Dihydroartemisinic (BioDeep_00000000398)

 

Secondary id: BioDeep_00000255305

PANOMIX_OTCML-2023 Chemicals and Drugs


代谢物信息卡片


2-(4,7-dimethyl-(1alpha-H),2,3,(4beta-H),(4aalpha-H),5,6,(8aalpha-H)-octahydronaphthalen-1-yl)propionic acid

化学式: C15H24O2 (236.1776)
中文名称: 二氢青蒿酸, 双氢青蒿酸
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 77.42%

分子结构信息

SMILES: CC1=C[C@H]2[C@@H](CC1)[C@H](C)CC[C@H]2[C@@H](C)C(=O)O
InChI: InChI=1S/C15H24O2/c1-9-4-6-12-10(2)5-7-13(14(12)8-9)11(3)15(16)17/h8,10-14H,4-7H2,1-3H3,(H,16,17)/t10-,11-,12+,13+,14+/m1/s1

描述信息

Dihydroartemisinic acid is a monocarboxylic acid that is propanoic acid substituted at position 2 by a (1S,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl group. It is a sesquiterpenoid precursor of the antimalarial drug, artemisinin. It has a role as a plant metabolite. It is a carbobicyclic compound, a monocarboxylic acid, a member of octahydronaphthalenes and a sesquiterpenoid. It is a conjugate acid of a dihydroartemisinate.
Dihydroartemisinic acid is a natural product found in Artemisia apiacea, Artemisia annua, and Artemisia carvifolia with data available.
A monocarboxylic acid that is propanoic acid substituted at position 2 by a (1S,4R,4aS,8aR)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl group. It is a sesquiterpenoid precursor of the antimalarial drug, artemisinin.
D009676 - Noxae > D016877 - Oxidants > D010545 - Peroxides
Dihydroartemisinic acid (Dihydroqinghao acid) is a biosynthetic precursor to the antimalarial agent Artemisinin[1].
Dihydroartemisinic acid (Dihydroqinghao acid) is a biosynthetic precursor to the antimalarial agent Artemisinin[1].

同义名列表

13 个代谢物同义名

2-(4,7-dimethyl-(1alpha-H),2,3,(4beta-H),(4aalpha-H),5,6,(8aalpha-H)-octahydronaphthalen-1-yl)propionic acid; (2R)-2-[(1R)-4beta,7-Dimethyl-1,2,3,4,4abeta,5,6,8abeta-octahydronaphthalen-1alpha-yl]propionic acid; (2R)-2-[(1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl]propanoic Acid; (R)-2-((1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)propanoic acid; (R)-2-((1R,4R,4aS,8aS)-4,7-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-1-yl)propanoicacid; (-)-dihydroartemisinic acid; JYGAZEJXUVDYHI-DGTMBMJNSA-N; dihydro artemisinic acid; Dihydro-artmisinic acid; Dihydroartemisinic acid; dihydroarteannuic acid; Dihydroqinghao acid; Dihydroartemisinic



数据库引用编号

11 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)

5 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

  • Meng-Yue Wang, Hui-Hua Wan, Li Xiang, Yu-Ting Pu, Qing-Gang Yin, Ran-Ran Gao, Yu-Hua Shi, Lan Wu. [Simultaneous determination of seven artemisinin-related compounds in Artemisia annua by UPLC-QQQ-MS/MS]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2024 Mar; 49(5):1260-1265. doi: 10.19540/j.cnki.cjcmm.2023105.101. [PMID: 38621973]
  • Rika Judd, Yilun Dong, Xiaoyan Sun, Yue Zhu, Mingzhuo Li, De-Yu Xie. Metabolic engineering of the anthocyanin biosynthetic pathway in Artemisia annua and relation to the expression of the artemisinin biosynthetic pathway. Planta. 2023 Feb; 257(3):63. doi: 10.1007/s00425-023-04091-6. [PMID: 36807538]
  • Delong Wang, Min Li, Chunxia Yuan, Yali Fang, Zhijia Zhang. Bioassay-Guided Isolation of Nematicidal Artemisinic Acid and Dihydroartemisinic Acid from Artemisia annua L. and Evaluation of Their Activity against Meloidogyne incognita. Chemistry & biodiversity. 2022 May; 19(5):e202200083. doi: 10.1002/cbdv.202200083. [PMID: 35344268]
  • Kaitlyn Varela, Hafij Al Mahmud, Hadi D Arman, Luis R Martinez, Catherine A Wakeman, Francis K Yoshimoto. Autoxidation of a C2-Olefinated Dihydroartemisinic Acid Analogue to Form an Aromatic Ring: Application to Serrulatene Biosynthesis. Journal of natural products. 2022 04; 85(4):951-962. doi: 10.1021/acs.jnatprod.1c01101. [PMID: 35357832]
  • Kaitlyn Varela, Hadi D Arman, Francis K Yoshimoto. Synthesis of [15,15,15-2H3]-Dihydroartemisinic Acid and Isotope Studies Support a Mixed Mechanism in the Endoperoxide Formation to Artemisinin. Journal of natural products. 2021 07; 84(7):1967-1984. doi: 10.1021/acs.jnatprod.1c00246. [PMID: 34137611]
  • Na Tian, Yuwei Tang, Dongming Tian, Zhonghua Liu, Shuoqian Liu. Determination of dihydroartemisinic acid in Artemisia annua L. by gas chromatography with flame ionization detection. Biomedical chromatography : BMC. 2017 Mar; 31(3):. doi: 10.1002/bmc.3824. [PMID: 27557482]
  • Tomasz Czechowski, Tony R Larson, Theresa M Catania, David Harvey, Geoffrey D Brown, Ian A Graham. Artemisia annua mutant impaired in artemisinin synthesis demonstrates importance of nonenzymatic conversion in terpenoid metabolism. Proceedings of the National Academy of Sciences of the United States of America. 2016 12; 113(52):15150-15155. doi: 10.1073/pnas.1611567113. [PMID: 27930305]
  • Xu Lu, Fangyuan Zhang, Qian Shen, Weimin Jiang, Qifang Pan, Zongyou Lv, Tingxiang Yan, Xueqing Fu, Yuliang Wang, Hongmei Qian, Kexuan Tang. Overexpression of allene oxide cyclase improves the biosynthesis of artemisinin in Artemisia annua L. PloS one. 2014; 9(3):e91741. doi: 10.1371/journal.pone.0091741. [PMID: 24642483]
  • Jianhua Zhu, Jiazeng Yang, Zihan Zeng, Wenjin Zhang, Liyan Song, Wei Wen, Rongmin Yu. Inducing effect of dihydroartemisinic acid in the biosynthesis of artemisinins with cultured cells of Artemisia annua by enhancing the expression of genes. TheScientificWorldJournal. 2014; 2014(?):293190. doi: 10.1155/2014/293190. [PMID: 25136654]
  • John Suberu, Lijiang Song, Susan Slade, Neil Sullivan, Guy Barker, Alexei A Lapkin. A rapid method for the determination of artemisinin and its biosynthetic precursors in Artemisia annua L. crude extracts. Journal of pharmaceutical and biomedical analysis. 2013 Oct; 84(?):269-77. doi: 10.1016/j.jpba.2013.06.025. [PMID: 23867088]
  • Hieng-Ming Ting, Bo Wang, Anna-Margareta Rydén, Lotte Woittiez, Teun van Herpen, Francel W A Verstappen, Carolien Ruyter-Spira, Jules Beekwilder, Harro J Bouwmeester, Alexander van der Krol. The metabolite chemotype of Nicotiana benthamiana transiently expressing artemisinin biosynthetic pathway genes is a function of CYP71AV1 type and relative gene dosage. The New phytologist. 2013 Jul; 199(2):352-366. doi: 10.1111/nph.12274. [PMID: 23638869]
  • Xu Lu, Ling Zhang, Fangyuan Zhang, Weimin Jiang, Qian Shen, Lida Zhang, Zongyou Lv, Guofeng Wang, Kexuan Tang. AaORA, a trichome-specific AP2/ERF transcription factor of Artemisia annua, is a positive regulator in the artemisinin biosynthetic pathway and in disease resistance to Botrytis cinerea. The New phytologist. 2013 Jun; 198(4):1191-1202. doi: 10.1111/nph.12207. [PMID: 23448426]
  • Daniel Kopetzki, François Lévesque, Peter H Seeberger. A continuous-flow process for the synthesis of artemisinin. Chemistry (Weinheim an der Bergstrasse, Germany). 2013 Apr; 19(17):5450-6. doi: 10.1002/chem.201204558. [PMID: 23520059]
  • Patrick J Westfall, Douglas J Pitera, Jacob R Lenihan, Diana Eng, Frank X Woolard, Rika Regentin, Tizita Horning, Hiroko Tsuruta, David J Melis, Andrew Owens, Scott Fickes, Don Diola, Kirsten R Benjamin, Jay D Keasling, Michael D Leavell, Derek J McPhee, Neil S Renninger, Jack D Newman, Chris J Paddon. Production of amorphadiene in yeast, and its conversion to dihydroartemisinic acid, precursor to the antimalarial agent artemisinin. Proceedings of the National Academy of Sciences of the United States of America. 2012 Jan; 109(3):E111-8. doi: 10.1073/pnas.1110740109. [PMID: 22247290]
  • Wei Wu, Man Yuan, Qing Zhang, Yanming Zhu, Li Yong, Wei Wang, Yan Qi, Dianjing Guo. Chemotype-dependent metabolic response to methyl jasmonate elicitation in Artemisia annua. Planta medica. 2011 Jul; 77(10):1048-53. doi: 10.1055/s-0030-1250744. [PMID: 21267809]
  • Jorge F S Ferreira, Devanand L Luthria. Drying affects artemisinin, dihydroartemisinic acid, artemisinic acid, and the antioxidant capacity of Artemisia annua L. leaves. Journal of agricultural and food chemistry. 2010 Feb; 58(3):1691-8. doi: 10.1021/jf903222j. [PMID: 20050663]
  • Abdul Mannan, Chunzhao Liu, Patrick R Arsenault, Melissa J Towler, Dan R Vail, Argelia Lorence, Pamela J Weathers. DMSO triggers the generation of ROS leading to an increase in artemisinin and dihydroartemisinic acid in Artemisia annua shoot cultures. Plant cell reports. 2010 Feb; 29(2):143-52. doi: 10.1007/s00299-009-0807-y. [PMID: 20084379]
  • Gao-Bin Pu, Dong-Ming Ma, Jian-Lin Chen, Lan-Qing Ma, Hong Wang, Guo-Feng Li, He-Chun Ye, Ben-Ye Liu. Salicylic acid activates artemisinin biosynthesis in Artemisia annua L. Plant cell reports. 2009 Jul; 28(7):1127-35. doi: 10.1007/s00299-009-0713-3. [PMID: 19521701]
  • Chenfei Ma, Huahong Wang, Xin Lu, Guowang Xu, Benye Liu. Metabolic fingerprinting investigation of Artemisia annua L. in different stages of development by gas chromatography and gas chromatography-mass spectrometry. Journal of chromatography. A. 2008 Apr; 1186(1-2):412-9. doi: 10.1016/j.chroma.2007.09.023. [PMID: 17915234]
  • Jorge F S Ferreira. Nutrient deficiency in the production of artemisinin, dihydroartemisinic acid, and artemisinic acid in Artemisia annua L. Journal of agricultural and food chemistry. 2007 Mar; 55(5):1686-94. doi: 10.1021/jf063017v. [PMID: 17295513]