5-5'-Dehydrodiferulic acid (BioDeep_00000004358)
human metabolite PANOMIX_OTCML-2023
代谢物信息卡片
化学式: C20H18O8 (386.1002)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(not specific) 50%
分子结构信息
SMILES: c1c(cc(c(c1OC)O)c1cc(cc(c1O)OC)/C=C/C(=O)O)/C=C/C(=O)O
InChI: InChI=1S/C20H18O8/c1-27-15-9-11(3-5-17(21)22)7-13(19(15)25)14-8-12(4-6-18(23)24)10-16(28-2)20(14)26/h3-10,25-26H,1-2H3,(H,21,22)(H,23,24)/b5-3+,6-4+
描述信息
5-5-dehydrodiferulic acid, also known as 8-O-4-diferulic acid, belongs to biphenyls and derivatives class of compounds. Those are organic compounds containing to benzene rings linked together by a C-C bond. 5-5-dehydrodiferulic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 5-5-dehydrodiferulic acid can be found in a number of food items such as corn, common wheat, semolina, and hard wheat, which makes 5-5-dehydrodiferulic acid a potential biomarker for the consumption of these food products.
同义名列表
10 个代谢物同义名
(2E)-3-(3-{5-[(1E)-2-carboxyeth-1-en-1-yl]-2-hydroxy-3-methoxyphenyl}-4-hydroxy-5-methoxyphenyl)prop-2-enoic acid; (2E)-3-{5-[(1E)-2-carboxyeth-1-en-1-yl]-2,6-dihydroxy-3,5-dimethoxy-[1,1-biphenyl]-3-yl}prop-2-enoate; 5-5-Dehydrodiferulic acid; 5-5-Dehydrodiferulate; 8-5-b Diferulic acid; 8-O-4-Diferulic acid; 8-5-Diferulic acid; Diferulic acid; DTXSID90331951; Diferulic acid
数据库引用编号
16 个数据库交叉引用编号
- KEGG: C10446
- PubChem: 5281770
- PubChem: 442785
- HMDB: HMDB0301718
- Metlin: METLIN68330
- KNApSAcK: C00002734
- foodb: FDB000263
- chemspider: 4445083
- CAS: 60299-54-9
- CAS: 436-96-4
- PMhub: MS000016729
- PubChem: 12629
- 3DMET: B03852
- NIKKAJI: J82.063F
- LOTUS: LTS0164735
- wikidata: Q105149578
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)
6 个相关的物种来源信息
- 41057 - Aspergillus unilateralis: 10.1002/CHIN.200523199
- 4498 - Avena sativa: 10.1034/J.1399-3054.1994.920222.X
- 9606 - Homo sapiens: -
- 4550 - Secale cereale:
- 4565 - Triticum aestivum: 10.1016/J.FOODCHEM.2005.07.053
- 4577 - Zea mays: 10.1021/JF020957G
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
- Neng-Wen Yin, Shu-Xian Wang, Le-Dong Jia, Mei-Chen Zhu, Jing Yang, Bao-Jin Zhou, Jia-Ming Yin, Kun Lu, Rui Wang, Jia-Na Li, Cun-Min Qu. Identification and Characterization of Major Constituents in Different-Colored Rapeseed Petals by UPLC-HESI-MS/MS.
Journal of agricultural and food chemistry.
2019 Oct; 67(40):11053-11065. doi:
10.1021/acs.jafc.9b05046. [PMID: 31525973] - Yuan Jia, Ying He, Fachuang Lu. The structure-antioxidant activity relationship of dehydrodiferulates.
Food chemistry.
2018 Dec; 269(?):480-485. doi:
10.1016/j.foodchem.2018.07.038. [PMID: 30100463] - Hongcheng Zhang, Yafang Shao, Jinsong Bao, Trust Beta. Phenolic compounds and antioxidant properties of breeding lines between the white and black rice.
Food chemistry.
2015 Apr; 172(?):630-9. doi:
10.1016/j.foodchem.2014.09.118. [PMID: 25442600] - Jiří Grúz, Jiří Pospíšil, Hana Kozubíková, Tomáš Pospíšil, Karel Doležal, Mirko Bunzel, Miroslav Strnad. Determination of free diferulic, disinapic and dicoumaric acids in plants and foods.
Food chemistry.
2015 Mar; 171(?):280-6. doi:
10.1016/j.foodchem.2014.08.131. [PMID: 25308670] - Kazuyuki Wakabayashi, Kouichi Soga, Takayuki Hoson, Toshihisa Kotake, Takashi Yamazaki, Akira Higashibata, Noriaki Ishioka, Toru Shimazu, Keiji Fukui, Ikuko Osada, Haruo Kasahara, Motoshi Kamada. Suppression of Hydroxycinnamate Network Formation in Cell Walls of Rice Shoots Grown under Microgravity Conditions in Space.
PloS one.
2015; 10(9):e0137992. doi:
10.1371/journal.pone.0137992. [PMID: 26378793] - Luca Calani, Fayçal Ounnas, Patricia Salen, Christine Demeilliers, Letizia Bresciani, Francesca Scazzina, Furio Brighenti, Camilla Melegari, Alan Crozier, Michel de Lorgeril, Daniele Del Rio. Bioavailability and metabolism of hydroxycinnamates in rats fed with durum wheat aleurone fractions.
Food & function.
2014 Aug; 5(8):1738-46. doi:
10.1039/c4fo00328d. [PMID: 24977665] - Md Nesar Uddin, Stefan Hanstein, Franziska Faust, Philipp T Eitenmüller, Britta Pitann, Sven Schubert. Diferulic acids in the cell wall may contribute to the suppression of shoot growth in the first phase of salt stress in maize.
Phytochemistry.
2014 Jun; 102(?):126-36. doi:
10.1016/j.phytochem.2014.02.014. [PMID: 24661612] - Ramin Vismeh, Fachuang Lu, Shishir P S Chundawat, James F Humpula, Ali Azarpira, Venkatesh Balan, Bruce E Dale, John Ralph, A Daniel Jones. Profiling of diferulates (plant cell wall cross-linkers) using ultrahigh-performance liquid chromatography-tandem mass spectrometry.
The Analyst.
2013 Nov; 138(21):6683-92. doi:
10.1039/c3an36709f. [PMID: 24040649] - Terri Grassby, Andrew J Jay, Zara Merali, Mary L Parker, Adrian J Parr, Craig B Faulds, Keith W Waldron. Compositional analysis of Chinese water chestnut (Eleocharis dulcis) cell-wall material from parenchyma, epidermis, and subepidermal tissues.
Journal of agricultural and food chemistry.
2013 Oct; 61(40):9680-8. doi:
10.1021/jf401863n. [PMID: 24066627] - Fachuang Lu, Liping Wei, Ali Azarpira, John Ralph. Rapid syntheses of dehydrodiferulates via biomimetic radical coupling reactions of ethyl ferulate.
Journal of agricultural and food chemistry.
2012 Aug; 60(34):8272-7. doi:
10.1021/jf302140k. [PMID: 22846085] - Kazuyuki Wakabayashi, Kouichi Soga, Takayuki Hoson. Phenylalanine ammonia-lyase and cell wall peroxidase are cooperatively involved in the extensive formation of ferulate network in cell walls of developing rice shoots.
Journal of plant physiology.
2012 Feb; 169(3):262-7. doi:
10.1016/j.jplph.2011.10.002. [PMID: 22118877] - Kazuyuki Wakabayashi, Kouichi Soga, Takayuki Hoson. Cell wall oxalate oxidase modifies the ferulate metabolism in cell walls of wheat shoots.
Journal of plant physiology.
2011 Nov; 168(16):1997-2000. doi:
10.1016/j.jplph.2011.05.010. [PMID: 21684033] - Alexander Ulanov, Anatoliy Lygin, David Duncan, Jack Widholm, Vera Lozovaya. Metabolic effects of glyphosate change the capacity of maize culture to regenerate plants.
Journal of plant physiology.
2009 Jun; 166(9):978-87. doi:
10.1016/j.jplph.2008.11.004. [PMID: 19110340] - Shona E Lindsay, Stephen C Fry. Control of diferulate formation in dicotyledonous and gramineous cell-suspension cultures.
Planta.
2008 Jan; 227(2):439-52. doi:
10.1007/s00425-007-0630-z. [PMID: 17938956] - Mohammad Talim Hossain, Kouichi Soga, Kazuyuki Wakabayashi, Seiichiro Kamisaka, Shuhei Fujii, Ryoichi Yamamoto, Takayuki Hoson. Modification of chemical properties of cell walls by silicon and its role in regulation of the cell wall extensibility in oat leaves.
Journal of plant physiology.
2007 Apr; 164(4):385-93. doi:
10.1016/j.jplph.2006.02.003. [PMID: 16618521] - Carola Funk, Annett Braune, John H Grabber, Hans Steinhart, Mirko Bunzel. Moderate ferulate and diferulate levels do not impede maize cell wall degradation by human intestinal microbiota.
Journal of agricultural and food chemistry.
2007 Mar; 55(6):2418-23. doi:
10.1021/jf063109k. [PMID: 17319685] - Rogelio Santiago, Ana Butrón, Lana M Reid, John T Arnason, German Sandoya, Xose C Souto, Rosa A Malvar. Diferulate content of maize sheaths is associated with resistance to the Mediterranean corn borer Sesamia nonagrioides (Lepidoptera: Noctuidae).
Journal of agricultural and food chemistry.
2006 Nov; 54(24):9140-4. doi:
10.1021/jf061830k. [PMID: 17117802] - E Larsen, M F Andreasen, L P Christensen. Regioselective dimerization of ferulic acid in a micellar solution.
Journal of agricultural and food chemistry.
2001 Jul; 49(7):3471-5. doi:
10.1021/jf0014617. [PMID: 11453793]
