4-Hydroxyphenylacetaldehyde (BioDeep_00000005309)

 

Secondary id: BioDeep_00000875067, BioDeep_00001868929

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


2-(4-Hydroxyphenyl)acetaldehyde

化学式: C8H8O2 (136.0524)
中文名称: 4-羟基苯乙醛
谱图信息: 最多检出来源 Homo sapiens(plant) 17.46%

分子结构信息

SMILES: C1=CC(=CC=C1CC=O)O
InChI: InChI=1S/C8H8O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,6,10H,5H2

描述信息

4-Hydroxyphenylacetaldehyde is a byproduct of tyrosine metabolism.
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同义名列表

10 个代谢物同义名

2-(4-Hydroxyphenyl)acetaldehyde; (p-Hydroxyphenyl)acetaldehyde; (4-Hydroxyphenyl)acetaldehyde; 4-Hydroxybenzeneacetaldehyde; 4-Hydroxyphenylacetaldehyde; p-Hydroxyphenylacetaldehyde; 4-Hydroxyphenylacetadehyde; POH-PH-CH2CHO; 4-HPAA; 4-Hydroxyphenylacetaldehyde



数据库引用编号

18 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(5)

BioCyc(2)

PlantCyc(1)

代谢反应

167 个相关的代谢反应过程信息。

Reactome(63)

BioCyc(9)

WikiPathways(0)

Plant Reactome(0)

INOH(2)

PlantCyc(90)

COVID-19 Disease Map(1)

PathBank(2)

  • Tyrosine Metabolism: 4-Hydroxyphenylpyruvic acid + L-Alanine ⟶ L-Tyrosine + Pyruvic acid
  • Tyrosine Metabolism: 4-Fumarylacetoacetic acid + Water ⟶ Acetoacetic acid + Fumaric acid + Hydrogen Ion

PharmGKB(0)

38 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 AOC3, APOE, ARHGAP45, CAT, FHL2, LDHA, NCS1, POMC
Peripheral membrane protein 2 CYP1B1, LPL
Endoplasmic reticulum membrane 3 CYP1B1, HSP90B1, SOAT1
Nucleus 5 APOE, FHL2, HSP90B1, LDHA, MPO
cytosol 7 AKR1A1, ARHGAP45, CAT, HBB, HSP90B1, LDHA, PGK1
dendrite 2 APOE, NCS1
nucleoplasm 2 FHL2, MPO
Cell membrane 3 AOC3, LPL, NCS1
Lipid-anchor 1 NCS1
ruffle membrane 1 ARHGAP45
Multi-pass membrane protein 1 SOAT1
Synapse 1 AKR1A1
cell surface 2 AOC3, LPL
glutamatergic synapse 1 APOE
Golgi apparatus 3 AOC3, APOE, NCS1
neuronal cell body 1 APOE
smooth endoplasmic reticulum 1 HSP90B1
Cytoplasm, cytosol 1 AKR1A1
Lysosome 1 MPO
plasma membrane 7 AOC3, APOE, ARHGAP45, IFNLR1, LPL, MSR1, NCS1
Membrane 13 AOC3, APOE, ARHGAP45, CAT, CYP1B1, HBB, HSP90B1, IFNLR1, LDHA, MSR1, NCS1, PGK1, SOAT1
apical plasma membrane 1 AKR1A1
axon 1 NCS1
extracellular exosome 8 AKR1A1, APOE, CAT, HBB, HSP90B1, LDHA, MPO, PGK1
endoplasmic reticulum 4 AOC3, APOE, HSP90B1, SOAT1
extracellular space 7 AKR1A1, APOE, HBB, LPL, MPO, PGK1, POMC
perinuclear region of cytoplasm 2 HSP90B1, NCS1
mitochondrion 3 CAT, CYP1B1, LDHA
protein-containing complex 2 CAT, HSP90B1
intracellular membrane-bounded organelle 4 CAT, CYP1B1, MPO, NCS1
Microsome membrane 1 CYP1B1
postsynaptic density 1 NCS1
Single-pass type I membrane protein 1 IFNLR1
Secreted 3 APOE, LPL, POMC
extracellular region 8 APOE, ARHGAP45, CAT, HBB, HSP90B1, LPL, MPO, POMC
mitochondrial matrix 1 CAT
Extracellular side 1 LPL
Endosome, multivesicular body 1 APOE
Extracellular vesicle 1 APOE
Secreted, extracellular space, extracellular matrix 2 APOE, LPL
chylomicron 2 APOE, LPL
high-density lipoprotein particle 1 APOE
low-density lipoprotein particle 2 APOE, MSR1
multivesicular body 1 APOE
very-low-density lipoprotein particle 2 APOE, LPL
Z disc 2 FHL2, HRC
midbody 1 HSP90B1
Early endosome 2 AOC3, APOE
Single-pass type II membrane protein 2 AOC3, MSR1
Apical cell membrane 1 AKR1A1
Cell projection, ruffle membrane 1 ARHGAP45
Cytoplasm, perinuclear region 1 NCS1
Membrane raft 1 PGK1
focal adhesion 3 CAT, FHL2, HSP90B1
extracellular matrix 1 APOE
Peroxisome 1 CAT
collagen trimer 1 MSR1
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 2 APOE, HSP90B1
secretory granule 2 MPO, POMC
Secreted, extracellular space 1 APOE
blood microparticle 2 APOE, HBB
microvillus 1 AOC3
Melanosome 2 APOE, HSP90B1
sperm plasma membrane 1 HSP90B1
Cytoplasm, myofibril, sarcomere, Z line 1 FHL2
azurophil granule 1 MPO
ficolin-1-rich granule lumen 2 CAT, HBB
secretory granule lumen 3 ARHGAP45, CAT, POMC
endoplasmic reticulum lumen 3 APOE, HRC, HSP90B1
tertiary granule lumen 1 HBB
endocytic vesicle membrane 1 MSR1
azurophil granule lumen 2 ARHGAP45, MPO
Sarcoplasmic reticulum membrane 1 HRC
clathrin-coated endocytic vesicle membrane 1 APOE
Sarcoplasmic reticulum lumen 2 HRC, HSP90B1
phagocytic vesicle lumen 1 MPO
synaptic cleft 1 APOE
discoidal high-density lipoprotein particle 1 APOE
oxidoreductase complex 1 LDHA
hemoglobin complex 1 HBB
endocytic vesicle lumen 3 APOE, HBB, HSP90B1
haptoglobin-hemoglobin complex 1 HBB
chylomicron remnant 1 APOE
intermediate-density lipoprotein particle 1 APOE
lipoprotein particle 1 APOE
multivesicular body, internal vesicle 1 APOE
catalase complex 1 CAT
catalytic complex 1 LPL
endoplasmic reticulum chaperone complex 1 HSP90B1
interleukin-28 receptor complex 1 IFNLR1


文献列表

  • Xiang Sheng, Fahmi Himo. Enzymatic Pictet-Spengler Reaction: Computational Study of the Mechanism and Enantioselectivity of Norcoclaurine Synthase. Journal of the American Chemical Society. 2019 07; 141(28):11230-11238. doi: 10.1021/jacs.9b04591. [PMID: 31265268]
  • Michael P Torrens-Spence, Glenda Gillaspy, Bingyu Zhao, Kim Harich, Robert H White, Jianyong Li. Biochemical evaluation of a parsley tyrosine decarboxylase results in a novel 4-hydroxyphenylacetaldehyde synthase enzyme. Biochemical and biophysical research communications. 2012 Feb; 418(2):211-6. doi: 10.1016/j.bbrc.2011.12.124. [PMID: 22266321]
  • Isabel Desgagné-Penix, Morgan F Khan, David C Schriemer, Dustin Cram, Jacek Nowak, Peter J Facchini. Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures. BMC plant biology. 2010 Nov; 10(?):252. doi: 10.1186/1471-2229-10-252. [PMID: 21083930]
  • Luis González-Candelas, Santiago Alamar, Paloma Sánchez-Torres, Lorenzo Zacarías, Jose F Marcos. A transcriptomic approach highlights induction of secondary metabolism in citrus fruit in response to Penicillium digitatum infection. BMC plant biology. 2010 Aug; 10(?):194. doi: 10.1186/1471-2229-10-194. [PMID: 20807411]
  • Yuan-Yuan Xie, Dan Yuan, Jing-Yu Yang, Li-Hui Wang, Chun-Fu Wu. Cytotoxic activity of flavonoids from the flowers of Chrysanthemum morifolium on human colon cancer Colon205 cells. Journal of Asian natural products research. 2009 Sep; 11(9):771-8. doi: 10.1080/10286020903128470. [PMID: 20183323]
  • Christian Radauer, Peter Lackner, Heimo Breiteneder. The Bet v 1 fold: an ancient, versatile scaffold for binding of large, hydrophobic ligands. BMC evolutionary biology. 2008 Oct; 8(?):286. doi: 10.1186/1471-2148-8-286. [PMID: 18922149]
  • Anna Mura, Francesca Pintus, Antonella Fais, Simona Porcu, Marcella Corda, Delia Spanò, Rosaria Medda, Giovanni Floris. Tyramine oxidation by copper/TPQ amine oxidase and peroxidase from Euphorbia characias latex. Archives of biochemistry and biophysics. 2008 Jul; 475(1):18-24. doi: 10.1016/j.abb.2008.03.034. [PMID: 18423366]
  • Alessandra Pasquo, Alessandra Bonamore, Stefano Franceschini, Alberto Macone, Alberto Boffi, Andrea Ilari. Cloning, expression, crystallization and preliminary X-ray data analysis of norcoclaurine synthase from Thalictrum flavum. Acta crystallographica. Section F, Structural biology and crystallization communications. 2008 Apr; 64(Pt 4):281-3. doi: 10.1107/s1744309108005678. [PMID: 18391427]
  • Katherine G Zulak, Aalim M Weljie, Hans J Vogel, Peter J Facchini. Quantitative 1H NMR metabolomics reveals extensive metabolic reprogramming of primary and secondary metabolism in elicitor-treated opium poppy cell cultures. BMC plant biology. 2008 Jan; 8(?):5. doi: 10.1186/1471-2229-8-5. [PMID: 18211706]
  • Hiromichi Minami, Emilyn Dubouzet, Kinuko Iwasa, Fumihiko Sato. Functional analysis of norcoclaurine synthase in Coptis japonica. The Journal of biological chemistry. 2007 Mar; 282(9):6274-82. doi: 10.1074/jbc.m608933200. [PMID: 17204481]
  • Alessandra Padiglia, Giovanni Floris, Silvia Longu, M Eugenia Schininà, Jens Z Pedersen, Alessandro Finazzi Agrò, Francesco De Angelis, Rosaria Medda. Inhibition of lentil copper/TPQ amine oxidase by the mechanism-based inhibitor derived from tyramine. Biological chemistry. 2004 Mar; 385(3-4):323-9. doi: 10.1515/bc.2004.028. [PMID: 15134347]
  • N Samanani, P J Facchini. Isolation and partial characterization of norcoclaurine synthase, the first committed step in benzylisoquinoline alkaloid biosynthesis, from opium poppy. Planta. 2001 Oct; 213(6):898-906. doi: 10.1007/s004250100581. [PMID: 11722126]
  • M Exner, E Alt, M Hermann, R Hofbauer, S Kapiotis, P Quehenberger, W Speiser, E Minar, B Gmeiner. p-Hydroxyphenylacetaldehyde, the major product of tyrosine oxidation by the activated myeloperoxidase system can act as an antioxidant in LDL. FEBS letters. 2001 Feb; 490(1-2):28-31. doi: 10.1016/s0014-5793(01)02131-7. [PMID: 11172805]
  • S L Hazen, J P Gaut, J R Crowley, F F Hsu, J W Heinecke. Elevated levels of protein-bound p-hydroxyphenylacetaldehyde, an amino-acid-derived aldehyde generated by myeloperoxidase, are present in human fatty streaks, intermediate lesions and advanced atherosclerotic lesions. The Biochemical journal. 2000 Dec; 352 Pt 3(?):693-9. doi: . [PMID: 11104675]
  • J I Heller, J R Crowley, S L Hazen, D M Salvay, P Wagner, S Pennathur, J W Heinecke. p-hydroxyphenylacetaldehyde, an aldehyde generated by myeloperoxidase, modifies phospholipid amino groups of low density lipoprotein in human atherosclerotic intima. The Journal of biological chemistry. 2000 Apr; 275(14):9957-62. doi: 10.1074/jbc.275.14.9957. [PMID: 10744670]
  • S L Hazen, J Heller, F F Hsu, A d'Avignon, J W Heinecke. Synthesis, isolation, and characterization of the adduct formed in the reaction of p-hydroxyphenylacetaldehyde with the amino headgroup of phosphatidylethanolamine and phosphatidylserine. Chemical research in toxicology. 1999 Jan; 12(1):19-27. doi: 10.1021/tx980147s. [PMID: 9894014]
  • S L Hazen, J P Gaut, F F Hsu, J R Crowley, A d'Avignon, J W Heinecke. p-Hydroxyphenylacetaldehyde, the major product of L-tyrosine oxidation by the myeloperoxidase-H2O2-chloride system of phagocytes, covalently modifies epsilon-amino groups of protein lysine residues. The Journal of biological chemistry. 1997 Jul; 272(27):16990-8. doi: 10.1074/jbc.272.27.16990. [PMID: 9202012]
  • S L Hazen, F F Hsu, J W Heinecke. p-Hydroxyphenylacetaldehyde is the major product of L-tyrosine oxidation by activated human phagocytes. A chloride-dependent mechanism for the conversion of free amino acids into reactive aldehydes by myeloperoxidase. The Journal of biological chemistry. 1996 Jan; 271(4):1861-7. doi: 10.1074/jbc.271.4.1861. [PMID: 8567631]
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