Miltirone (BioDeep_00000003661)

 

Secondary id: BioDeep_00000402775

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


miltirone;2-Isopropyl-8,8-dimethyl-5,6,7,8-tetrahydro-phenanthrene-3,4-dione

化学式: C19H22O2 (282.162)
中文名称: 新丹参酮, 丹参新酮, 次丹参醌, 米替隆
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 45.88%

分子结构信息

SMILES: CC(C)C1=CC2=C(C(=O)C1=O)C1=C(C=C2)C(C)(C)CCC1
InChI: InChI=1S/C19H22O2/c1-11(2)14-10-12-7-8-15-13(6-5-9-19(15,3)4)16(12)18(21)17(14)20/h7-8,10-11H,5-6,9H2,1-4H3

描述信息

Constituent of roots of Salvia miltiorrhiza (Chinese sage)and is) also present in leaves of rosemary (Rosmarinus officinalis). Antioxidant. Miltirone is found in herbs and spices, rosemary, and common sage.
Miltirone is found in common sage. Miltirone is a constituent of roots of Salvia miltiorrhiza (Chinese sage). Also present in leaves of rosemary (Rosmarinus officinalis). Antioxidant
Miltirone is an abietane diterpenoid.
Miltirone is a natural product found in Salvia, Salvia miltiorrhiza, and other organisms with data available.
Miltirone is a natural compound present in the root of Salvia miltiorrhiza. Miltirone is a central benzodiazepine receptor partial agonist, with an IC50 of 0.3 μM[1].
Miltirone is a natural compound present in the root of Salvia miltiorrhiza. Miltirone is a central benzodiazepine receptor partial agonist, with an IC50 of 0.3 μM[1].
Miltirone is a natural compound present in the root of Salvia miltiorrhiza. Miltirone is a central benzodiazepine receptor partial agonist, with an IC50 of 0.3 μM[1].

同义名列表

19 个代谢物同义名

miltirone;2-Isopropyl-8,8-dimethyl-5,6,7,8-tetrahydro-phenanthrene-3,4-dione; 5,6,7,8-Tetrahydro-8,8-dimethyl-2-(1-methylethyl)-3,4-phenanthrenedione, 9CI; 3,4-Phenanthrenedione, 5,6,7,8-tetrahydro-8,8-dimethyl-2-(1-methylethyl)-; 8,8-dimethyl-2-(propan-2-yl)-3,4,5,6,7,8-hexahydrophenanthrene-3,4-dione; 5,6,7,8-Tetrahydro-8,8-dimethyl-2-(1-methylethyl)-3,4-phenanthrenedione; 5,6,7,8-tetrahydro-8,8-dimethyl-2-isopropyl-3,4-phenanthrenedione; 2-Isopropyl-8,8-dimethyl-5,6,7,8-tetrahydro-3,4-phenanthrenedione; 2-isopropyl-8,8-dimethyl-5,6,7,8-tetrahydrophenanthrene-3,4-dione; 5,6,7,8-Tetrahydro-2-isopropyl-8,8-dimethyl-3,4-phenanthraquinone; 8,8-dimethyl-2-propan-2-yl-6,7-dihydro-5H-phenanthrene-3,4-dione; 2-isopropyl-8,8-dimethyl-6,7-dihydro-5H-phenanthrene-3,4-dione; 20-Nor-5,7,9,13-abietatetraene-11,12-dione; FEFAIBOZOKSLJR-UHFFFAOYSA-N; Rosmariquinone; NCI60_013161; Miltirone; Miltrione; Miltiron; Miltirone



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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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)

27 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 14 ANXA5, BCL2, CASP12, CASP3, CASP8, CCNB1, GSDME, MAPK8, MYD88, NCOA2, NQO1, PIK3CA, RELA, TP53
Peripheral membrane protein 2 ANXA5, CYP1B1
Endosome membrane 1 MYD88
Endoplasmic reticulum membrane 2 BCL2, CYP1B1
Nucleus 12 BCL2, CASP3, CASP8, CCNB1, MAPK8, MMP2, MYD88, NCOA2, NQO1, PARP1, RELA, TP53
cytosol 13 ANXA5, BCL2, CASP3, CASP8, CCNB1, GSDME, MAPK8, MYD88, NQO1, PARP1, PIK3CA, RELA, TP53
dendrite 1 NQO1
nuclear body 2 NCOA2, PARP1
centrosome 2 CCNB1, TP53
nucleoplasm 8 CASP3, CASP8, CCNB1, MAPK8, NCOA2, PARP1, RELA, TP53
RNA polymerase II transcription regulator complex 1 NCOA2
Cell membrane 2 GSDME, TNF
lamellipodium 2 CASP8, PIK3CA
Multi-pass membrane protein 1 GSDME
Synapse 2 MAPK8, NQO1
cell surface 2 MYD88, TNF
glutamatergic synapse 2 CASP3, RELA
neuronal cell body 3 CASP3, NQO1, TNF
sarcolemma 1 ANXA5
Cytoplasm, cytosol 2 NQO1, PARP1
plasma membrane 5 GSDME, MMP2, MYD88, PIK3CA, TNF
Membrane 8 ANXA5, BCL2, CCNB1, CYP1B1, GSDME, NQO1, PARP1, TP53
axon 2 CCK, MAPK8
extracellular exosome 2 ANXA5, MMP9
endoplasmic reticulum 3 BCL2, CASP12, TP53
extracellular space 4 CCK, MMP2, MMP9, TNF
perinuclear region of cytoplasm 1 PIK3CA
intercalated disc 1 PIK3CA
mitochondrion 6 BCL2, CASP8, CYP1B1, MMP2, PARP1, TP53
protein-containing complex 6 BCL2, CASP8, MYD88, NCOA2, PARP1, TP53
intracellular membrane-bounded organelle 1 CYP1B1
Microsome membrane 1 CYP1B1
postsynaptic density 1 CASP3
Secreted 1 CCK
extracellular region 5 ANXA5, CCK, MMP2, MMP9, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 2 BCL2, CASP8
Mitochondrion matrix 1 TP53
mitochondrial matrix 2 CCNB1, TP53
transcription regulator complex 4 NCOA2, PARP1, RELA, TP53
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 TP53
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 2 ANXA5, TNF
Secreted, extracellular space, extracellular matrix 1 MMP9
nucleolus 2 PARP1, TP53
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Cell projection, lamellipodium 1 CASP8
Membrane raft 1 TNF
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 TP53
focal adhesion 1 ANXA5
extracellular matrix 1 MMP2
Nucleus, PML body 1 TP53
PML body 1 TP53
collagen-containing extracellular matrix 3 ANXA5, MMP2, MMP9
sarcomere 1 MMP2
Zymogen granule membrane 1 ANXA5
chromatin 4 NCOA2, PARP1, RELA, TP53
phagocytic cup 1 TNF
Chromosome 1 PARP1
cytoskeleton 1 CASP8
Nucleus, nucleolus 1 PARP1
spindle pole 1 CCNB1
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
site of double-strand break 2 PARP1, TP53
nuclear envelope 1 PARP1
cell body 1 CASP8
germ cell nucleus 1 TP53
replication fork 1 TP53
myelin sheath 1 BCL2
ficolin-1-rich granule lumen 1 MMP9
nuclear matrix 1 TP53
transcription repressor complex 1 TP53
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
tertiary granule lumen 1 MMP9
[Isoform 1]: Secreted, extracellular space, extracellular matrix 1 MMP2
outer kinetochore 1 CCNB1
vesicle membrane 1 ANXA5
[Isoform 1]: Nucleus 1 TP53
extrinsic component of cytoplasmic side of plasma membrane 1 MYD88
protein-DNA complex 1 PARP1
basal dendrite 1 MAPK8
CD95 death-inducing signaling complex 1 CASP8
death-inducing signaling complex 2 CASP3, CASP8
ripoptosome 1 CASP8
[Gasdermin-E, N-terminal]: Cell membrane 1 GSDME
[Gasdermin-E]: Cytoplasm, cytosol 1 GSDME
extrinsic component of plasma membrane 1 MYD88
site of DNA damage 1 PARP1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
cyclin B1-CDK1 complex 1 CCNB1
endothelial microparticle 1 ANXA5
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
BAD-BCL-2 complex 1 BCL2
NF-kappaB p50/p65 complex 1 RELA
NF-kappaB complex 1 RELA
NLRP1 inflammasome complex 1 CASP12
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Shan-Shan Chen, Hua-Su Zhu, Na Dong, Ya-Ping Zhang, Min Wu, Ling-Hong Liu, Qing Shi, Dong Li, Xiu-Li Ju. [Effect of miltirone on proliferation and apoptosis of leukemia THP-1 cells]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2022 May; 47(9):2541-2546. doi: 10.19540/j.cnki.cjcmm.20211206.701. [PMID: 35531702]
  • Mei-Ting Liu, Jing Zhao, Shao-Ping Li. Application of smartphone in detection of thin-layer chromatography: Case of salvia miltiorrhiza. Journal of chromatography. A. 2021 Jan; 1637(?):461826. doi: 10.1016/j.chroma.2020.461826. [PMID: 33387914]
  • Lijun Ni, Fangfang Zhang, Mingyue Han, Liguo Zhang, Shaorong Luan, Wei Li, Haixing Deng, Zhuhui Lan, Zhongxiang Wu, Xiaofang Luo, Leslaw Mleczko. Qualitative analysis of the roots of Salvia miltiorrhiza and Salvia yunnanensis based on NIR, UHPLC and LC-MS-MS. Journal of pharmaceutical and biomedical analysis. 2019 Jun; 170(?):295-304. doi: 10.1016/j.jpba.2019.01.010. [PMID: 30951995]
  • F Sezer Senol, Sylwester Ślusarczyk, Adam Matkowski, Alfonso Pérez-Garrido, Francisco Girón-Rodríguez, José P Cerón-Carrasco, Helena den-Haan, Jorge Peña-García, Horacio Pérez-Sánchez, Krzysztof Domaradzki, Ilkay Erdogan Orhan. Selective in vitro and in silico butyrylcholinesterase inhibitory activity of diterpenes and rosmarinic acid isolated from Perovskia atriplicifolia Benth. and Salvia glutinosa L. Phytochemistry. 2017 Jan; 133(?):33-44. doi: 10.1016/j.phytochem.2016.10.012. [PMID: 27817931]
  • Hongjian Wang, Junfei Gu, Xuefeng Hou, Juan Chen, Nan Yang, Ying Liu, Gang Wang, Mei Du, Huihui Qiu, Yi Luo, Ziyu Jiang, Liang Feng. Anti-inflammatory effect of miltirone on inflammatory bowel disease via TLR4/NF-κB/IQGAP2 signaling pathway. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2017 Jan; 85(?):531-540. doi: 10.1016/j.biopha.2016.11.061. [PMID: 27903427]
  • Liu Zhang, Hui Zhang, Xueyan Li, Bingjie Jia, Yuyu Yang, Ping Zhou, Ping Li, Jun Chen. Miltirone protects human EA.hy926 endothelial cells from oxidized low-density lipoprotein-derived oxidative stress via a heme oxygenase-1 and MAPK/Nrf2 dependent pathway. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2016 Dec; 23(14):1806-1813. doi: 10.1016/j.phymed.2016.11.003. [PMID: 27912883]
  • Hua Yang, Yao Ding, Wen Gao, Lian-Wen Qi, Jun Cao, Ping Li. Efficient separation of tanshinones by polyvinylpyrrolidone-stabilized graphene-modified micellar electrokinetic chromatography. Electrophoresis. 2015 Dec; 36(23):2874-80. doi: 10.1002/elps.201500264. [PMID: 26331266]
  • Xuelin Zhou, Yan Wang, Wayne Y W Lee, Penelope M Y Or, David C C Wan, Yiu Wa Kwan, John H K Yeung. Miltirone Is a Dual Inhibitor of P-Glycoprotein and Cell Growth in Doxorubicin-Resistant HepG2 Cells. Journal of natural products. 2015 Sep; 78(9):2266-75. doi: 10.1021/acs.jnatprod.5b00516. [PMID: 26339922]
  • Sylwester Slusarczyk, Jakub Topolski, Krzysztof Domaradzki, Michael Adams, Matthias Hamburger, Adam Matkowski. Isolation and Fast Selective Determination of Nor-abietanoid Diterpenoids from Perovskia atriplicifolia Roots Using LC-ESI-MS/MS with Multiple Reaction Monitoring. Natural product communications. 2015 Jul; 10(7):1149-52. doi: . [PMID: 26410997]
  • Long Guo, Li Duan, Xin Dong, Li-Li Dou, Ping Zhou, Ping Li, E-Hu Liu. Metabolic profile of miltirone in rats by high performance liquid chromatography/quadrupole time-of-flight mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2015 Mar; 107(?):473-9. doi: 10.1016/j.jpba.2015.01.043. [PMID: 25679091]
  • M Jason Hatfield, Lyudmila G Tsurkan, Janice L Hyatt, Carol C Edwards, Andrew Lemoff, Cynthia Jeffries, Bing Yan, Philip M Potter. Modulation of esterified drug metabolism by tanshinones from Salvia miltiorrhiza ('Danshen'). Journal of natural products. 2013 Jan; 76(1):36-44. doi: 10.1021/np300628a. [PMID: 23286284]
  • M Fronza, R Murillo, S Ślusarczyk, M Adams, M Hamburger, B Heinzmann, S Laufer, I Merfort. In vitro cytotoxic activity of abietane diterpenes from Peltodon longipes as well as Salvia miltiorrhiza and Salvia sahendica. Bioorganic & medicinal chemistry. 2011 Aug; 19(16):4876-81. doi: 10.1016/j.bmc.2011.06.067. [PMID: 21775156]
  • Li-Xin Yang, Xing-Cui Li, Chao Liu, Lei Xiao, De-Hua Qin, Ruo-Yun Chen. [Chemical constituents from Salvia przewalskii Maxim]. Yao xue xue bao = Acta pharmaceutica Sinica. 2011 Jul; 46(7):818-21. doi: . [PMID: 22010351]
  • Giancarlo Colombo, Salvatore Serra, Giovanni Vacca, Alessandro Orrù, Paola Maccioni, Paolo Morazzoni, Ezio Bombardelli, Antonella Riva, Gian Luigi Gessa, Mauro A M Carai. Identification of miltirone as active ingredient of Salvia miltiorrhiza responsible for the reducing effect of root extracts on alcohol intake in rats. Alcoholism, clinical and experimental research. 2006 May; 30(5):754-62. doi: 10.1111/j.1530-0277.2006.00088.x. [PMID: 16634843]