4-Hydroxycoumarin (BioDeep_00000000445)

 

Secondary id: BioDeep_00000279086

human metabolite PANOMIX_OTCML-2023 Volatile Flavor Compounds natural product


代谢物信息卡片


4-Hydroxy Coumarin;4-Coumarinol;4-Hydroxy-2H-chromen-2-one

化学式: C9H6O3 (162.03169259999999)
中文名称: 4-羟基香豆素, 4-羟基香豆精
谱图信息: 最多检出来源 Viridiplantae(plant) 0.35%

分子结构信息

SMILES: C1=CC=C2C(=C1)C(=CC(=O)O2)O
InChI: InChI=1S/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10H

描述信息

4-hydroxycoumarin is a hydroxycoumarin that is coumarin in which the hydrogen at position 4 is replaced by a hydroxy group. It is a conjugate acid of a 4-hydroxycoumarin(1-).
4-Hydroxycoumarin is a natural product found in Vitis vinifera, Ruta graveolens, and Apis cerana with data available.
CONFIDENCE Reference Standard (Level 1); NaToxAq - Natural Toxins and Drinking Water Quality - From Source to Tap (https://natoxaq.ku.dk)
D006401 - Hematologic Agents > D000925 - Anticoagulants > D015110 - 4-Hydroxycoumarins
CONFIDENCE standard compound; INTERNAL_ID 2312
4-Hydroxycoumarin, a coumarin derivative, is one of the most versatile heterocyclic scaffolds and is frequently applied in the synthesis of various organic compounds. 4-Hydroxycoumarin possesses both electrophilic and nucleophilic properties. 4-Hydroxycoumarin derivatives are employed as the anticoagulant, antibacterial, antifungal, antiviral, antitumor, antiprotozoal, insecticidal, antimycobacterial, antimutagenic, antioxidant, anti-inflammatory agents, HIV protease inhibitors and tyrosine kinase inhibitors[1].
4-Hydroxycoumarin, a coumarin derivative, is one of the most versatile heterocyclic scaffolds and is frequently applied in the synthesis of various organic compounds. 4-Hydroxycoumarin possesses both electrophilic and nucleophilic properties. 4-Hydroxycoumarin derivatives are employed as the anticoagulant, antibacterial, antifungal, antiviral, antitumor, antiprotozoal, insecticidal, antimycobacterial, antimutagenic, antioxidant, anti-inflammatory agents, HIV protease inhibitors and tyrosine kinase inhibitors[1].

同义名列表

44 个代谢物同义名

4-Hydroxy Coumarin;4-Coumarinol;4-Hydroxy-2H-chromen-2-one; InChI=1/C9H6O3/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5,10; 4-Hydroxy-2H-1-benzopyran-2-one (4-Hydroxycoumarin); 4-Hydroxycoumarin, Vetec(TM) reagent grade, 98\\%; 4-HYDROXY-1-BENZOPYRAN-2-ONE; 4-HYDROXYCOUMARIN; 5-18-01-00378 (Beilstein Handbook Reference); WARFARIN SODIUM IMPURITY B [EP IMPURITY]; 4H-1-Benzopyran-4-one, 2-hydroxy-; 2H-1-BENZOPYRAN-2-ONE, 4-HYDROXY-; 4-HYDROXYCOUMARIN [USP IMPURITY]; 4-hydroxy-2H-benzo[b]pyran-2-one; 4-Hydroxy-2H-1-benzopyran-2-one; 2-Hydroxy-4H-1-benzopyran-4-one; 4-hydroxy-2-oxo-2H-1-benzopyran; 4-HYDROXY-1-BENZOPYRAN-2-ONE; 4-Hydroxy-2H-chromen-2-one #; 4-Hydroxy-2H-chromen-2-one; 4-Hydroxy-chromen-2-one; 4-Hydroxycoumarin, 98\\%; 4-hydroxychromen-2-one; 4-hydroxy-2-chromenone; 4-Monohydroxycoumarin; Coumarin, 4-hydroxy-; 4-hydroxyl coumarin; 4- Hydroxycoumarin; 4-hydroxy-coumarin; Benzotetronic acid; 4-Hydroxy coumarin; 4-Hydroxycoumarin; 2-Hydroxychromone; 4-hyroxycoumarin; WLN: T66 BOVJ EQ; 4hydroxycoumarin; hydroxychromone; 4-OH coumarin; MEGxm0_000452; ACon1_001952; 4-Coumarinol; ICCB4_000134; NCI60_000453; AI3-52393; Coumarin; 4HC; 4-Hydroxycoumarin



数据库引用编号

61 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

代谢反应

3 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(2)

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。



文献列表

  • Nadia Taïbi, Qosay Ali Al-Balas, Nadjia Bekari, Oualid Talhi, Ghazi Ahmad Al Jabal, Yasmine Benali, Rachid Ameraoui, Mohamed Hadjadj, Amina Taïbi, Zahra Mouna Boutaiba, Mohamed Abou-Mustapha, Farida Khammar, Fayçal Dergal, Ridha Hassaine, Leila Boukenna, Khaldoun Bachari, Artur Manuel Soares Silva. Molecular docking and dynamic studies of a potential therapeutic target inhibiting glyoxalase system: Metabolic action of the 3, 3 '- [3- (5-chloro-2-hydroxyphenyl) -3-oxopropane-1, 1-diyl] - Bis-4-hydroxycoumarin leads overexpression of the intracellular level of methylglyoxal and induction of a pro-apoptotic phenomenon in a hepatocellular carcinoma model. Chemico-biological interactions. 2021 Aug; 345(?):109511. doi: 10.1016/j.cbi.2021.109511. [PMID: 33989593]
  • Joanna Sumorek-Wiadro, Adrian Zając, Ewa Langner, Krystyna Skalicka-Woźniak, Aleksandra Maciejczyk, Wojciech Rzeski, Joanna Jakubowicz-Gil. Antiglioma Potential of Coumarins Combined with Sorafenib. Molecules (Basel, Switzerland). 2020 Nov; 25(21):. doi: 10.3390/molecules25215192. [PMID: 33171577]
  • Hajar Golshadi Ghalehshahi, Saeed Balalaie, Atousa Aliahmadi, Roya Moghimi. Synthesis of 4-N-α-coumaryl amino acids and investigation of their antioxidant, antimicrobial activities and fluorescence spectra. Amino acids. 2018 Oct; 50(10):1461-1470. doi: 10.1007/s00726-018-2624-5. [PMID: 30046883]
  • Yang Gao, Guo-Ning Zhang, Juxian Wang, Xiaoguang Bai, Yiliang Li, Yucheng Wang. One-Pot Syntesis of 3-Functionalized 4-Hydroxycoumarin under Catalyst-Free Conditions. Molecules (Basel, Switzerland). 2018 Jan; 23(1):. doi: 10.3390/molecules23010235. [PMID: 29361771]
  • Zheng Hou, Ying Zhou, Jing Li, Xinlei Zhang, Xin Shi, Xiaoyan Xue, Zhi Li, Bo Ma, Yukun Wang, Mingkai Li, Xiaoxing Luo. Selective in vivo and in vitro activities of 3,3'-4-nitrobenzylidene-bis-4-hydroxycoumarin against methicillin-resistant Staphylococcus aureus by inhibition of DNA polymerase III. Scientific reports. 2015 Sep; 5(?):13637. doi: 10.1038/srep13637. [PMID: 26323712]
  • Milan Mladenović, Mirjana Mihailović, Desanka Bogojević, Nenad Vuković, Slobodan Sukdolak, Sanja Matić, Neda Nićiforović, Vladimir Mihailović, Pavle Mašković, Miroslav M Vrvić, Slavica Solujić. Biochemical and pharmacological evaluation of 4-hydroxychromen-2-ones bearing polar C-3 substituents as anticoagulants. European journal of medicinal chemistry. 2012 Aug; 54(?):144-58. doi: 10.1016/j.ejmech.2012.04.036. [PMID: 22633008]
  • Chung-Yi Chen, Kuo-Chen Cheng, Andy Y Chang, Ying-Ting Lin, You-Cheng Hseu, Hui-Min Wang. 10-Shogaol, an antioxidant from Zingiber officinale for skin cell proliferation and migration enhancer. International journal of molecular sciences. 2012; 13(2):1762-1777. doi: 10.3390/ijms13021762. [PMID: 22408422]
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  • Jae-chul Jung, Hyung-in Moon. Larvicidal activity of 4-hydroxycoumarin derivatives against Aedes aegypti. Pharmaceutical biology. 2011 Feb; 49(2):190-3. doi: 10.3109/13880209.2010.507769. [PMID: 21043993]
  • Sílvia Helena Cestari, Jairo Kennup Bastos, Luiz Claudio Di Stasi. Intestinal Anti-Inflammatory Activity of Baccharis dracunculifolia in the Trinitrobenzenesulphonic Acid Model of Rat Colitis. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):524349. doi: 10.1093/ecam/nep081. [PMID: 19592480]
  • Milan Mladenović, Mirjana Mihailović, Desanka Bogojević, Sanja Matić, Neda Nićiforović, Vladimir Mihailović, Nenad Vuković, Slobodan Sukdolak, Slavica Solujić. In vitro antioxidant activity of selected 4-hydroxy-chromene-2-one derivatives-SAR, QSAR and DFT studies. International journal of molecular sciences. 2011; 12(5):2822-41. doi: 10.3390/ijms12052822. [PMID: 21686153]
  • Amin Al-Shami, Kanchan G Jhaver, Peter Vogel, Carrie Wilkins, Juliane Humphries, John J Davis, Nianhua Xu, David G Potter, Brenda Gerhardt, Robert Mullinax, Cynthia R Shirley, Stephen J Anderson, Tamas Oravecz. Regulators of the proteasome pathway, Uch37 and Rpn13, play distinct roles in mouse development. PloS one. 2010 Oct; 5(10):e13654. doi: 10.1371/journal.pone.0013654. [PMID: 21048919]
  • Vessela D Kancheva, Petya V Boranova, Jordan T Nechev, Ilia I Manolov. Structure-activity relationships of new 4-hydroxy bis-coumarins as radical scavengers and chain-breaking antioxidants. Biochimie. 2010 Sep; 92(9):1138-46. doi: 10.1016/j.biochi.2010.02.033. [PMID: 20211681]
  • Nohemí Salinas-Jazmín, Marisol de la Fuente, Ruth Jaimez, Mayra Pérez-Tapia, Armando Pérez-Torres, Marco A Velasco-Velázquez. Antimetastatic, antineoplastic, and toxic effects of 4-hydroxycoumarin in a preclinical mouse melanoma model. Cancer chemotherapy and pharmacology. 2010 Apr; 65(5):931-40. doi: 10.1007/s00280-009-1100-z. [PMID: 19690859]
  • K S Joseph, Annette C Moser, Sara B G Basiaga, John E Schiel, David S Hage. Evaluation of alternatives to warfarin as probes for Sudlow site I of human serum albumin: characterization by high-performance affinity chromatography. Journal of chromatography. A. 2009 Apr; 1216(16):3492-500. doi: 10.1016/j.chroma.2008.09.080. [PMID: 18926542]
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  • Shujiang Tu, Shanshan Wu, Shu Yan, Wenjuan Hao, Xiaohong Zhang, Xudong Cao, Zhengguo Han, Bo Jiang, Feng Shi, Min Xia, Jianfeng Zhou. Design and microwave-assisted synthesis of naphtho[2,3-f]quinoline derivatives and their luminescent properties. Journal of combinatorial chemistry. 2009 Mar; 11(2):239-42. doi: 10.1021/cc800094m. [PMID: 19115830]
  • Krzysztof Wójtowicz. Comparison of the effect of 4-hydroxycoumarin and umbelliferone on the phase transition of dipalmitoylphosphatidylcholine (DPPC) bilayers. Pharmacological reports : PR. 2008 Jul; 60(4):555-60. doi: . [PMID: 18799825]
  • Carlos L Céspedes, J Guillermo Avila, Andrés Martínez, Blanca Serrato, José C Calderón-Mugica, Rafael Salgado-Garciglia. Antifungal and antibacterial activities of Mexican tarragon (Tagetes lucida). Journal of agricultural and food chemistry. 2006 May; 54(10):3521-7. doi: 10.1021/jf053071w. [PMID: 19127719]
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  • Jian-Tao He, Zhi-Hong Shi, Jin Yan, Mei-Ping Zhao, Zhen-Quan Guo, Wen-Bao Chang. Biotin-avidin amplified enzyme-linked immunosorbent assay for determination of isoflavone daidzein. Talanta. 2005 Feb; 65(3):621-6. doi: 10.1016/j.talanta.2004.07.027. [PMID: 18969844]
  • Hideki Kanho, Sayaka Yaoya, Tomio Itani, Takahisa Nakane, Nobuo Kawahara, Yoichi Takase, Kazuo Masuda, Masanori Kuroyanagi. Glucosylation of phenolic compounds by Pharbitis nil hairy roots: I. Glucosylation of coumarin and flavone derivatives. Bioscience, biotechnology, and biochemistry. 2004 Oct; 68(10):2032-9. doi: 10.1271/bbb.68.2032. [PMID: 15502347]
  • Anna Oliva, Kumudini M Meepagala, David E Wedge, Dewayne Harries, Amber L Hale, Giovanni Aliotta, Stephen O Duke. Natural fungicides from Ruta graveolens L. leaves, including a new quinolone alkaloid. Journal of agricultural and food chemistry. 2003 Feb; 51(4):890-6. doi: 10.1021/jf0259361. [PMID: 12568545]
  • Claudia Bocca, Ludovica Gabriel, Francesca Bozzo, Antonella Miglietta. Microtubule-interacting activity and cytotoxicity of the prenylated coumarin ferulenol. Planta medica. 2002 Dec; 68(12):1135-7. doi: 10.1055/s-2002-36342. [PMID: 12494346]
  • L Vander Elst, S Laurent, H M Bintoma, R N Muller. Albumin-bound MRI contrast agents: the dilemma of the rotational correlation time. Magma (New York, N.Y.). 2001 May; 12(2-3):135-40. doi: 10.1007/bf02668095. [PMID: 11390269]
  • Y Masamoto. [Sensitization and crossreaction of simple coumarins]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 2001 Jan; 121(1):97-103. doi: 10.1248/yakushi.121.97. [PMID: 11201168]
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  • D Lamnaouer. [Anticoagulant activity of coumarins from Ferula communis L]. Therapie. 1999 Nov; 54(6):747-51. doi: ". [PMID: 10709451]
  • H H Maurer, J W Arlt. Detection of 4-hydroxycoumarin anticoagulants and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation. Journal of chromatography. B, Biomedical sciences and applications. 1998 Sep; 714(2):181-95. doi: 10.1016/s0378-4347(98)00243-6. [PMID: 9766858]
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  • S ROSEMAN, H GREEN. A colorimetric method for the determination of dicumarol (3,3'-methylenebis (4-hydroxycoumarin)) in plasma. The Journal of laboratory and clinical medicine. 1951 Feb; 37(2):321-4. doi: NULL. [PMID: 14814360]
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  • J AXELROD, J R COOPER, B B BRODIE. Estimation of dicumarol, 3,31-methylenebis (4-hydroxycoumarin) in biological fluids. Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.). 1949 Apr; 70(4):693-5. doi: 10.3181/00379727-70-17036. [PMID: 18144836]
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