Inuviscolide (BioDeep_00000396185)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


(3aR,4aR,5R,7aS,9aS)-5-hydroxy-5-methyl-3,8-dimethylidenedecahydroazuleno[6,5-b]furan-2(3H)-one

化学式: C15H20O3 (248.1412)
中文名称:
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C=C1C[C@@H]2OC(=O)C(=C)[C@H]2C[C@@H]2[C@@H]1CC[C@@]2(C)O
InChI: InChI=1S/C15H20O3/c1-8-6-13-11(9(2)14(16)18-13)7-12-10(8)4-5-15(12,3)17/h10-13,17H,1-2,4-7H2,3H3/t10-,11-,12-,13+,15-/m1/s1

描述信息

Inuviscolide is a sesquiterpene lactone that is decahydroazuleno[6,5-b]furan-2(3H)-one substituted by a hydroxy group at position 5, a methyl group at position 5 and methylidene groups at positions 3 and 8 (the 3aR,4aR,5R,7aS,9aS stereoisomer). Isolated from the aerial parts of Inula hupehensis, it exhibits anti-inflammatory activity. It has a role as an anti-inflammatory agent and a plant metabolite. It is a gamma-lactone, an organic heterotricyclic compound, a sesquiterpene lactone and a tertiary alcohol.
Inuviscolide is a natural product found in Helichrysum dasyanthum, Pulicaria incisa, and other organisms with data available.
A sesquiterpene lactone that is decahydroazuleno[6,5-b]furan-2(3H)-one substituted by a hydroxy group at position 5, a methyl group at position 5 and methylidene groups at positions 3 and 8 (the 3aR,4aR,5R,7aS,9aS stereoisomer). Isolated from the aerial parts of Inula hupehensis, it exhibits anti-inflammatory activity.

同义名列表

3 个代谢物同义名

(3aR,4aR,5R,7aS,9aS)-5-hydroxy-5-methyl-3,8-dimethylidenedecahydroazuleno[6,5-b]furan-2(3H)-one; 5-Hydroxy-5-methyl-3,8-dimethylidenedecahydroazuleno[6,5-b]furan-2(3H)-one; Inuviscolide



数据库引用编号

9 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)

46 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


文献列表

  • Sara Kebbi, Maria Letizia Ciavatta, Ali Mokhtar Mahmoud, Marianna Carbone, Alessia Ligresti, Ramdane Seghiri, Margherita Gavagnin. Sesquiterpene Lactones with the 12,8-Guaianolide Skeleton from Algerian Centaurea omphalotricha. Biomolecules. 2021 07; 11(7):. doi: 10.3390/biom11071053. [PMID: 34356677]
  • Young-Eun Ko, Sei-Ryang Oh, Hyuk-Hwan Song, Hyung Won Ryu, Sun-yung Ly, Jae Wha Kim. The effect of 4α,5α-epoxy-10α,14-dihydro-inuviscolide, a novel immunosuppressant isolated from Carpesium abrotanoides, on the cytokine profile in vitro and in vivo. International immunopharmacology. 2015 Mar; 25(1):121-9. doi: 10.1016/j.intimp.2015.01.002. [PMID: 25596339]
  • Ping-an Liu, Min Liu, Wei-wei Pan, Wei-jun He, Shuai Peng, Xiao-jiang Zhou. [Study on Chemical Constituents from Carpesium abrotanoides]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2014 Dec; 37(12):2213-5. doi: . [PMID: 26080506]
  • Xiangrong Cheng, Qi Zeng, Jie Ren, Jiangjiang Qin, Shoude Zhang, Yunheng Shen, Jiaxian Zhu, Fei Zhang, Ruijie Chang, Yan Zhu, Weidong Zhang, Huizi Jin. Sesquiterpene lactones from Inula falconeri, a plant endemic to the Himalayas, as potential anti-inflammatory agents. European journal of medicinal chemistry. 2011 Nov; 46(11):5408-15. doi: 10.1016/j.ejmech.2011.08.047. [PMID: 21924800]
  • Sharon Rozenblat, Shlomo Grossman, Margalit Bergman, Hugo Gottlieb, Yigal Cohen, Sara Dovrat. Induction of G2/M arrest and apoptosis by sesquiterpene lactones in human melanoma cell lines. Biochemical pharmacology. 2008 Jan; 75(2):369-82. doi: 10.1016/j.bcp.2007.08.024. [PMID: 17919456]
  • Salvador Máñez, Victoriano Hernández, Rosa-María Giner, José-Luis Ríos, María Del Carmen Recio. Inhibition of pro-inflammatory enzymes by inuviscolide, a sesquiterpene lactone from Inula viscosa. Fitoterapia. 2007 Jun; 78(4):329-31. doi: 10.1016/j.fitote.2007.03.005. [PMID: 17490829]
  • V Hernández, M del Carmen Recio, S Máñez, J M Prieto, R M Giner, J L Ríos. A mechanistic approach to the in vivo anti-inflammatory activity of sesquiterpenoid compounds isolated from Inula viscosa. Planta medica. 2001 Nov; 67(8):726-31. doi: 10.1055/s-2001-18342. [PMID: 11731914]
  • S Máñez, M C Recio, I Gil, C Gómez, R M Giner, P G Waterman, J L Ríos. A glycosyl analogue of diacylglycerol and other antiinflammatory constituents from Inula viscosa. Journal of natural products. 1999 Apr; 62(4):601-4. doi: 10.1021/np980132u. [PMID: 10217718]