0F35AOI227 (BioDeep_00000230160)

Main id: BioDeep_00000014667

 

PANOMIX_OTCML-2023 Chemicals and Drugs


代谢物信息卡片


Furo(3,4:6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5R-(5-alpha,5a-alpha,8a-alpha,9-alpha))-

化学式: C22H22O8 (414.1315)
中文名称: 苦鬼臼毒素, PPP
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: COC1=CC(=CC(=C1OC)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O
InChI: InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19+,20-/m0/s1

描述信息

Picropodophyllotoxin is an organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing 3,4,5-trimethoxyphenyl and hydroxy substituents. It has a role as an antineoplastic agent, a tyrosine kinase inhibitor, an insulin-like growth factor receptor 1 antagonist and a plant metabolite. It is a lignan, a furonaphthodioxole and an organic heterotetracyclic compound.
Picropodophyllin has been investigated for the treatment of Non Small Cell Lung Cancer.
Picropodophyllin is a natural product found in Juniperus, Juniperus thurifera, and other organisms with data available.
Picropodophyllin is a cyclolignan alkaloid found in the mayapple plant family (Podophyllum peltatum), and a small molecule inhibitor of the insulin-like growth factor 1 receptor (IGF1R) with potential antineoplastic activity. Picropodophyllin specifically inhibits the activity and downregulates the cellular expression of IGF1R without interfering with activities of other growth factor receptors, such as receptors for insulin, epidermal growth factor, platelet-derived growth factor, fibroblast growth factor and mast/stem cell growth factor (KIT). This agent shows potent activity in the suppression o f tumor cell proliferation and the induction of tumor cell apoptosis. IGF1R, a receptor tyrosine kinase overexpressed in a variety of human cancers, plays a critical role in the growth and survival of many types of cancer cells.
An organic heterotetracyclic compound that has a furonaphthodioxole skeleton bearing 3,4,5-trimethoxyphenyl and hydroxy substituents.
C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor > C129824 - Antineoplastic Protein Inhibitor
C274 - Antineoplastic Agent > C1931 - Antineoplastic Plant Product > C1331 - Epipodophyllotoxin Compound
C471 - Enzyme Inhibitor > C129825 - Antineoplastic Enzyme Inhibitor > C1748 - Topoisomerase Inhibitor
C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C1967 - Tyrosine Kinase Inhibitor
C1907 - Drug, Natural Product
Picropodophyllin (AXL1717) is a selective insulin-like growth factor-1 receptor (IGF-1R) inhibitor with an IC50 of 1 nM.
Picropodophyllin (AXL1717) is a selective insulin-like growth factor-1 receptor (IGF-1R) inhibitor with an IC50 of 1 nM.

同义名列表

39 个代谢物同义名

Furo(3,4:6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5R-(5-alpha,5a-alpha,8a-alpha,9-alpha))-; Furo[3,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, [5R-(5.alpha.,5a.alpha.,8a.alpha.,9.alpha.)]-; 5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3,4:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, [5R-(.alpha.-5a.alpha.,8a.alpha.,9.alpha.)]; Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5R,5aS,8aR,9R)-; (10R,11S,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1(9),2,7-trien-12-one; (10R,11S,15R,16R)-16-hydroxy-10-(3,4,5-trimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0?,?.0??,??]hexadeca-1(9),2,7-trien-12-one; (5R,5aS,8aR,9R)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-furo[3,4:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one; (5R,5aS,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3,4:6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one; (5R,5aS,8aR,9R)-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3,4:6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one; (5R,5AS,8AR,9R)-9-HYDROXY-5-(3,4,5-TRIMETHOXYPHENYL)-5,5A,8A,9-TETRAHYDROFURO(3,4:6,7)NAPHTHO(2,3-D)(1,3)DIOXOL-6(8H)-ONE; (5R,5aR,8aS,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one; (5R,5aR,8aS,9R)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one; WLN: T E5 C665 FVO NO PO OHTT&&J DR CO1 DO1 EO1& JQ; Picropodophyllotoxin, >=96\\% (HPLC), powder; Picropodophyllotoxin;Picropodophyllin;PPP; PODOPHYLLOTOXIN IMPURITY A [EP IMPURITY]; PODOPHYLLOTOXIN PICROPODOPHYLLIN [MI]; Podophyllotoxin picropodophyllin; YJGVMLPVUAXIQN-HAEOHBJNSA-N; PICROPODOPHYLLIN [WHO-DD]; picropodophyllin (PPP); IGF-1R Inhibitor, PPP; Picropodophyllotoxin; picro-podophyllin; Spectrum4_001836; Picropodophyllin; Spectrum5_000631; Spectrum2_000520; Spectrum3_001671; cyclolignan PPP; UNII-0F35AOI227; KBio2_007252; KBio3_002701; KBio2_004684; KBio2_002116; 0F35AOI227; (-)PPP; AXL1717; Picropodophyllin



数据库引用编号

16 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)

3 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

  • Jing Hu, Jiali Wu, Qihuang Jin, Ling Zhang, Ning Shen, Yiyang Shu, Lu Cheng, Jian Zhang, Guangyi Hu, Kangjia Lv, Qizhi Jian, Hui Chen, Fang Zhang, Xiaodong Sun. Repurposing picropodophyllin as a potential thyroid eye disease treatment via delaying mitotic clonal expansion through a patient-derived preclinical platform. Clinical and translational medicine. 2023 04; 13(4):e1218. doi: 10.1002/ctm2.1218. [PMID: 37012693]
  • Xuejie Zhu, Xiaojie Chen, Guoli Wang, Dan Lei, Xiaoyu Chen, Kehao Lin, Minjing Li, Haiyan Lin, Defang Li, Qiusheng Zheng. Picropodophyllin Inhibits the Proliferation of Human Prostate Cancer DU145 and LNCaP Cells via ROS Production and PI3K/AKT Pathway Inhibition. Biological & pharmaceutical bulletin. 2022; 45(8):1027-1035. doi: 10.1248/bpb.b21-01006. [PMID: 35908886]
  • Xiangxiang Zhou, Na Chen, Hongzhi Xu, Xiaoming Zhou, Jianhong Wang, Xiaosheng Fang, Ya Zhang, Ying Li, Juan Yang, Xin Wang. Regulation of Hippo-YAP signaling by insulin-like growth factor-1 receptor in the tumorigenesis of diffuse large B-cell lymphoma. Journal of hematology & oncology. 2020 06; 13(1):77. doi: 10.1186/s13045-020-00906-1. [PMID: 32546241]
  • Qi Zhang, Jing Pan, Ronald A Lubet, Yian Wang, Ming You. Targeting the insulin-like growth factor-1 receptor by picropodophyllin for lung cancer chemoprevention. Molecular carcinogenesis. 2015 Jun; 54 Suppl 1(?):E129-37. doi: 10.1002/mc.22206. [PMID: 25163779]
  • Chia-Wen Hsu, Jinghua Zhao, Ruili Huang, Jui-Hua Hsieh, Jon Hamm, Xiaoqing Chang, Keith Houck, Menghang Xia. Quantitative high-throughput profiling of environmental chemicals and drugs that modulate farnesoid X receptor. Scientific reports. 2014 Sep; 4(?):6437. doi: 10.1038/srep06437. [PMID: 25257666]
  • K Fujiki, H Inamura, M Matsuoka. Detrimental effects of Notch1 signaling activated by cadmium in renal proximal tubular epithelial cells. Cell death & disease. 2014 Aug; 5(?):e1378. doi: 10.1038/cddis.2014.339. [PMID: 25118938]
  • Kota Fujiki, Hisako Inamura, Masato Matsuoka. Phosphorylation of FOXO3a by PI3K/Akt pathway in HK-2 renal proximal tubular epithelial cells exposed to cadmium. Archives of toxicology. 2013 Dec; 87(12):2119-27. doi: 10.1007/s00204-013-1077-6. [PMID: 23673518]
  • Deeksha Vishwamitra, Ping Shi, Desiree Wilson, Roxsan Manshouri, Francisco Vega, Ellen J Schlette, Hesham M Amin. Expression and effects of inhibition of type I insulin-like growth factor receptor tyrosine kinase in mantle cell lymphoma. Haematologica. 2011 Jun; 96(6):871-80. doi: 10.3324/haematol.2010.031567. [PMID: 21330319]
  • Mayumi Miura, Mika Sasaki, Keiko Mizukoshi, Masayuki Shibasaki, Yuta Izumi, Goshun Shimosato, Fumimasa Amaya. Peripheral sensitization caused by insulin-like growth factor 1 contributes to pain hypersensitivity after tissue injury. Pain. 2011 Apr; 152(4):888-895. doi: 10.1016/j.pain.2011.01.004. [PMID: 21296499]
  • Yuko Rönquist-Nii, Staffan Eksborg, Magnus Axelson, Johan Harmenberg, Simon Ekman, Michael Bergqvist, Olof Beck. Determination of picropodophyllin and its isomer podophyllotoxin in human serum samples with electrospray ionization of hexylamine adducts by liquid chromatography-tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2011 Feb; 879(5-6):326-34. doi: 10.1016/j.jchromb.2010.12.017. [PMID: 21251888]
  • Chiara Ristori, Luca Filippi, Massimo Dal Monte, Davide Martini, Maurizio Cammalleri, Pina Fortunato, Giancarlo la Marca, Patrizio Fiorini, Paola Bagnoli. Role of the adrenergic system in a mouse model of oxygen-induced retinopathy: antiangiogenic effects of beta-adrenoreceptor blockade. Investigative ophthalmology & visual science. 2011 Jan; 52(1):155-70. doi: 10.1167/iovs.10-5536. [PMID: 20739470]
  • Mario-Alexander Economou. Uveal melanoma and macular degeneration: molecular biology and potential therapeutic applications. Acta ophthalmologica. 2008 Dec; 86(8):930-1. doi: 10.1111/j.1755-3768.2008.01188.x. [PMID: 19086934]
  • Helena Jernberg-Wiklund, Kenneth Nilsson. Control of apoptosis in human multiple myeloma by insulin-like growth factor I (IGF-I). Advances in cancer research. 2007; 97(?):139-65. doi: 10.1016/s0065-230x(06)97006-7. [PMID: 17419944]
  • Eline Menu, Helena Jernberg-Wiklund, Thomas Stromberg, Hendrik De Raeve, Leonard Girnita, Olle Larsson, Magnus Axelson, Kewal Asosingh, Kenneth Nilsson, Ben Van Camp, Karin Vanderkerken. Inhibiting the IGF-1 receptor tyrosine kinase with the cyclolignan PPP: an in vitro and in vivo study in the 5T33MM mouse model. Blood. 2006 Jan; 107(2):655-60. doi: 10.1182/blood-2005-01-0293. [PMID: 16046527]
  • E Bedows, G M Hatfield. An investigation of the antiviral activity of Podophyllum peltatum. Journal of natural products. 1982 Nov; 45(6):725-9. doi: 10.1021/np50024a015. [PMID: 6298369]