sinapyl alcohol (BioDeep_00000406289)

Main id: BioDeep_00000003275

 

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


sinapyl alcohol

化学式: C11H14O4 (210.0892)
中文名称: 芥子醇
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: COC1=CC(=CC(=C1O)OC)C=CCO
InChI: InChI=1S/C11H14O4/c1-14-9-6-8(4-3-5-12)7-10(15-2)11(9)13/h3-4,6-7,12-13H,5H2,1-2H3

描述信息

A primary alcohol, being cinnamyl alcohol hydroxylated at C-4 and methoxylated at C-3 and -5.
Sinapyl alcohol, also known as 4-(3-hydroxy-1-propenyl)-2,6-dimethoxy-phenol or 4-hydroxy-3,5-dimethoxycinnamyl alcohol, is a member of the class of compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Sinapyl alcohol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Sinapyl alcohol can be found in a number of food items such as ginseng, endive, sea-buckthornberry, and white cabbage, which makes sinapyl alcohol a potential biomarker for the consumption of these food products. Sinapyl alcohol is an organic compound structurally related to cinnamic acid. It is biosynthetized via the phenylpropanoid biochemical pathway, its immediate precursor being sinapaldehyde. This phytochemical is one of the monolignols, which are precursor to lignin or lignans. It is also a biosynthetic precursor to various stilbenoids and coumarins .

同义名列表

3 个代谢物同义名

sinapyl alcohol; Sinapyl-alcohol; Sinapyl alcohol



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(2)

PlantCyc(2)

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)

42 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 11 ALB, APEH, CAT, CCR2, DHPS, HGS, LST1, MSMP, NOS2, PRX, ZNF346
Peripheral membrane protein 4 ACHE, CYP1B1, HGS, PRX
Endoplasmic reticulum membrane 2 CYP1B1, POR
Nucleus 6 ACHE, ALB, MYB, NOS2, PRX, ZNF346
cytosol 11 ALB, APEH, CAT, CBL, COMT, DHPS, HGS, LST1, MYB, NOS2, POR
dendrite 2 CCR2, COMT
centrosome 1 ALB
nucleoplasm 3 MYB, NOS2, ZNF346
RNA polymerase II transcription regulator complex 1 MYB
Cell membrane 5 ACHE, CCR2, COMT, PRX, TNF
Cytoplasmic side 3 HGS, POR, PRX
Early endosome membrane 1 HGS
Multi-pass membrane protein 2 CCR2, LST1
Synapse 2 ACHE, COMT
cell junction 1 PRX
cell surface 2 ACHE, TNF
Golgi apparatus 4 ACHE, ALB, CBL, LST1
Golgi membrane 1 LST1
growth cone 1 CBL
lysosomal membrane 1 CP
neuromuscular junction 1 ACHE
neuronal cell body 2 CCR2, TNF
Cytoplasm, cytosol 1 NOS2
Lysosome 1 HGS
endosome 1 HGS
plasma membrane 10 ACHE, BCHE, CBL, CCR2, COMT, CP, LST1, NOS2, PRX, TNF
Membrane 8 ACHE, CAT, CCR2, COMT, CYP1B1, LST1, MYB, POR
axon 1 COMT
basolateral plasma membrane 1 LST1
extracellular exosome 6 ALB, APEH, CAT, COMT, CP, HGS
endoplasmic reticulum 2 ALB, POR
extracellular space 6 ACHE, ALB, BCHE, CP, MSMP, TNF
perinuclear region of cytoplasm 4 ACHE, CBL, CCR2, NOS2
mitochondrion 2 CAT, CYP1B1
protein-containing complex 2 ALB, CAT
intracellular membrane-bounded organelle 4 CAT, COMT, CYP1B1, POR
Microsome membrane 1 CYP1B1
Secreted 5 ACHE, ALB, BCHE, CP, MSMP
extracellular region 7 ACHE, ALB, APEH, BCHE, CAT, CP, TNF
Single-pass membrane protein 1 POR
mitochondrial matrix 1 CAT
Extracellular side 2 ACHE, COMT
anchoring junction 2 ALB, PRX
Cell projection, cilium 1 CBL
nuclear membrane 1 APEH
external side of plasma membrane 2 CCR2, TNF
perikaryon 1 CCR2
nucleolus 1 ZNF346
Cytoplasm, P-body 1 NOS2
P-body 1 NOS2
Early endosome 1 HGS
recycling endosome 1 TNF
Single-pass type II membrane protein 2 COMT, TNF
Cytoplasm, perinuclear region 1 NOS2
Membrane raft 2 CBL, TNF
focal adhesion 2 CAT, CBL
flotillin complex 1 CBL
Peroxisome 2 CAT, NOS2
basement membrane 1 ACHE
Peroxisome matrix 1 CAT
peroxisomal matrix 2 CAT, NOS2
peroxisomal membrane 1 CAT
ciliary basal body 1 ALB
cilium 1 CBL
phagocytic cup 1 TNF
centriole 1 ALB
Nucleus, nucleolus 1 ZNF346
spindle pole 1 ALB
blood microparticle 3 ALB, BCHE, CP
Basolateral cell membrane 1 LST1
Lipid-anchor, GPI-anchor 1 ACHE
fibrillar center 1 CCR2
side of membrane 1 ACHE
basal plasma membrane 1 LST1
multivesicular body membrane 1 HGS
ficolin-1-rich granule lumen 2 APEH, CAT
secretory granule lumen 1 CAT
endoplasmic reticulum lumen 3 ALB, BCHE, CP
nuclear matrix 1 MYB
platelet alpha granule lumen 1 ALB
nuclear envelope lumen 1 BCHE
[Isoform 2]: Cytoplasm 1 PRX
Endosome, multivesicular body membrane 1 HGS
ESCRT-0 complex 1 HGS
phagocytic vesicle lumen 1 HGS
synaptic cleft 1 ACHE
Basal cell membrane 1 LST1
[Isoform 1]: Cell membrane 1 PRX
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
cortical cytoskeleton 1 NOS2
catalase complex 1 CAT
[Isoform Soluble]: Cytoplasm 1 COMT
[Isoform Membrane-bound]: Cell membrane 1 COMT
[Isoform H]: Cell membrane 1 ACHE
ciliary transition fiber 1 ALB
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Fan Wang, Wanli Zhao, Wei Lv, Pirui Li, Mei Tian, Shu Xu, Linwei Li, Ruiyang Wang, Fei Liu, Yu Chen, Xu Feng. Identification and Functional Characterization of a Novel Sinapyl Alcohol Acyltransferase from Euphorbia lathyris L. Journal of agricultural and food chemistry. 2023 Dec; 71(50):20187-20197. doi: 10.1021/acs.jafc.3c07127. [PMID: 38044624]
  • Junying Ma, Xiaoyan Li, Maolin He, Yanwen Li, Wei Lu, Mengyao Li, Bo Sun, Yangxia Zheng. A Joint Transcriptomic and Metabolomic Analysis Reveals the Regulation of Shading on Lignin Biosynthesis in Asparagus. International journal of molecular sciences. 2023 Jan; 24(2):. doi: 10.3390/ijms24021539. [PMID: 36675053]
  • Bin Wang, Zhicheng Li, Zhanhong Han, Sulin Xue, Yang Bi, Dov Prusky. Effects of nitric oxide treatment on lignin biosynthesis and texture properties at wound sites of muskmelons. Food chemistry. 2021 Nov; 362(?):130193. doi: 10.1016/j.foodchem.2021.130193. [PMID: 34082290]
  • Clémence Simon, Cédric Lion, Hania Ahouari, Hervé Vezin, Simon Hawkins, Christophe Biot. EPR imaging of sinapyl alcohol and its application to the study of plant cell wall lignification. Chemical communications (Cambridge, England). 2021 Jan; 57(3):387-390. doi: 10.1039/d0cc05218c. [PMID: 33326527]
  • Eric M Anderson, Michael L Stone, Rui Katahira, Michelle Reed, Wellington Muchero, Kelsey J Ramirez, Gregg T Beckham, Yuriy Román-Leshkov. Differences in S/G ratio in natural poplar variants do not predict catalytic depolymerization monomer yields. Nature communications. 2019 05; 10(1):2033. doi: 10.1038/s41467-019-09986-1. [PMID: 31048697]
  • Jun Shigeto, Yukie Ueda, Shinya Sasaki, Koki Fujita, Yuji Tsutsumi. Enzymatic activities for lignin monomer intermediates highlight the biosynthetic pathway of syringyl monomers in Robinia pseudoacacia. Journal of plant research. 2017 Jan; 130(1):203-210. doi: 10.1007/s10265-016-0882-4. [PMID: 27888422]
  • Amandeep K Sangha, Loukas Petridis, Xiaolin Cheng, Jeremy C Smith. Relative Binding Affinities of Monolignols to Horseradish Peroxidase. The journal of physical chemistry. B. 2016 08; 120(31):7635-40. doi: 10.1021/acs.jpcb.6b00789. [PMID: 27447548]
  • Yuanheng Cai, Mohammad-Wadud Bhuiya, John Shanklin, Chang-Jun Liu. Engineering a monolignol 4-O-methyltransferase with high selectivity for the condensed lignin precursor coniferyl alcohol. The Journal of biological chemistry. 2015 Oct; 290(44):26715-24. doi: 10.1074/jbc.m115.684217. [PMID: 26378240]
  • Yuki Tobimatsu, Armin Wagner, Lloyd Donaldson, Prajakta Mitra, Claudiu Niculaes, Oana Dima, Jeong Im Kim, Nickolas Anderson, Dominique Loque, Wout Boerjan, Clint Chapple, John Ralph. Visualization of plant cell wall lignification using fluorescence-tagged monolignols. The Plant journal : for cell and molecular biology. 2013 Nov; 76(3):357-66. doi: 10.1111/tpj.12299. [PMID: 23889038]
  • Xinhui Tian, Gang Ding, Chaozhong Peng, Yanbao Hu, Li Li, Hong Chen, Zhongmei Zou. Sinapyl alcohol derivatives from the lipo-soluble part of Dichrocephala benthamii C. B. Clarke. Molecules (Basel, Switzerland). 2013 Jan; 18(2):1720-7. doi: 10.3390/molecules18021720. [PMID: 23434858]
  • Lorena Palacio, Juan J Cantero, Rosa M Cusidó, Marta E Goleniowski. Phenolic compound production in relation to differentiation in cell and tissue cultures of Larrea divaricata (Cav.). Plant science : an international journal of experimental plant biology. 2012 Sep; 193-194(?):1-7. doi: 10.1016/j.plantsci.2012.05.007. [PMID: 22794913]
  • Rocío Santiago, Borja Alarcón, Roberto de Armas, Carlos Vicente, María Estrella Legaz. Changes in cinnamyl alcohol dehydrogenase activities from sugarcane cultivars inoculated with Sporisorium scitamineum sporidia. Physiologia plantarum. 2012 Jun; 145(2):245-59. doi: 10.1111/j.1399-3054.2012.01577.x. [PMID: 22248248]
  • Teresa Martínez-Cortés, Federico Pomar, José Manuel Espiñeira, Fuencisla Merino, Esther Novo-Uzal. Purification and kinetic characterization of two peroxidases of Selaginella martensii Spring. involved in lignification. Plant physiology and biochemistry : PPB. 2012 Mar; 52(?):130-9. doi: 10.1016/j.plaphy.2011.12.008. [PMID: 22305076]
  • Hsi-Chuan Chen, Quanzi Li, Christopher M Shuford, Jie Liu, David C Muddiman, Ronald R Sederoff, Vincent L Chiang. Membrane protein complexes catalyze both 4- and 3-hydroxylation of cinnamic acid derivatives in monolignol biosynthesis. Proceedings of the National Academy of Sciences of the United States of America. 2011 Dec; 108(52):21253-8. doi: 10.1073/pnas.1116416109. [PMID: 22160716]
  • Le Thanh Mai Pham, Su Jin Kim, Bong Keun Song, Yong Hwan Kim. Optimized refolding and characterization of S-peroxidase (CWPO_C of Populus alba) expressed in E. coli. Protein expression and purification. 2011 Dec; 80(2):268-73. doi: 10.1016/j.pep.2011.08.003. [PMID: 21856428]
  • Ahmed M A Abd El-Mawla, Salwa F Farag, Till Beuerle. Cinnamyl alcohols and methyl esters of fatty acids from Wedelia prostrata callus cultures. Natural product research. 2011 Jan; 25(1):45-52. doi: 10.1080/14786419.2010.482937. [PMID: 21240761]
  • Nathalie Demont-Caulet, Catherine Lapierre, Lise Jouanin, Stéphanie Baumberger, Valérie Méchin. Arabidopsis peroxidase-catalyzed copolymerization of coniferyl and sinapyl alcohols: kinetics of an endwise process. Phytochemistry. 2010 Oct; 71(14-15):1673-83. doi: 10.1016/j.phytochem.2010.06.011. [PMID: 20615517]
  • Esther Novo Uzal, Laura V Gómez Ros, Federico Pomar, María A Bernal, Alberto Paradela, Juan P Albar, Alfonso Ros Barceló. The presence of sinapyl lignin in Ginkgo biloba cell cultures changes our views of the evolution of lignin biosynthesis. Physiologia plantarum. 2009 Feb; 135(2):196-213. doi: 10.1111/j.1399-3054.2008.01185.x. [PMID: 19055540]
  • Ronald Hatfield, John Ralph, John H Grabber. A potential role for sinapyl p-coumarate as a radical transfer mechanism in grass lignin formation. Planta. 2008 Nov; 228(6):919-28. doi: 10.1007/s00425-008-0791-4. [PMID: 18654797]
  • Laura V Gómez Ros, Ginés J Aznar-Asensio, Jose A Hernandez, Maria A Bernal, María J L Núñez-Flores, Juan Cuello, Alfonso Ros Barceló. Structural motifs of syringyl peroxidases are conserved during angiosperm evolution. Journal of agricultural and food chemistry. 2007 May; 55(10):4131-8. doi: 10.1021/jf063164t. [PMID: 17439232]
  • Aymerick Eudes, Brigitte Pollet, Richard Sibout, Cao-Trung Do, Armand Séguin, Catherine Lapierre, Lise Jouanin. Evidence for a role of AtCAD 1 in lignification of elongating stems of Arabidopsis thaliana. Planta. 2006 Dec; 225(1):23-39. doi: 10.1007/s00425-006-0326-9. [PMID: 16832689]
  • Yasushi Sato, Ross W Whetten. Characterization of two laccases of loblolly pine (Pinus taeda) expressed in tobacco BY-2 cells. Journal of plant research. 2006 Nov; 119(6):581-8. doi: 10.1007/s10265-006-0020-9. [PMID: 16952031]
  • Carlos Gabaldón, Matías López-Serrano, Federico Pomar, Fuencisla Merino, Juan Cuello, M A Pedreño, A Ros Barceló. Characterization of the last step of lignin biosynthesis in Zinnia elegans suspension cell cultures. FEBS letters. 2006 Aug; 580(18):4311-6. doi: 10.1016/j.febslet.2006.06.088. [PMID: 16842784]
  • Hong Bin Zou, Sheng Yi Dong, Chang Xin Zhou, Li Hong Hu, Yi Hang Wu, Hai Bo Li, Jing Xu Gong, Lian Li Sun, Xiu Mei Wu, Hua Bai, Bo Tao Fan, Xiao Jiang Hao, Joachim Stöckigt, Yu Zhao. Design, synthesis, and SAR analysis of cytotoxic sinapyl alcohol derivatives. Bioorganic & medicinal chemistry. 2006 Mar; 14(6):2060-71. doi: 10.1016/j.bmc.2005.10.056. [PMID: 16303311]
  • Richard Sibout, Aymerick Eudes, Gregory Mouille, Brigitte Pollet, Catherine Lapierre, Lise Jouanin, Armand Séguin. CINNAMYL ALCOHOL DEHYDROGENASE-C and -D are the primary genes involved in lignin biosynthesis in the floral stem of Arabidopsis. The Plant cell. 2005 Jul; 17(7):2059-76. doi: 10.1105/tpc.105.030767. [PMID: 15937231]
  • Jongwon Choi, Kyoung-Min Shin, Hee-Juhn Park, Hyun-Ju Jung, Hyoung Ja Kim, Yong Sup Lee, Jae-Hwan Rew, Kyung-Tae Lee. Anti-inflammatory and antinociceptive effects of sinapyl alcohol and its glucoside syringin. Planta medica. 2004 Nov; 70(11):1027-32. doi: 10.1055/s-2004-832642. [PMID: 15549657]
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