1,4-Naphthoquinone (BioDeep_00000000301)
Secondary id: BioDeep_00000017294
human metabolite blood metabolite PANOMIX_OTCML-2023
代谢物信息卡片
1,4-Dihydro-1,4-diketonaphthalene
化学式: C10H6O2 (158.0368)
中文名称: 1,4-萘醌
谱图信息:
最多检出来源 Homo sapiens(blood) 18.45%
分子结构信息
SMILES: C1=CC=C2C(=O)C=CC(=O)C2=C1
InChI: InChI=1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H
描述信息
1,4-naphtoquinone, also known as 1,4-naphthalenedione or 1,4-dihydro-1,4-diketonaphthalene, is a member of the class of compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). 1,4-naphtoquinone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 1,4-naphtoquinone can be synthesized from naphthalene. 1,4-naphtoquinone is also a parent compound for other transformation products, including but not limited to, 2,3-dimethoxynaphthalene-1,4-dione, alisiaquinone A, and 1,4-naphthoquinone-2-carboxylic acid. 1,4-naphtoquinone can be found in liquor, which makes 1,4-naphtoquinone a potential biomarker for the consumption of this food product. 1,4-naphtoquinone is a non-carcinogenic (not listed by IARC) potentially toxic compound.
CONFIDENCE standard compound; INTERNAL_ID 18
1,4-Naphthoquinone is a potential pharmacophore for inhibition of both MAO (monoamine oxidase) and DNA topoisomerase activities, this latter associated with antitumor activity[1].
同义名列表
15 个代谢物同义名
1,4-Dihydro-1,4-diketonaphthalene; 1,4-dihydronaphthalene-1,4-dione; 1,4-naphthalene-dione; 1,4-Naphthalenedione; alpha-Naphthoquinone; 1,4-Naphthoquinone; [1,4]Naphthoquinon; 1,4-naphtoquinone; Α-naphthoquinone; a-naphthoquinone; p-Naphthoquinone; NAPHTHOQUINONE; Succivil; 1,4-NQ; 1,4-Naphthoquinone
数据库引用编号
22 个数据库交叉引用编号
- ChEBI: CHEBI:27418
- KEGG: C02617
- KEGGdrug: D70977
- PubChem: 8530
- HMDB: HMDB0244221
- Metlin: METLIN65798
- ChEMBL: CHEMBL55934
- MetaCyc: CPD0-954
- foodb: FDB000340
- chemspider: 8215
- CAS: 130-15-4
- MoNA: UA001803
- MoNA: UA001805
- PMhub: MS000010698
- PubChem: 5602
- NIKKAJI: J5.430E
- RefMet: Naphthoquinone
- medchemexpress: HY-W015490
- KNApSAcK: 27418
- HERB: HBIN001534
- LOTUS: LTS0176662
- wikidata: Q161542
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
2 个相关的代谢反应过程信息。
Reactome(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(1)
- juglone biosynthesis:
1,4-dihydroxy-2-naphthoate + A + H+ ⟶ 1,4-naphthoquinone + A(H2) + CO2
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
4 个相关的物种来源信息
- 9606 - Homo sapiens: -
- 16719 - Juglans nigra: 10.1016/S0031-9422(00)98092-0
- 51240 - Juglans regia:
- 141191 - Lawsonia inermis: -
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
- Yukie Akutsu, Takaaki Fujiwara, Rintaro Suzuki, Yuki Nishigaya, Toshimasa Yamazaki. Juglone, a plant-derived 1,4-naphthoquinone, binds to hydroxylamine oxidoreductase and inhibits the electron transfer to cytochrome c554.
Applied and environmental microbiology.
2023 Dec; 89(12):e0129123. doi:
10.1128/aem.01291-23. [PMID: 38009977] - Tatyana N Goleva, Konstantin G Lyamzaev, Anton G Rogov, Ljudmila S Khailova, Khoren K Epremyan, Galina P Shumakovich, Lidia V Domnina, Olga Yu Ivanova, Natalia V Marmiy, Tatiana V Zinevich, Dmitry S Esipov, Renata A Zvyagilskaya, Vladimir P Skulachev, Boris V Chernyak. Mitochondria-targeted 1,4-naphthoquinone (SkQN) is a powerful prooxidant and cytotoxic agent.
Biochimica et biophysica acta. Bioenergetics.
2020 08; 1861(8):148210. doi:
10.1016/j.bbabio.2020.148210. [PMID: 32305410] - Daiva Majiene, Jolita Kuseliauskyte, Arturas Stimbirys, Aiste Jekabsone. Comparison of the Effect of Native 1,4-Naphthoquinones Plumbagin, Menadione, and Lawsone on Viability, Redox Status, and Mitochondrial Functions of C6 Glioblastoma Cells.
Nutrients.
2019 Jun; 11(6):. doi:
10.3390/nu11061294. [PMID: 31181639] - Satoshi Endo, Namiki Miyagi, Toshiyuki Matsunaga, Akira Ikari. Rabbit dehydrogenase/reductase SDR family member 11 (DHRS11): Its identity with acetohexamide reductase with broad substrate specificity and inhibitor sensitivity, different from human DHRS11.
Chemico-biological interactions.
2019 May; 305(?):12-20. doi:
10.1016/j.cbi.2019.03.026. [PMID: 30926317] - 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:
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ChemMedChem.
2019 03; 14(5):532-544. doi:
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Journal of agricultural and food chemistry.
2018 Nov; 66(45):11968-11973. doi:
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Anti-cancer drugs.
2018 07; 29(6):520-529. doi:
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2018 02; 20(1):74-84. doi:
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Chemistry & biodiversity.
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Plant & cell physiology.
2012 Jan; 53(1):237-43. doi:
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Genetics and molecular research : GMR.
2011 Dec; 10(4):3236-45. doi:
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Free radical biology & medicine.
2011 Dec; 51(12):2259-71. doi:
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2011 Jun; 26(3):266-79. doi:
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Phytochemistry.
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Bioinorganic chemistry and applications.
2011; 2011(?):898726. doi:
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Journal of biomedicine & biotechnology.
2011; 2011(?):165852. doi:
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Chemical & pharmaceutical bulletin.
2011; 59(1):117-9. doi:
10.1248/cpb.59.117. [PMID: 21212559] - Jin-e Yi, Bozena Obminska-Mrukowicz, Li-yun Yuan, Hui Yuan. Immunomodulatory effects of betulinic acid from the bark of white birch on mice.
Journal of veterinary science.
2010 Dec; 11(4):305-13. doi:
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BMC molecular biology.
2010 Nov; 11(?):88. doi:
10.1186/1471-2199-11-88. [PMID: 21092138] - Pedro Sanchez-Cruz, Carmelo Garcia, Antonio E Alegria. Role of quinones in the ascorbate reduction rates of S-nitrosoglutathione.
Free radical biology & medicine.
2010 Nov; 49(9):1387-94. doi:
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Osteoporosis international : a journal established as result of cooperation between the European Foundation for Osteoporosis and the National Osteoporosis Foundation of the USA.
2010 Aug; 21(8):1437-47. doi:
10.1007/s00198-009-1075-y. [PMID: 19813044] - B Piro, Q D Zhang, S Reisberg, V Noel, L A Dang, H T Duc, M C Pham. Direct and rapid electrochemical immunosensing system based on a conducting polymer.
Talanta.
2010 Jul; 82(2):608-12. doi:
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International journal of Ayurveda research.
2010 Jul; 1(3):163-6. doi:
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Planta medica.
2010 Jun; 76(9):858-62. doi:
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Toxicology in vitro : an international journal published in association with BIBRA.
2010 Apr; 24(3):905-9. doi:
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Journal of Asian natural products research.
2010 Apr; 12(4):286-92. doi:
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Journal of experimental botany.
2010 Mar; 61(3):911-22. doi:
10.1093/jxb/erp359. [PMID: 20018905] - N V Vinod, R Shijina, K V Dileep, C Sadasivan. Inhibition of beta-lactamase by 1,4-naphthalenedione from the plant Holoptelea integrifolia.
Applied biochemistry and biotechnology.
2010 Mar; 160(6):1752-9. doi:
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Planta medica.
2010 Mar; 76(4):345-9. doi:
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Chemico-biological interactions.
2010 Feb; 183(3):369-79. doi:
10.1016/j.cbi.2009.11.030. [PMID: 19962971] - An S Tan, Michael V Berridge. Evidence for NAD(P)H:quinone oxidoreductase 1 (NQO1)-mediated quinone-dependent redox cycling via plasma membrane electron transport: A sensitive cellular assay for NQO1.
Free radical biology & medicine.
2010 Feb; 48(3):421-9. doi:
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Indian journal of biochemistry & biophysics.
2010 Feb; 47(1):53-5. doi:
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Journal of natural medicines.
2010 Jan; 64(1):114-6. doi:
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Pharmacognosy research.
2010 Jan; 2(1):26-30. doi:
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Frontiers in pharmacology.
2010; 1(?):123. doi:
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Sensors (Basel, Switzerland).
2010; 10(7):6290-6306. doi:
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Pharmacognosy reviews.
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Molecules (Basel, Switzerland).
2009 Dec; 14(12):5281-8. doi:
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Electrophoresis.
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Phytomedicine : international journal of phytotherapy and phytopharmacology.
2009 Oct; 16(10):929-34. doi:
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Chemico-biological interactions.
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Mutagenesis.
2009 Sep; 24(5):413-8. doi:
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Journal of chemical ecology.
2009 Aug; 35(8):980-96. doi:
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Biological & pharmaceutical bulletin.
2009 Jul; 32(7):1251-60. doi:
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The Biochemical journal.
2009 Jun; 421(2):231-41. doi:
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Phytomedicine : international journal of phytotherapy and phytopharmacology.
2009 Jun; 16(6-7):581-5. doi:
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International journal of cancer.
2009 May; 124(10):2450-9. doi:
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Chemistry and physics of lipids.
2009 May; 159(1):45-50. doi:
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European journal of pharmacology.
2009 Apr; 607(1-3):234-43. doi:
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Genetics and molecular biology.
2009 Apr; 32(2):382-8. doi:
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Dermatitis : contact, atopic, occupational, drug.
2009 Mar; 20(2):63-78. doi:
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Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.
2008 Nov; 128(11):1681-8. doi:
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Diabetes care.
2008 Nov; 31(11):2092-6. doi:
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Veterinary parasitology.
2008 Oct; 157(1-2):1-8. doi:
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Bioorganic & medicinal chemistry letters.
2008 Oct; 18(20):5387-90. doi:
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Journal of pharmaceutical and biomedical analysis.
2008 Aug; 47(4-5):990-3. doi:
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Biological & pharmaceutical bulletin.
2008 Jul; 31(7):1429-33. doi:
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Journal of separation science.
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