N6-cis-p-Coumaroylserotonin (BioDeep_00000017447)

   

human metabolite PANOMIX_OTCML-2023


代谢物信息卡片


2-Propenamide, N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)-3-(4-hydroxyphenyl)-, (2E)-

化学式: C19H18N2O3 (322.1317358)
中文名称: N-(P-香豆酰)-羟色胺
谱图信息: 最多检出来源 Viridiplantae(plant) 0.07%

分子结构信息

SMILES: C1=CC(=CC=C1C=CC(=O)NCCC2=CNC3=C2C=C(C=C3)O)O
InChI: InChI=1S/C19H18N2O3/c22-15-4-1-13(2-5-15)3-8-19(24)20-10-9-14-12-21-18-7-6-16(23)11-17(14)18/h1-8,11-12,21-23H,9-10H2,(H,20,24)/b8-3+

描述信息

N6-cis-p-Coumaroylserotonin is a member of hydroxyindoles and a carboxamide. It is functionally related to a serotonin.
N-Coumaroyl serotonin is a natural product found in Echinochloa esculenta, Centaurea montana, and other organisms with data available.
Ipobscurine A is found in fats and oils. Ipobscurine A is an alkaloid from Carthamus tinctorius (safflower).
N-(p-Coumaroyl) Serotonin is a polyphenol isolated from the seeds of safflower and has antioxidative, anti-atherogenic and anti-inflammatory properties. N-(p-Coumaroyl) Serotonin inhibits PDGF-induced on phosphorylation of PDGF receptor and Ca2+ release from sarcoplasmic reticulum[1]. N-(p-Coumaroyl) Serotonin ameliorates atherosclerosis and distensibility of the aortic wall in vivo and is usually used for the atherosclerosis research[2].
N-(p-Coumaroyl) Serotonin is a polyphenol isolated from the seeds of safflower and has antioxidative, anti-atherogenic and anti-inflammatory properties. N-(p-Coumaroyl) Serotonin inhibits PDGF-induced on phosphorylation of PDGF receptor and Ca2+ release from sarcoplasmic reticulum[1]. N-(p-Coumaroyl) Serotonin ameliorates atherosclerosis and distensibility of the aortic wall in vivo and is usually used for the atherosclerosis research[2].

同义名列表

29 个代谢物同义名

2-Propenamide, N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)-3-(4-hydroxyphenyl)-, (2E)-; 2-Propenamide, N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)-3-(4-hydroxyphenyl)-, (E)-; (2E)-N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enimidate; (2E)-N-[2-(5-HYDROXY-1H-INDOL-3-YL)ETHYL]-3-(4-HYDROXYPHENYL)PROP-2-ENAMIDE; (E)-N-[2-(5-hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)prop-2-enamide; N-[2-(5-Hydroxy-1H-indol-3-yl)ethyl]-3-(4-hydroxyphenyl)-2-propenamide; (E)-N-(2-(5-hydroxy-1H-indol-3-yl)ethyl)-3-(4-hydroxyphenyl)acrylamide; N-(2-(5-Hydroxy-1H-indol-3-yl)ethyl)-3-(4-hydroxyphenyl)acrylamide; N-[2-(5-hydroxy-1h-indol-3-yl)ethyl]-p-coumaramide; p-coumaric acid serotonin amide; SEROTONIN II, N (P-COUMAROYL)-; 5-Hydroxy-N-feruloyltryptamine; trans-N-(p-Coumaroyl)serotonin; N-COUMAROYL SEROTONIN [INCI]; WLZPAFGVOWCVMG-FPYGCLRLSA-N; N6-cis-p-Coumaroylserotonin; N-(p-Coumaroyl) Serotonin; n-(p-coumaroyl)serotonin; TRYPTAMINE, 5-HYDROXY-N-; N-(p-oumaroyl) serotonin; N-P-Coumaroyl Serotonin; Coumaroylserotonin 98; N-Coumaroyl serotonin; 4-coumaroylserotonin; p-coumaroylserotonin; UNII-IUC27Q8ACH; p-C-serotonin; IUC27Q8ACH; N-p-Coumaroylserotonin



数据库引用编号

15 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

4 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(3)

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。



文献列表

  • Chan Hum Park, Ah Young Lee, Ji Hyun Kim, Su Hui Seong, Eun Ju Cho, Jae Sue Choi, Min Jo Kim, Siyoung Yang, Takako Yokozawa, Yu Su Shin. Protective Effects of Serotonin and its Derivatives, N-Feruloylserotonin and N-(p-Coumaroyl) Serotonin, Against Cisplatin-Induced Renal Damage in Mice. The American journal of Chinese medicine. 2019; 47(2):369-383. doi: 10.1142/s0192415x19500186. [PMID: 30827154]
  • Xiao Tian, Sen Guo, Kan He, Marc Roller, Meiqi Yang, Qingchao Liu, Li Zhang, Chi-Tang Ho, Naisheng Bai. Qualitative and quantitative analysis of chemical constituents of Ptychopetalum olacoides Benth. Natural product research. 2018 Feb; 32(3):354-357. doi: 10.1080/14786419.2017.1354187. [PMID: 28750557]
  • Le-Le Zhang, Ke Tian, Zheng-Hai Tang, Xiao-Jia Chen, Zhao-Xiang Bian, Yi-Tao Wang, Jin-Jian Lu. Phytochemistry and Pharmacology of Carthamus tinctorius L. The American journal of Chinese medicine. 2016; 44(2):197-226. doi: 10.1142/s0192415x16500130. [PMID: 27080938]
  • Mutalib A Aderogba, Ashwell R Ndhlala, Kannan R R Rengasamy, Johannes Van Staden. Antimicrobial and selected in vitro enzyme inhibitory effects of leaf extracts, flavonols and indole alkaloids isolated from Croton menyharthii. Molecules (Basel, Switzerland). 2013 Oct; 18(10):12633-44. doi: 10.3390/molecules181012633. [PMID: 24126380]
  • Toshiyuki Takahashi, Mitsuo Miyazawa. Potent α-glucosidase inhibitors from safflower (Carthamus tinctorius L.) seed. Phytotherapy research : PTR. 2012 May; 26(5):722-6. doi: 10.1002/ptr.3622. [PMID: 22021176]
  • Sung-Hee Cho, Eun-Jung Park, Eun-Ok Kim, Sang-Won Choi. Study on the hypochlolesterolemic and antioxidative effects of tyramine derivatives from the root bark of Lycium chenese Miller. Nutrition research and practice. 2011 Oct; 5(5):412-20. doi: 10.4162/nrp.2011.5.5.412. [PMID: 22125678]
  • Kiyoon Kang, Sangkyu Park, Young Soon Kim, Kyoungwhan Back. Methanol elicits the biosynthesis of 4-coumaroylserotonin and feruloylserotonin in rice seedlings. Plant signaling & behavior. 2011 Jun; 6(6):881-3. doi: 10.4161/psb.6.6.15280. [PMID: 21546791]
  • Kiyoon Kang, Sangkyu Park, Uyanga Natsagdorj, Young Soon Kim, Kyoungwhan Back. Methanol is an endogenous elicitor molecule for the synthesis of tryptophan and tryptophan-derived secondary metabolites upon senescence of detached rice leaves. The Plant journal : for cell and molecular biology. 2011 Apr; 66(2):247-57. doi: 10.1111/j.1365-313x.2011.04486.x. [PMID: 21205035]
  • Sajida Abdureyim, Nurmuhammat Amat, Anwar Umar, Halmurat Upur, Benedicte Berke, Nicholas Moore. Anti-inflammatory, immunomodulatory, and heme oxygenase-1 inhibitory activities of ravan napas, a formulation of uighur traditional medicine, in a rat model of allergic asthma. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):. doi: 10.1155/2011/725926. [PMID: 20953388]
  • Jia-Ming Chang, Le-Mei Hung, Yau-Jan Chyan, Chun-Ming Cheng, Rey-Yuh Wu. Carthamus tinctorius Enhances the Antitumor Activity of Dendritic Cell Vaccines via Polarization toward Th1 Cytokines and Increase of Cytotoxic T Lymphocytes. Evidence-based complementary and alternative medicine : eCAM. 2011; 2011(?):274858. doi: 10.1093/ecam/nen068. [PMID: 19001481]
  • Jang-Yeol Choi, Hyeri Kim, Yeo-Jin Choi, Atsushi Ishihara, Kyoungwhan Back, Seong-Gene Lee. Cytoprotective activities of hydroxycinnamic acid amides of serotonin against oxidative stress-induced damage in HepG2 and HaCaT cells. Fitoterapia. 2010 Dec; 81(8):1134-41. doi: 10.1016/j.fitote.2010.07.015. [PMID: 20655990]
  • Shin-ichiro Katsuda, Katsuya Suzuki, Naoto Koyama, Michio Takahashi, Masao Miyake, Akihiro Hazama, Kenji Takazawa. Safflower seed polyphenols (N-(p-coumaroyl)serotonin and N-feruloylserotonin) ameliorate atherosclerosis and distensibility of the aortic wall in Kurosawa and Kusanagi-hypercholesterolemic (KHC) rabbits. Hypertension research : official journal of the Japanese Society of Hypertension. 2009 Nov; 32(11):944-9. doi: 10.1038/hr.2009.144. [PMID: 19763138]
  • Kiyoon Kang, Sangkyu Park, Young Soon Kim, Sungbeom Lee, Kyoungwhan Back. Biosynthesis and biotechnological production of serotonin derivatives. Applied microbiology and biotechnology. 2009 May; 83(1):27-34. doi: 10.1007/s00253-009-1956-1. [PMID: 19308403]
  • Kiyoon Kang, Kyoungwhan Back. Production of phenylpropanoid amides in recombinant Escherichia coli. Metabolic engineering. 2009 Jan; 11(1):64-8. doi: 10.1016/j.ymben.2008.08.004. [PMID: 18805501]
  • Munyoung Park, Kiyoon Kang, Sangkyu Park, Young Soon Kim, Sun-Hwa Ha, Shin Woo Lee, Mi-Jeong Ahn, Jung-Myung Bae, Kyoungwhan Back. Expression of serotonin derivative synthetic genes on a single self-processing polypeptide and the production of serotonin derivatives in microbes. Applied microbiology and biotechnology. 2008 Nov; 81(1):43-9. doi: 10.1007/s00253-008-1634-8. [PMID: 18709368]
  • Atsushi Ishihara, Yumi Hashimoto, Hisashi Miyagawa, Kyo Wakasa. Induction of serotonin accumulation by feeding of rice striped stem borer in rice leaves. Plant signaling & behavior. 2008 Sep; 3(9):714-6. doi: 10.4161/psb.3.9.6456. [PMID: 19704837]
  • Kyungjin Lee, Kiyoon Kang, Munyoung Park, Young-Min Woo, Kyoungwhan Back. Endosperm-specific expression of serotonin N-hydroxycinnamoyltransferase in rice. Plant foods for human nutrition (Dordrecht, Netherlands). 2008 Jun; 63(2):53-7. doi: 10.1007/s11130-007-0069-1. [PMID: 18213519]
  • Naoto Koyama, Kanna Kuribayashi, Tetsuya Seki, Katsunori Kobayashi, Yasufumi Furuhata, Katsuya Suzuki, Harumi Arisaka, Takashi Nakano, Yusuke Amino, Koichi Ishii. Serotonin derivatives, major safflower (Carthamus tinctorius L.) seed antioxidants, inhibit low-density lipoprotein (LDL) oxidation and atherosclerosis in apolipoprotein E-deficient mice. Journal of agricultural and food chemistry. 2006 Jul; 54(14):4970-6. doi: 10.1021/jf060254p. [PMID: 16819904]
  • Sei Kang, Kiyoon Kang, Gap Chae Chung, Doil Choi, Atsushi Ishihara, Dong-Sun Lee, Kyoungwhan Back. Functional analysis of the amine substrate specificity domain of pepper tyramine and serotonin N-hydroxycinnamoyltransferases. Plant physiology. 2006 Feb; 140(2):704-15. doi: 10.1104/pp.105.071514. [PMID: 16384907]
  • Sun-Mi Jang, Atsushi Ishihara, Kyoungwhan Back. Production of coumaroylserotonin and feruloylserotonin in transgenic rice expressing pepper hydroxycinnamoyl-coenzyme A:serotonin N-(hydroxycinnamoyl)transferase. Plant physiology. 2004 May; 135(1):346-56. doi: 10.1104/pp.103.038372. [PMID: 15122017]
  • Eiji Tanaka, Chihiro Tanaka, Naoki Mori, Yasumasa Kuwahara, Mitsuya Tsuda. Phenylpropanoid amides of serotonin accumulate in witches' broom diseased bamboo. Phytochemistry. 2003 Nov; 64(5):965-9. doi: 10.1016/s0031-9422(03)00429-1. [PMID: 14561512]
  • Y Kumarasamy, M Middleton, R G Reid, L Nahar, S D Sarker. Biological activity of serotonin conjugates from the seeds of Centaurea nigra. Fitoterapia. 2003 Sep; 74(6):609-12. doi: 10.1016/s0367-326x(03)00144-8. [PMID: 12946728]
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