [PMID: 15503354]
  • S Hammami, H Ben Jannet, A Bergaoui, L Ciavatta, G Cimino, Z Mighri. Isolation and structure elucidation of a flavanone, a flavanone glycoside and vomifoliol from Echiochilon fruticosum growing in Tunisia. Molecules (Basel, Switzerland). 2004 Jun; 9(7):602-8. doi: 10.3390/90700602. [PMID: 18007460]
  • Dae Sik Jang, Eun Jung Park, Young-Hwa Kang, Bao-Ning Su, Michael E Hawthorne, Jose Schunke Vigo, James G Graham, Fernando Cabieses, Harry H S Fong, Rajendra G Mehta, John M Pezzuto, A Douglas Kinghorn. Compounds obtained from sida acuta with the potential to induce quinone reductase and to inhibit 7,12-dimethylbenz[a]anthracene-induced preneoplastic lesions in a mouse mammary organ culture model. Archives of pharmacal research. 2003 Aug; 26(8):585-90. doi: 10.1007/bf02976704. [PMID: 12967190]