3,4-Dihydroxyhydrocinnamic acid (BioDeep_00000396444)

Main id: BioDeep_00000003369

 

human metabolite PANOMIX_OTCML-2023 blood metabolite


代谢物信息卡片


InChI=1/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13

化学式: C9H10O4 (182.0579)
中文名称: 3,4-二羟苯基丙酸, 3,4-二羟基苯基丙酸, 二氢咖啡酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: c1(c(ccc(c1)CCC(=O)O)O)O
InChI: InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)

描述信息

3,4-Dihydroxyhydrocinnamic acid, also known as dihydrocaffeic acid (DHCA), is a metabolite product of the hydrogenation of caffeoylquinic acids, occurring in normal human biofluids, with potent antioxidant properties. DHCA has been detected in human plasma following coffee ingestion (PMID: 15607645) and is increased with some dietary sources, such as after ingestion of phenolic constituents of artichoke leaf extract (PMID: 15693705). Polyphenol-rich foods such as vegetables and fruits have been shown to significantly improve platelet function in ex vivo studies in humans (PMID: 16038718). Its antioxidant activity has been tested to reduce ferric iron in the ferric reducing antioxidant power (FRAP) assay, and it has been suggested that its catechol structure conveys the antioxidant effect in plasma and in erythrocytes (PMID: 11768243). 3,4-Dihydroxyhydrocinnamic acid is a microbial metabolite found in Bifidobacterium, Escherichia, Lactobacillus, and Clostridium (PMID: 28393285).
3,4-Dihydroxyhydrocinnamic acid (or Dihydrocaffeic acid, DHCA) is a metabolite product of the hydrogenation of caffeoylquinic acids, occurring in normal human biofluids, with potent antioxidant properties. DHCA has been detected in human plasma following coffee ingestion (PMID 15607645), and is increased with some dietary sources, such as after ingestion of phenolic constituents of artichoke leaf extract. (PMID 15693705) Polyphenol-rich foods such as vegetables and fruits have been shown to significantly improve platelet function in ex vivo studies in humans. (PMID 16038718) Its antioxidant activity has been tested to reduce ferric iron in the ferric reducing antioxidant power (FRAP) assay, and it has been suggested that its catechol structure convey the antioxidant effect in plasma and in erythrocytes. (PMID 11768243) [HMDB]. 3-(3,4-Dihydroxyphenyl)propanoic acid is found in red beetroot, common beet, and olive.
3-(3,4-dihydroxyphenyl)propanoic acid is a monocarboxylic acid that is 3-phenylpropionic acid substituted by hydroxy groups at positions 3 and 4. Also known as dihydrocaffeic acid, it is a metabolite of caffeic acid and exhibits antioxidant activity. It has a role as an antioxidant and a human xenobiotic metabolite. It is functionally related to a 3-phenylpropionic acid. It is a conjugate acid of a 3-(3,4-dihydroxyphenyl)propanoate.
3-(3,4-Dihydroxyphenyl)propionic acid is a natural product found in Liatris elegans, Polyscias murrayi, and other organisms with data available.
Dihydrocaffeic acid is a microbial metabolite of flavonoids, reduces phosphorylation of MAPK p38 and prevent UVB-induced skin damage. Antioxidant potential and anti-inflammatory activity[1].
Dihydrocaffeic acid is a microbial metabolite of flavonoids, reduces phosphorylation of MAPK p38 and prevent UVB-induced skin damage. Antioxidant potential and anti-inflammatory activity[1].

同义名列表

48 个代谢物同义名

InChI=1/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13; 3,4-dihydroxyphenylpropionic acid, potassium salt; 3,4-dihydroxy-(6CI,7CI,8CI)Hydrocinnamic acid; 3-10-00-01517 (Beilstein Handbook Reference); 3-[3,4-bis(oxidanyl)phenyl]propanoic acid; 3,4-dihydroxy-(6CI,7CI,8CI)Hydrocinnamate; 3,4-DIHYDROXY-.BETA.-PHENYLPROPIONIC ACID; 3,4-Dihydroxy-beta-phenylpropionic acid; 3-(3,4-Dihydroxyphenyl)propanoic acid #; 3-(3,4-dihydroxyphenyl) propionic acid; 3,4-Dihydroxyhydrocinnamic acid, 98\\%; Benzenepropanoic acid, 3,4-dihydroxy-; 3-(3,4-Dihydroxyphenyl)propanoic acid; 3-(3,4-Dihydroxyphenyl)propionic acid; BF0C7A6D-A5FC-4B39-819E-5ECC037C0C39; 3,4-Dihydroxy-β-phenylpropionic acid; 3,4-Dihydroxy-b-phenylpropionic acid; 3-(3,4-DIHYDROXYPHENYL)PROPIONICACID; 3,4-Dihydroxy-beta-phenylpropionate; 3,4-Dihydroxy-benzenepropanoic acid; 3,4-Dihydroxybenzenepropanoic acid; Hydrocinnamic acid, 3,4-dihydroxy-; 3,4-Dihydroxybenzenepropionic acid; 3,4-dihydroxyphenylpropionic acid; 3-(3,4-dihydroxyphenyl)propanoate; 3-(3,4-Dihydroxyphenyl)propionate; 3,4-Dihydroxydihydrocinnamic acid; 3,4-dihydroxyhydro cinnamic acid; 3,4-Dihydroxy-β-phenylpropionate; 3,4-Dihydroxy-b-phenylpropionate; Hydrocinnamic acid,4-dihydroxy-; 3,4-dihydroxyhydrocinnamic acid; 3,4-Dihydroxybenzenepropanoate; 3,4-Dihydroxybenzenepropionate; 3,4-Dihydroxydihydrocinnamate; 3,4-Dihydroxyphenylpropionate; 3,4-Dihydroxyphenylpropanoate; 3,4-dihydroxyhydrocinnamate; Dihydrocaffeic acid; Hydrocaffeic acid; Dihydrocaffeate; Dihydrocafeate; Hydrocaffeate; 3,4-HPA; HYKOP; DHC; 3,4-Dihydroxyphenylpropanoate; 3,4-Dihydroxyhydrocinnamic acid



数据库引用编号

19 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

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)

9 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。

亚细胞结构定位 关联基因列表
Cytoplasm 8 ATP2B2, CALCA, CAT, MMP3, NOS3, PFDN5, TYR, XDH
Peripheral membrane protein 1 CYP1B1
Endoplasmic reticulum membrane 1 CYP1B1
Nucleus 5 DNMT1, MMP3, NOS3, PFDN5, SOX9
cytosol 7 CAT, IL1B, LIPE, MMP3, NOS3, PFDN5, XDH
nucleoplasm 3 DNMT1, NOS3, SOX9
Cell membrane 4 ATP2B2, LIPE, SELP, TNF
Multi-pass membrane protein 1 ATP2B2
Synapse 2 ACAN, ATP2B2
cell surface 1 TNF
glutamatergic synapse 2 ACAN, ATP2B2
Golgi apparatus 1 NOS3
Golgi membrane 2 INS, NOS3
neuronal cell body 2 CALCA, TNF
Cytoplasm, cytosol 2 IL1B, LIPE
Lysosome 2 IL1B, TYR
plasma membrane 4 ATP2B2, NOS3, SELP, TNF
terminal bouton 1 CALCA
Membrane 5 ATP2B2, CAT, CYP1B1, LIPE, MMP13
apical plasma membrane 1 ATP2B2
basolateral plasma membrane 1 ATP2B2
caveola 3 ATP2B2, LIPE, NOS3
extracellular exosome 3 ATP2B2, CAT, SELP
extracellular space 11 ACAN, CALCA, IL1B, IL6, INS, MMP1, MMP13, MMP3, SELP, TNF, XDH
lysosomal lumen 1 ACAN
perinuclear region of cytoplasm 2 NOS3, TYR
mitochondrion 4 CAT, CYP1B1, DNMT1, MMP3
protein-containing complex 3 ATP2B2, CAT, SOX9
intracellular membrane-bounded organelle 4 ATP2B2, CAT, CYP1B1, TYR
Microsome membrane 1 CYP1B1
pericentric heterochromatin 1 DNMT1
Single-pass type I membrane protein 2 SELP, TYR
Secreted 7 CALCA, IL1B, IL6, INS, MMP13, MMP3, SELP
extracellular region 11 ACAN, CALCA, CAT, IL1B, IL6, INS, MMP1, MMP13, MMP3, SELP, TNF
hippocampal mossy fiber to CA3 synapse 1 CALCA
neuronal cell body membrane 1 ATP2B2
mitochondrial matrix 1 CAT
transcription regulator complex 1 SOX9
external side of plasma membrane 2 SELP, TNF
Secreted, extracellular space, extracellular matrix 3 ACAN, MMP1, MMP13
T-tubule 1 ATP2B2
Z disc 1 ATP2B2
Melanosome membrane 1 TYR
Cytoplasm, P-body 1 NOS3
P-body 1 NOS3
Golgi-associated vesicle 1 TYR
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
presynaptic active zone membrane 1 ATP2B2
Membrane raft 2 ATP2B2, TNF
focal adhesion 1 CAT
GABA-ergic synapse 2 ACAN, ATP2B2
extracellular matrix 3 MMP1, MMP13, MMP3
Peroxisome 2 CAT, XDH
basement membrane 1 ACAN
sarcoplasmic reticulum 1 XDH
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 1 ACAN
secretory granule 1 IL1B
chromatin 1 SOX9
phagocytic cup 1 TNF
cytoskeleton 1 NOS3
Basolateral cell membrane 1 ATP2B2
sperm flagellum 1 ATP2B2
endosome lumen 1 INS
Lipid droplet 1 LIPE
Membrane, caveola 1 LIPE
Cell projection, cilium, flagellum membrane 1 ATP2B2
female germ cell nucleus 1 DNMT1
Melanosome 1 TYR
Cytoplasm, Stress granule 1 NOS3
cytoplasmic stress granule 1 NOS3
replication fork 1 DNMT1
intermediate filament cytoskeleton 1 PFDN5
platelet dense granule membrane 1 SELP
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 2 CAT, INS
Golgi lumen 2 ACAN, INS
endoplasmic reticulum lumen 2 IL6, INS
endocytic vesicle membrane 1 NOS3
transport vesicle 1 INS
Secreted, extracellular exosome 1 IL1B
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
postsynaptic density membrane 1 ATP2B2
perineuronal net 1 ACAN
neuronal dense core vesicle 1 CALCA
parallel fiber to Purkinje cell synapse 1 ATP2B2
prefoldin complex 1 PFDN5
platelet alpha granule membrane 1 SELP
sperm principal piece 1 ATP2B2
dendritic spine membrane 1 ATP2B2
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
platelet dense granule lumen 1 SELP
catalase complex 1 CAT
interleukin-6 receptor complex 1 IL6
perisynaptic extracellular matrix 1 ACAN
[Isoform WA]: Apical cell membrane 1 ATP2B2
[Isoform WB]: Apical cell membrane 1 ATP2B2
[Isoform XB]: Basolateral cell membrane 1 ATP2B2
[Isoform ZA]: Basolateral cell membrane 1 ATP2B2
[Isoform ZB]: Basolateral cell membrane 1 ATP2B2
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • David S Goldstein, Patti Sullivan, Abraham Corrales, Risa Isonaka, Janna Gelsomino, Jamie Cherup, Genessis Castillo, Courtney Holmes. Multiple catechols in human plasma after drinking caffeinated or decaffeinated coffee. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2021 Nov; 1185(?):122988. doi: 10.1016/j.jchromb.2021.122988. [PMID: 34731744]
  • Maizatul Hasyima Omar, Rocío González Barrio, Gema Pereira-Caro, Tahani Mazyad Almutairi, Alan Crozier. In vitro catabolism of 3',4'-dihydroxycinnamic acid by human colonic microbiota. International journal of food sciences and nutrition. 2021 Jun; 72(4):511-517. doi: 10.1080/09637486.2020.1850650. [PMID: 33238790]
  • Nils Mertens, Thomas Heymann, Marcus A Glomb. Oxidative Fragmentation of Aspalathin Leads to the Formation of Dihydrocaffeic Acid and the Related Lysine Amide Adduct. Journal of agricultural and food chemistry. 2020 Nov; 68(46):13111-13120. doi: 10.1021/acs.jafc.9b07689. [PMID: 32023062]
  • Shenli Wang, Beatriz Sarriá, Raquel Mateos, Luis Goya, Laura Bravo-Clemente. TNF-α-induced oxidative stress and endothelial dysfunction in EA.hy926 cells is prevented by mate and green coffee extracts, 5-caffeoylquinic acid and its microbial metabolite, dihydrocaffeic acid. International journal of food sciences and nutrition. 2019 May; 70(3):267-284. doi: 10.1080/09637486.2018.1505834. [PMID: 30185085]
  • Mariana M Oliveira, Bianca A Ratti, Regina G Daré, Sueli O Silva, Maria da Conceição T Truiti, Tânia Ueda-Nakamura, Rachel Auzély-Velty, Celso V Nakamura. Dihydrocaffeic Acid Prevents UVB-Induced Oxidative Stress Leading to the Inhibition of Apoptosis and MMP-1 Expression via p38 Signaling Pathway. Oxidative medicine and cellular longevity. 2019; 2019(?):2419096. doi: 10.1155/2019/2419096. [PMID: 30800206]
  • Gema Baeza, Eva-Maria Bachmair, Sharon Wood, Raquel Mateos, Laura Bravo, Baukje de Roos. The colonic metabolites dihydrocaffeic acid and dihydroferulic acid are more effective inhibitors of in vitro platelet activation than their phenolic precursors. Food & function. 2017 Mar; 8(3):1333-1342. doi: 10.1039/c6fo01404f. [PMID: 28229135]
  • Siyu Wang, Joon Hyuk Suh, Xi Zheng, Yu Wang, Chi-Tang Ho. Identification and Quantification of Potential Anti-inflammatory Hydroxycinnamic Acid Amides from Wolfberry. Journal of agricultural and food chemistry. 2017 Jan; 65(2):364-372. doi: 10.1021/acs.jafc.6b05136. [PMID: 28008757]
  • Pei Wang, Huadong Chen, Yingdong Zhu, Jennifer McBride, Junsheng Fu, Shengmin Sang. Oat avenanthramide-C (2c) is biotransformed by mice and the human microbiota into bioactive metabolites. The Journal of nutrition. 2015 Feb; 145(2):239-45. doi: 10.3945/jn.114.206508. [PMID: 25644343]
  • Felix Aladedunye, Roman Przybylski. Phosphatidylcholine and dihydrocaffeic acid amide mixture enhanced the thermo-oxidative stability of canola oil. Food chemistry. 2014 May; 150(?):494-9. doi: 10.1016/j.foodchem.2013.10.165. [PMID: 24360481]
  • Aya Fujimoto, Miyuki Inai, Toshiya Masuda. Chemical evidence for the synergistic effect of a cysteinyl thiol on the antioxidant activity of caffeic and dihydrocaffeic esters. Food chemistry. 2013 Jun; 138(2-3):1483-92. doi: 10.1016/j.foodchem.2012.11.073. [PMID: 23411271]
  • Seon-Yeong Kwak, Jin-Kyoung Yang, Hye-Ryung Choi, Kyung-Chan Park, Young-Bu Kim, Yoon-Sik Lee. Synthesis and dual biological effects of hydroxycinnamoyl phenylalanyl/prolyl hydroxamic acid derivatives as tyrosinase inhibitor and antioxidant. Bioorganic & medicinal chemistry letters. 2013 Feb; 23(4):1136-42. doi: 10.1016/j.bmcl.2012.10.107. [PMID: 23305921]
  • Toshiya Masuda, Miyuki Inai, Yukari Miura, Akiko Masuda, Satoshi Yamauchi. Effect of polyphenols on oxymyoglobin oxidation: prooxidant activity of polyphenols in vitro and inhibition by amino acids. Journal of agricultural and food chemistry. 2013 Feb; 61(5):1097-104. doi: 10.1021/jf304775x. [PMID: 23311772]
  • Kuan-Chung Chen, Su-Sen Chang, Fuu-Jen Tsai, Calvin Yu-Chian Chen. Han ethnicity-specific type 2 diabetic treatment from traditional Chinese medicine?. Journal of biomolecular structure & dynamics. 2013; 31(11):1219-35. doi: 10.1080/07391102.2012.732340. [PMID: 23146021]
  • Piotr Duchnowicz, Marlena Broncel, Anna Podsędek, Maria Koter-Michalak. Hypolipidemic and antioxidant effects of hydroxycinnamic acids, quercetin, and cyanidin 3-glucoside in hypercholesterolemic erythrocytes (in vitro study). European journal of nutrition. 2012 Jun; 51(4):435-43. doi: 10.1007/s00394-011-0227-y. [PMID: 21755326]
  • Kathleen Trautwein, Heinz Wilkes, Ralf Rabus. Proteogenomic evidence for β-oxidation of plant-derived 3-phenylpropanoids in "Aromatoleum aromaticum" EbN1. Proteomics. 2012 May; 12(9):1402-13. doi: 10.1002/pmic.201100279. [PMID: 22589189]
  • Raja S Payyavula, Duroy A Navarre, Joseph C Kuhl, Alberto Pantoja, Syamkumar S Pillai. Differential effects of environment on potato phenylpropanoid and carotenoid expression. BMC plant biology. 2012 Mar; 12(?):39. doi: 10.1186/1471-2229-12-39. [PMID: 22429339]
  • Zuzana Kyselova. Toxicological aspects of the use of phenolic compounds in disease prevention. Interdisciplinary toxicology. 2011 Dec; 4(4):173-83. doi: 10.2478/v10102-011-0027-5. [PMID: 22319251]
  • Reina Aoki, Tatsurou Yagami, Hiroyuki Sasakura, Ken-Ichi Ogura, Yasuhiro Kajihara, Masakazu Ibi, Takeaki Miyamae, Fumio Nakamura, Taro Asakura, Yoshikatsu Kanai, Yoshimi Misu, Yuichi Iino, Marina Ezcurra, William R Schafer, Ikue Mori, Yoshio Goshima. A seven-transmembrane receptor that mediates avoidance response to dihydrocaffeic acid, a water-soluble repellent in Caenorhabditis elegans. The Journal of neuroscience : the official journal of the Society for Neuroscience. 2011 Nov; 31(46):16603-10. doi: 10.1523/jneurosci.4018-11.2011. [PMID: 22090488]
  • Karine Redeuil, Candice Smarrito-Menozzi, Philippe Guy, Serge Rezzi, Fabiola Dionisi, Gary Williamson, Kornél Nagy, Mathieu Renouf. Identification of novel circulating coffee metabolites in human plasma by liquid chromatography-mass spectrometry. Journal of chromatography. A. 2011 Jul; 1218(29):4678-88. doi: 10.1016/j.chroma.2011.05.050. [PMID: 21676405]
  • Annett Braune, Michael Blaut. Deglycosylation of puerarin and other aromatic C-glucosides by a newly isolated human intestinal bacterium. Environmental microbiology. 2011 Feb; 13(2):482-94. doi: 10.1111/j.1462-2920.2010.02352.x. [PMID: 20946528]
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