5,8-Dihydroxy-1,4-naphthoquinone (BioDeep_00000181552)

   

human metabolite blood metabolite natural product


代谢物信息卡片


5,8-dihydroxy-1,4-dihydronaphthalene-1,4-dione

化学式: C10H6O4 (190.0266)
中文名称: 5,8-二羟基-1,4-萘醌
谱图信息: 最多检出来源 Homo sapiens(blood) 91.67%

分子结构信息

SMILES: C1=CC(=C2C(=O)C=CC(=O)C2=C1O)O
InChI: InChI=1S/C10H6O4/c11-5-1-2-6(12)10-8(14)4-3-7(13)9(5)10/h1-4,11-12H

描述信息

D000970 - Antineoplastic Agents

同义名列表

10 个代谢物同义名

5,8-dihydroxy-1,4-dihydronaphthalene-1,4-dione; 5,8-Dihydroxy-1,4-naphthosemiquinone; 5,8-Dihydroxy-1,4-naphthalenedione; 5,8-Dihydroxy-1,4-naphthoquinone; 5,8-Dioxy-1,4-naphthoquinone; 5,8-Dihydroxynaphthoquinone; Naphthazarone; Naphthazarine; Naphthazarin; Naphthazarin



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)

8 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 12 ANXA5, BAX, CASP3, CAT, CDC25C, HDAC1, HPGDS, NQO1, PIK3CA, PMP2, SRARP, TGFB1
Peripheral membrane protein 1 ANXA5
Endosome membrane 1 CTSD
Endoplasmic reticulum membrane 1 BAX
Nucleus 13 BAX, CASP3, CDC25C, DNMT1, GABPA, HDAC1, NQO1, PARP1, PMP2, SRARP, TGFB1, TOP1, UHRF1
cytosol 12 ANXA5, BAX, CASP3, CAT, CDC25C, EHHADH, HDAC1, HPGDS, NQO1, PARP1, PIK3CA, PMP2
dendrite 1 NQO1
nuclear body 1 PARP1
nucleoplasm 9 CASP3, CDC25C, DNMT1, GABPA, HDAC1, HPGDS, PARP1, TOP1, UHRF1
lamellipodium 1 PIK3CA
Synapse 1 NQO1
cell surface 1 TGFB1
glutamatergic synapse 1 CASP3
lysosomal membrane 1 CTSD
neuronal cell body 4 CASP3, HDAC1, NQO1, TGFB1
sarcolemma 1 ANXA5
Cytoplasm, cytosol 2 NQO1, PARP1
Lysosome 1 CTSD
plasma membrane 2 PIK3CA, TGFB1
Membrane 5 ANXA5, BAX, CAT, NQO1, PARP1
axon 1 TGFB1
extracellular exosome 5 ANXA5, BAX, CAT, CTSD, PMP2
endoplasmic reticulum 1 BAX
extracellular space 2 CTSD, TGFB1
lysosomal lumen 1 CTSD
perinuclear region of cytoplasm 2 CDC25C, PIK3CA
intercalated disc 1 PIK3CA
mitochondrion 4 BAX, CAT, DNMT1, PARP1
protein-containing complex 3 CAT, HDAC1, PARP1
intracellular membrane-bounded organelle 2 CAT, HPGDS
postsynaptic density 1 CASP3
pericentric heterochromatin 1 DNMT1
Secreted 1 TGFB1
extracellular region 4 ANXA5, CAT, CTSD, TGFB1
Single-pass membrane protein 1 BAX
mitochondrial outer membrane 1 BAX
mitochondrial matrix 1 CAT
transcription regulator complex 1 PARP1
BAK complex 1 BAX
Bcl-2 family protein complex 1 BAX
external side of plasma membrane 1 ANXA5
Secreted, extracellular space, extracellular matrix 1 TGFB1
perikaryon 1 TOP1
nucleolus 2 PARP1, TOP1
P-body 1 TOP1
heterochromatin 2 HDAC1, UHRF1
Membrane raft 1 CTSD
pore complex 1 BAX
focal adhesion 2 ANXA5, CAT
spindle 1 UHRF1
extracellular matrix 1 TGFB1
Peroxisome 2 CAT, EHHADH
Peroxisome matrix 1 CAT
peroxisomal matrix 2 CAT, EHHADH
peroxisomal membrane 1 CAT
mitochondrial intermembrane space 1 CDC25C
collagen-containing extracellular matrix 3 ANXA5, CTSD, TGFB1
secretory granule 1 TGFB1
Zymogen granule membrane 1 ANXA5
chromatin 4 GABPA, HDAC1, PARP1, UHRF1
Chromosome 2 PARP1, TOP1
Nucleus, nucleolus 2 PARP1, TOP1
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
blood microparticle 1 TGFB1
site of double-strand break 1 PARP1
fibrillar center 1 TOP1
nuclear envelope 2 BAX, PARP1
endosome lumen 1 CTSD
female germ cell nucleus 1 DNMT1
Nucleus, nucleoplasm 1 TOP1
Melanosome 1 CTSD
euchromatin 1 UHRF1
replication fork 2 DNMT1, UHRF1
myelin sheath 1 PMP2
ficolin-1-rich granule lumen 2 CAT, CTSD
secretory granule lumen 1 CAT
Golgi lumen 1 TGFB1
nuclear matrix 1 UHRF1
transcription repressor complex 1 HDAC1
male germ cell nucleus 1 TOP1
platelet alpha granule lumen 1 TGFB1
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
specific granule lumen 1 CTSD
tertiary granule lumen 1 CTSD
histone deacetylase complex 1 HDAC1
NuRD complex 1 HDAC1
vesicle membrane 1 ANXA5
Sin3-type complex 1 HDAC1
protein-DNA complex 2 PARP1, TOP1
death-inducing signaling complex 1 CASP3
site of DNA damage 1 PARP1
[Latency-associated peptide]: Secreted, extracellular space, extracellular matrix 1 TGFB1
[Transforming growth factor beta-1]: Secreted 1 TGFB1
catalase complex 1 CAT
mitochondrial permeability transition pore complex 1 BAX
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
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[Isoform Alpha]: Mitochondrion outer membrane 1 BAX
[Isoform Delta]: Cytoplasm 1 BAX
BAX complex 1 BAX


文献列表

  • Muhammad Furqan, Alishba Fayyaz, Farhat Firdous, Hadeeqa Raza, Aishah Bilal, Rahman Shah Zaib Saleem, Syed Shahzad-Ul-Hussan, Daijie Wang, Fadia S Youssef, Nawal M Al Musayeib, Mohamed L Ashour, Hidayat Hussain, Amir Faisal. Identification and Characterization of Natural and Semisynthetic Quinones as Aurora Kinase Inhibitors. Journal of natural products. 2022 06; 85(6):1503-1513. doi: 10.1021/acs.jnatprod.1c01222. [PMID: 35687347]
  • Lynda Bouarab, Pascal Degraeve, Jalloul Bouajila, Amandine Cottaz, Fouzia Jbilou, Catherine Joly, Nadia Oulahal. Staphylococcus aureus membrane-damaging activities of four phenolics. FEMS microbiology letters. 2021 07; 368(13):. doi: 10.1093/femsle/fnab081. [PMID: 34173656]
  • Nidhi Sharma, Ashu Gulati. Selective binding of Ni2+ and Cu2+ metal ions with naphthazarin esters isolated from Arnebia euchroma. Biotechnology progress. 2020 07; 36(4):e2985. doi: 10.1002/btpr.2985. [PMID: 32103632]
  • Małgorzata Rudnicka, Michał Ludynia, Waldemar Karcz. Effects of Naphthazarin (DHNQ) Combined with Lawsone (NQ-2-OH) or 1,4-Naphthoquinone (NQ) on the Auxin-Induced Growth of Zea mays L. Coleoptile Segments. International journal of molecular sciences. 2019 Apr; 20(7):. doi: 10.3390/ijms20071788. [PMID: 30978914]
  • Prashant Joshi, Vinay R Sonawane, Ibidapo S Williams, Glen J P McCann, Linda Gatchie, Rajni Sharma, Naresh Satti, Bhabatosh Chaudhuri, Sandip B Bharate. Identification of karanjin isolated from the Indian beech tree as a potent CYP1 enzyme inhibitor with cellular efficacy via screening of a natural product repository. MedChemComm. 2018 Feb; 9(2):371-382. doi: 10.1039/c7md00388a. [PMID: 30108931]
  • Chang Su, Dongjian Zhang, Na Bao, Aiyan Ji, Yuanbo Feng, Li Chen, Yicheng Ni, Jian Zhang, Zhiqi Yin. Evaluation of Radioiodinated 1,4-Naphthoquinones as Necrosis Avid Agents for Rapid Myocardium Necrosis Imaging. Molecular imaging and biology. 2018 02; 20(1):74-84. doi: 10.1007/s11307-017-1089-3. [PMID: 28470585]
  • Zhi Sun, Longshan Zhao, Lihua Zuo, Chao Qi, Pan Zhao, Xiaohong Hou. A UHPLC-MS/MS method for simultaneous determination of six flavonoids, gallic acid and 5,8-dihydroxy-1,4-naphthoquinone in rat plasma and its application to a pharmacokinetic study of Cortex Juglandis Mandshuricae extract. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 May; 958(?):55-62. doi: 10.1016/j.jchromb.2014.03.013. [PMID: 24704688]
  • Thilo Christopher Fischer, Christian Gosch, Beate Mirbeth, Markus Gselmann, Veronika Thallmair, Karl Stich. Potent and specific bactericidal effect of juglone (5-hydroxy-1,4-naphthoquinone) on the fire blight pathogen Erwinia amylovora. Journal of agricultural and food chemistry. 2012 Dec; 60(49):12074-81. doi: 10.1021/jf303584r. [PMID: 23163769]
  • Gulseren Pekin, Markus Ganzera, Serdar Senol, Erdal Bedir, Kemal S Korkmaz, Hermann Stuppner. Determination of naphthazarin derivatives in endemic Turkish Alkanna species by reversed phase high performance liquid chromatography. Planta medica. 2007 Mar; 73(3):267-72. doi: 10.1055/s-2007-967110. [PMID: 17318780]
  • Tatjana Kundaković, Tatjana Stanojković, Zorica Juranić, Nada Kovacević. Cytotoxicity in vitro of naphthazarin derivatives from Onosma arenaria. Phytotherapy research : PTR. 2006 Jul; 20(7):602-4. doi: 10.1002/ptr.1899. [PMID: 16718737]
  • Byeoung-Soo Park, Hyun-Kyung Lee, Sung-Eun Lee, Xiang-Lan Piao, Gary R Takeoka, Rosalind Y Wong, Young-Joon Ahn, Jeong-Han Kim. Antibacterial activity of Tabebuia impetiginosa Martius ex DC (Taheebo) against Helicobacter pylori. Journal of ethnopharmacology. 2006 Apr; 105(1-2):255-62. doi: 10.1016/j.jep.2005.11.005. [PMID: 16359837]
  • Ihsan Ergün, M Cenk Akbostanci, Başol Canbakan, Bilge Koçer, Arzu Ensari, Gökhan Nergizoglu, Kenan Keven. Minimal change nephrotic syndrome with stiff-person syndrome: is there a link?. American journal of kidney diseases : the official journal of the National Kidney Foundation. 2005 Jul; 46(1):e11-4. doi: 10.1053/j.ajkd.2005.03.009. [PMID: 15983949]
  • Luis F C Medina, Valter Stefani, Adriano Brandelli. Use of 1,4-naphthoquinones for control of Erwinia carotovora. Canadian journal of microbiology. 2004 Nov; 50(11):951-6. doi: 10.1139/w04-088. [PMID: 15644912]
  • Alois A Bell, Michael H Wheeler, Jinggao Liu, Robert D Stipanovic, Lorraine S Puckhaber, Heather Orta. United States Department of Agriculture-Agricultural Research Service studies on polyketide toxins of Fusarium oxysporum f sp vasinfectum: potential targets for disease control. Pest management science. 2003 Jun; 59(6-7):736-47. doi: 10.1002/ps.713. [PMID: 12846324]
  • Nikolaos K Andrikopoulos, Andriana C Kaliora, Andreana N Assimopoulou, Vassilios P Papapeorgiou. Biological activity of some naturally occurring resins, gums and pigments against in vitro LDL oxidation. Phytotherapy research : PTR. 2003 May; 17(5):501-7. doi: 10.1002/ptr.1185. [PMID: 12748987]
  • Angeliki P Kourounakis, Andreana N Assimopoulou, Vassilios P Papageorgiou, Antonis Gavalas, Panos N Kourounakis. Alkannin and shikonin: effect on free radical processes and on inflammation - a preliminary pharmacochemical investigation. Archiv der Pharmazie. 2002 Jun; 335(6):262-6. doi: 10.1002/1521-4184(200208)335:6<262::aid-ardp262>3.0.co;2-y. [PMID: 12210768]
  • D Gao, M Kakuma, S Oka, K Sugino, H Sakurai. Reaction of beta-alkannin (shikonin) with reactive oxygen species: detection of beta-alkannin free radicals. Bioorganic & medicinal chemistry. 2000 Nov; 8(11):2561-9. doi: 10.1016/s0968-0896(00)00191-7. [PMID: 11092541]
  • K Roberg, K Ollinger. Oxidative stress causes relocation of the lysosomal enzyme cathepsin D with ensuing apoptosis in neonatal rat cardiomyocytes. The American journal of pathology. 1998 May; 152(5):1151-6. doi: . [PMID: 9588882]
  • K Ollinger, U T Brunk. Cellular injury induced by oxidative stress is mediated through lysosomal damage. Free radical biology & medicine. 1995 Nov; 19(5):565-74. doi: 10.1016/0891-5849(95)00062-3. [PMID: 8529915]
  • A Nemeikaite, N Cenas. The changes of prooxidant and antioxidant enzyme activities in bovine leukemia virus-transformed cells. Their influence on quinone cytotoxicity. FEBS letters. 1993 Jul; 326(1-3):65-8. doi: 10.1016/0014-5793(93)81762-o. [PMID: 8392004]
  • M Nozaki. [Combined use of bucolome and pyrazolone derivatives (1). Pharmacological activities and blood concentration]. Nihon yakurigaku zasshi. Folia pharmacologica Japonica. 1975 Sep; 71(6):609-29. doi: NULL. [PMID: 281]