Caffeic acid ethyl ester (BioDeep_00000017270)

human metabolite PANOMIX_OTCML-2023

代谢物信息卡片

2-Propenoic acid, 3-(3,4-dihydroxyphenyl)-, ethyl ester

化学式: C11H12O4 (208.0735552)
中文名称: 3,4-二羟基肉桂酸乙酯, 咖啡酸乙酯, 3,4-二羟基肉桂酸乙酯, 咖啡酸乙酯
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 6.74%

分子结构信息

SMILES: c1c(c(cc(c1)/C=C/C(=O)OCC)O)O
InChI: InChI=1S/C11H12O4/c1-2-15-11(14)6-4-8-3-5-9(12)10(13)7-8/h3-7,12-13H,2H2,1H3/b6-4+

描述信息

Caffeic acid ethyl ester, also known as (E)-ethyl 3,4-dihydroxycinnamate or (E)-ethyl caffeate, belongs to coumaric acids and derivatives class of compounds. Those are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Caffeic acid ethyl ester is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Caffeic acid ethyl ester can be found in eggplant and vinegar, which makes caffeic acid ethyl ester a potential biomarker for the consumption of these food products. Ethyl caffeate is an ester of an hydroxycinnamic acid, a naturally occurring organic compound .
Ethyl trans-caffeate is an ethyl ester resulting from the formal condensation of the carboxy group of trans-caffeic acid with ethanol. It has a role as an anti-inflammatory agent and an antineoplastic agent. It is an alkyl caffeate ester and an ethyl ester. It is functionally related to a trans-caffeic acid.
Ethyl caffeate is a natural product found in Cichorium endivia, Cichorium pumilum, and other organisms with data available.
Ethyl Caffeate is a natural phenolic compound isolated from Bidens pilosa. Ethyl caffeate suppresses NF-κB activation and its downstream inflammatory mediators, inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), and prostaglandin E2 (PGE2) in vitro or in mouse skin[1].
Ethyl Caffeate is a natural phenolic compound isolated from Bidens pilosa. Ethyl caffeate suppresses NF-κB activation and its downstream inflammatory mediators, inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), and prostaglandin E2 (PGE2) in vitro or in mouse skin[1].

同义名列表

42 个代谢物同义名

数据库引用编号

15 个数据库交叉引用编号

ChEBI: CHEBI:132714
ChEBI: CHEBI:69656
PubChem: 5317238
HMDB: HMDB0301712
ChEMBL: CHEMBL17347
Wikipedia: Ethyl_caffeate
MeSH: ethyl caffeate
ChemIDplus: 0000102374
KNApSAcK: C00030221
foodb: FDB000243
chemspider: 4476132
CAS: 66648-50-8
CAS: 102-37-4
medchemexpress: HY-N6966A
medchemexpress: HY-N6966

分类词条

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)

92 个相关的物种来源信息

4111 Solanum melongena:
1227633 Artemisia minor:
29818 Plantago major: 10.1055/S-0028-1099839
2291104 Vincetoxicum shaanxiense:
35883 Ipomoea nil: 10.1248/CPB.59.1425
114281 Cichorium pumilum: 10.1007/S10600-007-0166-2
114280 Cichorium endivia:
1405821 Cichorium glandulosum: 10.1007/S10600-007-0166-2
556514 Lespedeza bicolor: 10.1016/J.FITOTE.2003.07.012
204131 Isodon coetsa: 10.1016/J.PHYMED.2007.09.013
39271 Agastache rugosa: 10.1021/ACS.JNATPROD.9B00697.S001
662928 Isodon sculponeatus: 10.1002/CHIN.200624175
48386 Perilla frutescens: 10.1016/J.FITOTE.2018.08.006
186723 Berberis darwinii: 10.1002/9780470514344.CH14
291319 Incarvillea mairei: 10.1007/S10600-010-9540-6
291320 Incarvillea mairei var. grandiflora: 10.1007/S10600-010-9540-6
662907 Isodon eriocalyx: 10.1021/NP9804278
1570962 Tocoyena formosa: 10.1016/S0031-9422(97)00238-0
4112 Solanum nigrum: 10.5012/BKCS.2010.31.01.199
751879 Ziziphora clinopodioides: 10.1248/CPB.60.397
41468 Adenocaulon himalaicum: 10.1007/BF00579831
2798898 Adenocaulon adhaerescens: 10.1007/BF00579831
75960 Cicerbita muralis: 10.1016/S0031-9422(97)80019-2
254913 Saussurea laniceps: 10.1002/HLCA.200790096
262732 Ligularia nelumbifolia: 10.1016/S0031-9422(00)89547-3
576365 Xanthium sibiricum: 10.1021/NP500951S
2731603 Epicharis densiflora: 10.1016/J.PHYTOCHEM.2008.09.017
262729 Ligularia veitchiana:
49657 Smilax china: 10.1016/J.PHYTOCHEM.2006.10.026
1221114 Leptolobium bijugum: 10.1016/S0305-1978(01)00055-2
39358 Prunella vulgaris: 10.1016/S1001-0742(14)60648-3
291324 Incarvillea delavayi: 10.1007/S10600-010-9598-1
97321 Prunus serrulata: 10.1007/BF00598279
16922 Camptotheca acuminata: 10.1002/JCCS.198500029
632161 Aconitum kongboense: 10.1007/S10600-011-0084-1
588385 Tillandsia recurvata: 10.1016/J.FITOTE.2004.01.003
222879 Harpagophytum procumbens: 10.1016/J.JPBA.2011.02.029
265785 Atractylodes macrocephala: 10.1007/S10600-011-9795-6
1548336 Cyrtocymura scorpioides: 10.1016/J.PHYTOCHEM.2010.06.007
98504 Matricaria chamomilla: 10.1016/J.BSE.2007.03.008
261776 Helichrysum arenarium: 10.1007/S10600-011-9772-0
244311 Erigeron breviscapus: 10.4268/CJCMM20111111
204224 Salvia guaranitica: 10.1016/S0944-7113(96)80006-7
4111 Solanum melongena:
1227633 Artemisia minor:
29818 Plantago major: 10.1055/S-0028-1099839
2291104 Vincetoxicum shaanxiense:
35883 Ipomoea nil: 10.1248/CPB.59.1425
114281 Cichorium pumilum: 10.1007/S10600-007-0166-2
114280 Cichorium endivia:
1405821 Cichorium glandulosum: 10.1007/S10600-007-0166-2
556514 Lespedeza bicolor: 10.1016/J.FITOTE.2003.07.012
204131 Isodon coetsa: 10.1016/J.PHYMED.2007.09.013
39271 Agastache rugosa: 10.1021/ACS.JNATPROD.9B00697.S001
662928 Isodon sculponeatus: 10.1002/CHIN.200624175
48386 Perilla frutescens: 10.1016/J.FITOTE.2018.08.006
186723 Berberis darwinii: 10.1002/9780470514344.CH14
291319 Incarvillea mairei: 10.1007/S10600-010-9540-6
291320 Incarvillea mairei var. grandiflora: 10.1007/S10600-010-9540-6
662907 Isodon eriocalyx: 10.1021/NP9804278
1570962 Tocoyena formosa: 10.1016/S0031-9422(97)00238-0
4112 Solanum nigrum: 10.5012/BKCS.2010.31.01.199
751879 Ziziphora clinopodioides: 10.1248/CPB.60.397
41468 Adenocaulon himalaicum: 10.1007/BF00579831
2798898 Adenocaulon adhaerescens: 10.1007/BF00579831
75960 Cicerbita muralis: 10.1016/S0031-9422(97)80019-2
254913 Saussurea laniceps: 10.1002/HLCA.200790096
262732 Ligularia nelumbifolia: 10.1016/S0031-9422(00)89547-3
576365 Xanthium sibiricum: 10.1021/NP500951S
2731603 Epicharis densiflora: 10.1016/J.PHYTOCHEM.2008.09.017
262729 Ligularia veitchiana:
49657 Smilax china: 10.1016/J.PHYTOCHEM.2006.10.026
1221114 Leptolobium bijugum: 10.1016/S0305-1978(01)00055-2
39358 Prunella vulgaris: 10.1016/S1001-0742(14)60648-3
291324 Incarvillea delavayi: 10.1007/S10600-010-9598-1
97321 Prunus serrulata: 10.1007/BF00598279
16922 Camptotheca acuminata: 10.1002/JCCS.198500029
632161 Aconitum kongboense: 10.1007/S10600-011-0084-1
588385 Tillandsia recurvata: 10.1016/J.FITOTE.2004.01.003
222879 Harpagophytum procumbens: 10.1016/J.JPBA.2011.02.029
265785 Atractylodes macrocephala: 10.1007/S10600-011-9795-6
1548336 Cyrtocymura scorpioides: 10.1016/J.PHYTOCHEM.2010.06.007
98504 Matricaria chamomilla: 10.1016/J.BSE.2007.03.008
261776 Helichrysum arenarium: 10.1007/S10600-011-9772-0
244311 Erigeron breviscapus: 10.4268/CJCMM20111111
204224 Salvia guaranitica: 10.1016/S0944-7113(96)80006-7
9606 Homo sapiens: -
569774 金线莲: -
4111 Solanum Melongena L: -
244311 Erigeron Breviscapus: -
516067 Clerodendranthus spicatus: -
33090 Plants: -

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

Tianming Wang, Min Pan, Nan Xiao, Jiadi Wu, Qirui Wang, Ting Cheng, Guiming Yan, Daqiang Wu, Ning Li, Jing Shao. In vitro and in vivo analysis of monotherapy and dual therapy with ethyl caffeate and fluconazole on virulence factors of Candida albicans and systemic candidiasis. Journal of global antimicrobial resistance. 2021 12; 27(?):253-266. doi: 10.1016/j.jgar.2021.10.005. [PMID: 34700054]
Young Hye Seo, Tuy An Trinh, Seung Mok Ryu, Hyo Seon Kim, Goya Choi, Byeong Cheol Moon, Sang Hee Shim, Dae Sik Jang, Dongho Lee, Ki Sung Kang, Jun Lee. Chemical Constituents from the Aerial Parts of Elsholtzia ciliata and Their Protective Activities on Glutamate-Induced HT22 Cell Death. Journal of natural products. 2020 10; 83(10):3149-3155. doi: 10.1021/acs.jnatprod.0c00756. [PMID: 32991171]
Young H Seo, Shin-Young Kang, Ji-Sun Shin, Seung M Ryu, A Y Lee, Goya Choi, Byeong C Moon, Dae-Sik Jang, Sang H Shim, Dongho Lee, Kyung-Tae Lee, Jun Lee. Chemical Constituents from the Aerial Parts of Agastache rugosa and Their Inhibitory Activities on Prostaglandin E2 Production in Lipopolysaccharide-Treated RAW 264.7 Macrophages. Journal of natural products. 2019 12; 82(12):3379-3385. doi: 10.1021/acs.jnatprod.9b00697. [PMID: 31747281]
Shangde Sun, Ping Wang, Sha Zhu. Enzymatic incorporation of caffeoyl into castor oil to prepare the novel castor oil-based caffeoyl structured lipids. Journal of biotechnology. 2017 May; 249(?):66-72. doi: 10.1016/j.jbiotec.2017.03.022. [PMID: 28344155]
Shikui Xu, Aixue Zuo, Zengjun Guo, Chunping Wan. Ethyl Caffeate Ameliorates Collagen-Induced Arthritis by Suppressing Th1 Immune Response. Journal of immunology research. 2017; 2017(?):7416792. doi: 10.1155/2017/7416792. [PMID: 28706956]
Shangde Sun, Bingxue Hu. A novel method for the synthesis of glyceryl monocaffeate by the enzymatic transesterification and kinetic analysis. Food chemistry. 2017 Jan; 214(?):192-198. doi: 10.1016/j.foodchem.2016.07.087. [PMID: 27507465]
Lu Zhang, Zong-Cai Tu, Tao Yuan, Hui Wang, Xing Xie, Zhi-Feng Fu. Antioxidants and α-glucosidase inhibitors from Ipomoea batatas leaves identified by bioassay-guided approach and structure-activity relationships. Food chemistry. 2016 Oct; 208(?):61-7. doi: 10.1016/j.foodchem.2016.03.079. [PMID: 27132824]
Xiao-mei Fu, de-hong Liu, Yan-chao Sun, Jing Liu, Jian-guo Pei, Zhi-gui Wu. [Chemical Constituents from Xanthium mongolicum]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2016 Jun; 39(6):1308-10. doi: ". [PMID: 30156804]
Ganggang Luo, Fang Lu, Liansheng Qiao, Xi Chen, Gongyu Li, Yanling Zhang. Discovery of Potential Inhibitors of Aldosterone Synthase from Chinese Herbs Using Pharmacophore Modeling, Molecular Docking, and Molecular Dynamics Simulation Studies. BioMed research international. 2016; 2016(?):4182595. doi: 10.1155/2016/4182595. [PMID: 27781210]
Xiao Zhang, Jiang-rui Wang, Qin-mei Zhou, Li Guo, Liang Xiong, Su-ying Gou. [Study on Chemical Constituents of Lonicera similis]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2015 Nov; 38(11):2324-6. doi: ". [PMID: 27356385]
Yu-Sheng Shi, Yun-Bao Liu, Shuang-Gang Ma, Yong Li, Jing Qu, Li Li, Shao-Peng Yuan, Qi Hou, Yu-Huan Li, Jian-Dong Jiang, Shi-Shan Yu. Bioactive Sesquiterpenes and Lignans from the Fruits of Xanthium sibiricum. Journal of natural products. 2015 Jul; 78(7):1526-35. doi: 10.1021/np500951s. [PMID: 26110443]
Takeshi Yokoyama, Yuto Kosaka, Mineyuki Mizuguchi. Inhibitory activities of propolis and its promising component, caffeic acid phenethyl ester, against amyloidogenesis of human transthyretin. Journal of medicinal chemistry. 2014 Nov; 57(21):8928-35. doi: 10.1021/jm500997m. [PMID: 25314129]
Yao Lu, Zhi-Hong Li, Lin Ma, An-Jun Deng, Feng Wu, Zhi-Hui Zhang, Hai-Lin Qin. [Study on chemical constituents from cultivated Gynura nepalensis]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2014 Oct; 39(19):3777-81. doi: . [PMID: 25612439]
Do Young Lim, Mee-Hyun Lee, Seung Ho Shin, Hanyoung Chen, Joohyun Ryu, Lei Shan, Honglin Li, Ann M Bode, Wei-Dong Zhang, Zigang Dong. (+)-2-(1-Hydroxyl-4-oxocyclohexyl) ethyl caffeate suppresses solar UV-induced skin carcinogenesis by targeting PI3K, ERK1/2, and p38. Cancer prevention research (Philadelphia, Pa.). 2014 Aug; 7(8):856-65. doi: 10.1158/1940-6207.capr-13-0286. [PMID: 24845061]
Yong Zhao, Chang-An Geng, Chang-Li Sun, Yun-Bao Ma, Xiao-Yan Huang, Tuan-Wu Cao, Kang He, Hao Wang, Xue-Mei Zhang, Ji-Jun Chen. Polyacetylenes and anti-hepatitis B virus active constituents from Artemisia capillaris. Fitoterapia. 2014 Jun; 95(?):187-93. doi: 10.1016/j.fitote.2014.03.017. [PMID: 24685503]
Yi-Wen Mao, Hsiang-Wen Tseng, Wen-Li Liang, Ih-Sheng Chen, Shui-Tein Chen, Mei-Hsien Lee. Anti-inflammatory and free radial scavenging activities of the constituents isolated from Machilus zuihoensis. Molecules (Basel, Switzerland). 2011 Nov; 16(11):9451-66. doi: 10.3390/molecules16119451. [PMID: 22075574]
Li Li, Renbing Shi, Tana Wu-Lan, Liji Xu, Yong Peng, Peigen Xiao. [Chemical contituents in leaves of Ehretia thyrsiflora]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2010 Feb; 35(3):331-2. doi: 10.4268/cjcmm20100316. [PMID: 20422999]
Zhi-Zhou He, Ju-Fang Yan, Zhi-Jun Song, Fei Ye, Xun Liao, Shu-Lin Peng, Li-Sheng Ding. Chemical constituents from the aerial parts of Artemisia minor. Journal of natural products. 2009 Jun; 72(6):1198-201. doi: 10.1021/np800643n. [PMID: 19476336]
Q-L Li, B-G Li, Y Zhang, X-P Gao, C-Q Li, G-L Zhang. Three angiotensin-converting enzyme inhibitors from Rabdosia coetsa. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2008 May; 15(5):386-8. doi: 10.1016/j.phymed.2007.09.013. [PMID: 17977703]
Dong-bao Zhao, Wei Zhang, Ming-jing Li, Xiu-hua Liu. [Studies on chemical constituents of Acroptilon repens]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 Nov; 31(22):1869-72. doi: . [PMID: 17285986]
Zhong Dai, Feng Wang, Gang-Li Wang, Rui-Chao Lin. [Studies on chemical constituents of Balanophora spicata]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 Nov; 31(21):1798-800. doi: ". [PMID: 17260797]
Hao-bin Hu, Gen-wang Wang, Jian-xin Liu, Hong Cao, Xu-dong Zheng. [Studies on phenolic compounds from Polygonum aviculane]. Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica. 2006 May; 31(9):740-2. doi: ". [PMID: 17048681]
Yi-Ming Chiang, Chiu-Ping Lo, Yi-Ping Chen, Sheng-Yang Wang, Ning-Sun Yang, Yueh-Hsiung Kuo, Lie-Fen Shyur. Ethyl caffeate suppresses NF-kappaB activation and its downstream inflammatory mediators, iNOS, COX-2, and PGE2 in vitro or in mouse skin. British journal of pharmacology. 2005 Oct; 146(3):352-63. doi: 10.1038/sj.bjp.0706343. [PMID: 16041399]
Yanjun Yang, Jiehong Lin. [Studies on the constituents from Sambucus chinese]. Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials. 2004 Jul; 27(7):491-2. doi: ". [PMID: 15551963]
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