3-Feruloylquinic acid (BioDeep_00000000966)

Main id: BioDeep_00000402901

Secondary id: BioDeep_00000169803, BioDeep_00000229120

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite natural product


代谢物信息卡片


(1S,3R,4R,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid

化学式: C17H20O9 (368.1107)
中文名称:
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 89.39%

分子结构信息

SMILES: c1(cc(c(cc1)O)OC)/C=C/C(=O)O[C@H]1C[C@@](C[C@@H]([C@@H]1O)O)(O)C(=O)O
InChI: InChI=1S/C17H20O9/c1-25-12-6-9(2-4-10(12)18)3-5-14(20)26-13-8-17(24,16(22)23)7-11(19)15(13)21/h2-6,11,13,15,18-19,21,24H,7-8H2,1H3,(H,22,23)/b5-3+/t11-,13-,15-,17+/m0/s1

描述信息

3-Feruloylquinic acid (3-FQA) (CAS: 1899-29-2) belongs to the class of organic compounds known as quinic acids and derivatives. Quinic acids and derivatives are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1. Coffee, especially green or raw coffee, is a major source of chlorogenic acids (CGA). CGAs have been associated with a range of health benefits including a reduction in the risk of cardiovascular disease, diabetes type 2, and Alzheimers disease. Major CGAs in coffee include 3-, 4-, and 5-feruloylquinic acids (PMID: 19022950). 3-FQA has been detected in the plasma and urine of humans who have ingested coffee (PMID: 19460943). 3-FQA is also found in chicory, tomatoes (Lycopersicon esculentum), and sunflowers (Helianthus annuus).
3-O-feruloyl-D-quinic acid is a quinic acid that is the 3-O-feruloyl derivative of D-quinic acid. It has a role as a plant metabolite. It is a quinic acid and an enoate ester. It is functionally related to a (-)-quinic acid and a ferulic acid.
3-O-Feruloylquinic acid is a natural product found in Astragalus onobrychis, Astragalus arguricus, and other organisms with data available.
5-feruloylquinic acid, also known as O-feruloylquinate, belongs to quinic acids and derivatives class of compounds. Those are compounds containing a quinic acid moiety (or a derivative thereof), which is a cyclitol made up of a cyclohexane ring that bears four hydroxyl groups at positions 1,3.4, and 5, as well as a carboxylic acid at position 1. 5-feruloylquinic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 5-feruloylquinic acid can be found in a number of food items such as sweet cherry, apricot, redcurrant, and peach (variety), which makes 5-feruloylquinic acid a potential biomarker for the consumption of these food products. .
3-Feruloylquinic acid, a derivative of quinic acid-bound phenolic acid, shows antioxidant activity. 3-Feruloylquinic acid markedly enhances by high photosynthetically active radiation (PAR) and UV irradiances[1][2].
3-Feruloylquinic acid, a derivative of quinic acid-bound phenolic acid, shows antioxidant activity. 3-Feruloylquinic acid markedly enhances by high photosynthetically active radiation (PAR) and UV irradiances[1][2].

同义名列表

19 个代谢物同义名

(1S,3R,4R,5R)-1,3,4-trihydroxy-5-{[(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}cyclohexane-1-carboxylic acid; (1S,3R,4R,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxycyclohexane-1-carboxylic acid; (1S,3R,4R,5R)-1,3,4-trihydroxy-5-[(E)-3-(4-hydroxy-3-methoxy-phenyl)prop-2-enoyl]oxy-cyclohexanecarboxylic acid; trans-3-O-Feruloyl quinic acid; trans-3-O-Feruloylquinic acid; 5-O-(E)-Feruloylquinic Acid; 3-O-(E)-Feruloylquinic acid; 3-O-feruloyl-D-quinic acid; 5-O-Feruloylquinic acid; 3-O-Feruloylquinic acid; O-Feruloylquinic acid; 3-Feruloylquinic acid; 3-Ferulylquinic acid; 3-O-Feruloylquinate; feruloylquinic acid; 3-Feruloylquinate; O-Feruloylquinate; 3-FQA; 5-Feruloylquinic acid



数据库引用编号

20 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)

133 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 13 ACE, AIMP2, BCL2, CASP9, CGAS, CTNNB1, FGF2, HDAC9, HRAS, NOS3, PTGS2, TYR, XDH
Peripheral membrane protein 2 CGAS, PTGS2
Endoplasmic reticulum membrane 3 BCL2, HRAS, PTGS2
Nucleus 9 AIMP2, BCL2, CASP9, CGAS, CTNNB1, FGF2, HDAC9, NOS3, PPARGC1A
cytosol 10 AIMP2, BCL2, CASP9, CGAS, CTNNB1, HRAS, IL1B, NOS3, PPARGC1A, XDH
nuclear body 1 CGAS
centrosome 1 CTNNB1
nucleoplasm 6 CGAS, CTNNB1, HDAC9, HRAS, NOS3, PPARGC1A
Cell membrane 4 ACE, CGAS, CTNNB1, HRAS
Lipid-anchor 1 HRAS
Cytoplasmic side 1 HRAS
lamellipodium 1 CTNNB1
Golgi apparatus membrane 1 HRAS
Synapse 1 CTNNB1
cell cortex 1 CTNNB1
cell junction 1 CTNNB1
cell surface 1 TNR
glutamatergic synapse 3 CTNNB1, HRAS, TNR
Golgi apparatus 2 HRAS, NOS3
Golgi membrane 3 HRAS, INS, NOS3
lysosomal membrane 1 GAA
presynaptic membrane 1 CTNNB1
Cytoplasm, cytosol 3 AIMP2, CGAS, IL1B
Lysosome 4 ACE, GAA, IL1B, TYR
endosome 1 ACE
plasma membrane 6 ACE, CGAS, CTNNB1, GAA, HRAS, NOS3
Membrane 6 ACE, AIMP2, BCL2, CTNNB1, GAA, HRAS
basolateral plasma membrane 1 CTNNB1
caveola 2 NOS3, PTGS2
extracellular exosome 3 ACE, CTNNB1, GAA
Lysosome membrane 1 GAA
endoplasmic reticulum 2 BCL2, PTGS2
extracellular space 8 ACE, FGF2, GNRH1, IL1B, IL6, INS, TNR, XDH
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 4 CTNNB1, HRAS, NOS3, TYR
Schaffer collateral - CA1 synapse 2 CTNNB1, TNR
adherens junction 1 CTNNB1
apicolateral plasma membrane 1 CTNNB1
bicellular tight junction 1 CTNNB1
mitochondrion 2 BCL2, CASP9
protein-containing complex 4 BCL2, CASP9, CTNNB1, PTGS2
intracellular membrane-bounded organelle 2 GAA, TYR
Microsome membrane 1 PTGS2
Single-pass type I membrane protein 2 ACE, TYR
Secreted 6 ACE, FGF2, GAA, IL1B, IL6, INS
extracellular region 8 ACE, FGF2, GAA, GNRH1, IL1B, IL6, INS, TNR
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
transcription regulator complex 2 CTNNB1, HDAC9
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 ACE
Secreted, extracellular space, extracellular matrix 1 TNR
Z disc 1 CTNNB1
beta-catenin destruction complex 1 CTNNB1
Wnt signalosome 1 CTNNB1
Melanosome membrane 1 TYR
Cytoplasm, P-body 1 NOS3
P-body 1 NOS3
apical part of cell 1 CTNNB1
cell-cell junction 1 CTNNB1
Golgi-associated vesicle 1 TYR
postsynaptic membrane 1 CTNNB1
Membrane raft 1 TNR
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 CTNNB1
focal adhesion 1 CTNNB1
Cell junction, adherens junction 1 CTNNB1
flotillin complex 1 CTNNB1
Peroxisome 1 XDH
sarcoplasmic reticulum 1 XDH
Nucleus, PML body 1 PPARGC1A
PML body 1 PPARGC1A
collagen-containing extracellular matrix 1 TNR
secretory granule 1 IL1B
fascia adherens 1 CTNNB1
lateral plasma membrane 1 CTNNB1
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
neuron projection 1 PTGS2
chromatin 1 PPARGC1A
cell periphery 1 CTNNB1
Chromosome 1 CGAS
cytoskeleton 1 NOS3
Cytoplasm, cytoskeleton, cilium basal body 1 CTNNB1
brush border membrane 1 ACE
spindle pole 1 CTNNB1
sperm midpiece 1 ACE
postsynaptic density, intracellular component 1 CTNNB1
microvillus membrane 1 CTNNB1
site of double-strand break 1 CGAS
Endomembrane system 2 CTNNB1, HRAS
endosome lumen 1 INS
tertiary granule membrane 1 GAA
Melanosome 1 TYR
Cytoplasm, Stress granule 1 NOS3
cytoplasmic stress granule 1 NOS3
euchromatin 1 CTNNB1
myelin sheath 1 BCL2
basal plasma membrane 1 ACE
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 IL6, INS, PTGS2
histone methyltransferase complex 1 HDAC9
endocytic vesicle membrane 1 NOS3
histone deacetylase complex 1 HDAC9
transport vesicle 1 INS
azurophil granule membrane 1 GAA
beta-catenin-TCF complex 1 CTNNB1
Secreted, extracellular exosome 1 IL1B
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
perineuronal net 1 TNR
apoptosome 1 CASP9
presynaptic active zone cytoplasmic component 1 CTNNB1
[Isoform 1]: Nucleus 1 PPARGC1A
protein-DNA complex 1 CTNNB1
ficolin-1-rich granule membrane 1 GAA
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
catenin complex 1 CTNNB1
GTPase complex 1 HRAS
interleukin-6 receptor complex 1 IL6
autolysosome lumen 1 GAA
BAD-BCL-2 complex 1 BCL2
[Angiotensin-converting enzyme, soluble form]: Secreted 1 ACE
[Isoform Testis-specific]: Cell membrane 1 ACE
beta-catenin-TCF7L2 complex 1 CTNNB1
tenascin complex 1 TNR
beta-catenin-ICAT complex 1 CTNNB1
Scrib-APC-beta-catenin complex 1 CTNNB1
caspase complex 1 CASP9
[Isoform B4]: Nucleus 1 PPARGC1A
[Isoform B4-8a]: Cytoplasm 1 PPARGC1A
[Isoform B5]: Nucleus 1 PPARGC1A
[Isoform 9]: Nucleus 1 PPARGC1A


文献列表

  • Duy Thanh Nguyen, Jamila Iqbal, Jianying Han, Gregory K Pierens, Stephen A Wood, George D Mellick, Yunjiang Feng. Chemical constituents from Macleaya cordata (Willd) R. Br. and their phenotypic functions against a Parkinson's disease patient-derived cell line. Bioorganic & medicinal chemistry. 2020 11; 28(21):115732. doi: 10.1016/j.bmc.2020.115732. [PMID: 33065438]