2-Phenylacetamide (BioDeep_00000003076)

 

Secondary id: BioDeep_00000405674

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


(alpha-)2-Phenylacetamide

化学式: C8H9NO (135.0684)
中文名称: 2-苯基乙酰胺
谱图信息: 最多检出来源 Homo sapiens(otcml) 14.34%

分子结构信息

SMILES: C1=CC=C(C=C1)CC(=O)N
InChI: InChI=1S/C8H9NO/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H2,9,10)

描述信息

2-Phenylacetamide is an intermediate in phenylalanine metabolism and styrene degradation(KEGG ID C02505). It is the third to last step in the synthesis of phenylacetylglutamine and is converted from phenylalanine via the enzyme phenylalanine 2-monooxygenase [EC:1.13.12.9]. It is then converted to phenylacetate via the enzyme amidase [EC:3.5.1.4]. [HMDB]
2-Phenylacetamide is an intermediate in phenylalanine metabolism and styrene degradation(KEGG ID C02505). It is the third to last step in the synthesis of phenylacetylglutamine and is converted from phenylalanine via the enzyme phenylalanine 2-monooxygenase [EC:1.13.12.9]. It is then converted to phenylacetate via the enzyme amidase [EC:3.5.1.4].
2-Phenylacetamide is an endogenous metabolite.

同义名列表

20 个代谢物同义名

(alpha-)2-Phenylacetamide; Phenylacetic acid amide; Phenyl-beta-acetylamine; beta-Phenyl-acetylamine; alpha-Toluimidic acid; alpha-Phenylacetamide; Phenyl-b-acetylamine; Phenyl-β-acetylamine; Phenylacetate amide; 2-Phenyl-acetamide; Α-phenylacetamide; 2-PHENYLACETAMIDE; a-Phenylacetamide; Benzeneacetamide; Phenylacetamide; alpha-Toluamide; Α-toluamide; a-Toluamide; 2-Phenylacetamide; 2-Phenylacetamide



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

1 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(1)

  • Phenylalanine Metabolism: Ammonia + Cytochrome c-552 + Phenylpyruvic acid ⟶ Cytochrome c-552 + D-phenylalanine + Water

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。

亚细胞结构定位 关联基因列表
Cytoplasm 7 FST, GPER1, PIK3CG, RAC1, RPS6, SIRT2, SMAD3
Endoplasmic reticulum membrane 3 GPER1, RAC1, RAC2
Mitochondrion membrane 1 GPER1
Nucleus 6 FST, GPER1, RAC1, RPS6, SIRT2, SMAD3
cytosol 8 DUOX2, GPER1, PIK3CG, RAC1, RAC2, RPS6, SIRT2, SMAD3
dendrite 4 GPER1, OPRM1, RAC1, RPS6
mitochondrial membrane 1 GPER1
trans-Golgi network 2 GPER1, RAC1
centrosome 1 SIRT2
nucleoplasm 5 GPER1, RPS6, SCN5A, SCNN1G, SMAD3
Cell membrane 9 FFAR2, FFAR3, KIR3DL1, NOX1, OPRD1, OPRM1, PIK3CG, RAC1, SCN5A
Lipid-anchor 1 RAC1
Cytoplasmic side 1 RAC1
lamellipodium 2 RAC1, RAC2
ruffle membrane 1 RAC1
Cell projection, axon 2 GPER1, OPRM1
Cell projection, growth cone 1 SIRT2
Multi-pass membrane protein 10 DUOX2, FFAR2, FFAR3, GPER1, NOX1, OPRD1, OPRM1, SCN5A, SCNN1G, TMEM97
Golgi apparatus membrane 1 GPER1
Synapse 2 OPRM1, RAC1
cell cortex 1 RAC1
cell junction 2 DUOX2, SCN5A
cell surface 2 DUOX2, SCN5A
dendritic shaft 1 GPER1
glutamatergic synapse 1 RAC1
Golgi apparatus 2 GPER1, OPRM1
Golgi membrane 2 GPER1, INS
growth cone 1 SIRT2
lysosomal membrane 1 GAA
postsynapse 1 RAC1
presynaptic membrane 2 GPER1, OPRD1
sarcolemma 1 SCN5A
Lysosome 2 GAA, TMEM97
endosome 1 OPRM1
plasma membrane 17 DUOX2, FFAR2, FFAR3, GAA, GPER1, KIR3DL1, NOX1, OPRD1, OPRM1, PIK3CG, RAC1, RAC2, SCN5A, SCNN1G, SIRT2, SMAD3, TMEM97
presynaptic active zone 1 GPER1
synaptic vesicle membrane 1 OPRD1
Membrane 13 DUOX2, FFAR2, GAA, GPER1, KIR3DL1, NOX1, OPRD1, OPRM1, PIK3CG, RAC1, RPS6, SCN5A, TMEM97
apical plasma membrane 2 DUOX2, SCNN1G
axon 2 GPER1, OPRM1
caveola 1 SCN5A
extracellular exosome 5 DUOX2, GAA, RAC1, RAC2, SCNN1G
Lysosome membrane 1 GAA
endoplasmic reticulum 6 DUOX2, GPER1, OPRM1, RPS6, SCN5A, TMEM97
extracellular space 2 FST, INS
lysosomal lumen 1 GAA
perinuclear region of cytoplasm 4 GPER1, RPS6, SCN5A, SIRT2
intercalated disc 1 SCN5A
mitochondrion 1 SIRT2
intracellular membrane-bounded organelle 2 GAA, GPER1
postsynaptic density 1 GPER1
chromatin silencing complex 1 SIRT2
Single-pass type I membrane protein 1 KIR3DL1
Secreted 3 GAA, INS, RAC1
extracellular region 4 FST, GAA, INS, RAC1
mitochondrial outer membrane 1 RAC2
hippocampal mossy fiber to CA3 synapse 1 GPER1
anchoring junction 2 DUOX2, NOX1
transcription regulator complex 1 SMAD3
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 SIRT2
Nucleus membrane 1 TMEM97
nuclear membrane 1 TMEM97
external side of plasma membrane 1 SCNN1G
dendritic spine 1 RAC1
T-tubule 1 SCN5A
perikaryon 2 OPRM1, SIRT2
Z disc 1 SCN5A
cytoplasmic vesicle 1 RAC1
nucleolus 4 GPER1, RPS6, SCN5A, SIRT2
midbody 1 SIRT2
Early endosome 2 GPER1, NOX1
apical part of cell 1 DUOX2
recycling endosome 1 GPER1
Apical cell membrane 2 DUOX2, SCNN1G
Cell projection, lamellipodium 1 RAC1
Cytoplasm, perinuclear region 2 SCN5A, SIRT2
heterochromatin 1 SIRT2
Cytoplasm, cytoskeleton 1 SIRT2
Cytoplasm, cytoskeleton, spindle 1 SIRT2
focal adhesion 2 RAC1, RAC2
microtubule 1 SIRT2
spindle 1 SIRT2
lateral plasma membrane 1 SCN5A
nuclear inner membrane 1 SMAD3
receptor complex 1 SMAD3
neuron projection 2 OPRD1, OPRM1
chromatin 1 SMAD3
cell leading edge 1 DUOX2
cell projection 3 FFAR2, NOX1, SIRT2
phagocytic vesicle membrane 1 RAC2
mitotic spindle 1 SIRT2
Chromosome 1 SIRT2
cytoskeleton 1 RAC1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome, centriole 1 SIRT2
centriole 1 SIRT2
cytoplasmic ribonucleoprotein granule 2 RAC1, RPS6
[Isoform 5]: Cytoplasm 1 SIRT2
Nucleus, nucleolus 1 RPS6
chromosome, telomeric region 1 SIRT2
nuclear envelope 2 GPER1, RAC2
Recycling endosome membrane 1 RAC1
Endomembrane system 1 TMEM97
endosome lumen 1 INS
Cytoplasmic vesicle membrane 1 GPER1
sodium channel complex 1 SCNN1G
Cell projection, dendrite 3 GPER1, OPRM1, RAC1
tertiary granule membrane 1 GAA
Melanosome 1 RAC1
cell body 1 RPS6
myelin sheath 1 SIRT2
[Isoform 1]: Cytoplasm 1 SIRT2
Cell membrane, sarcolemma, T-tubule 1 SCN5A
secretory granule lumen 1 INS
secretory granule membrane 1 RAC1
Golgi lumen 1 INS
endoplasmic reticulum lumen 1 INS
axon terminus 2 GPER1, OPRD1
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CG
transport vesicle 1 INS
azurophil granule membrane 1 GAA
rough endoplasmic reticulum membrane 1 TMEM97
paranode region of axon 1 SIRT2
Schmidt-Lanterman incisure 1 SIRT2
small-subunit processome 1 RPS6
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
postsynaptic density membrane 1 OPRD1
neuronal dense core vesicle 1 OPRD1
[Isoform 2]: Cytoplasm 1 SIRT2
meiotic spindle 1 SIRT2
ribonucleoprotein complex 1 RPS6
paranodal junction 1 SIRT2
heteromeric SMAD protein complex 1 SMAD3
SMAD protein complex 1 SMAD3
ficolin-1-rich granule membrane 2 GAA, RAC1
dendrite membrane 1 OPRD1
Rough endoplasmic reticulum 1 TMEM97
keratin filament 1 GPER1
cytosolic ribosome 1 RPS6
voltage-gated sodium channel complex 1 SCN5A
dendritic spine head 1 GPER1
Cell projection, dendritic spine membrane 1 GPER1
dendritic spine membrane 1 GPER1
glial cell projection 1 SIRT2
ribosome 1 RPS6
NADPH oxidase complex 4 DUOX2, NOX1, RAC1, RAC2
Cell projection, invadopodium membrane 1 NOX1
cytosolic small ribosomal subunit 1 RPS6
autolysosome lumen 1 GAA
juxtaparanode region of axon 1 SIRT2
[Isoform 12]: Cytoplasm 1 OPRM1
spine apparatus 1 OPRD1
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CG
Myelin membrane 1 SIRT2
small ribosomal subunit 1 RPS6
lateral loop 1 SIRT2


文献列表

  • Mengnan Zeng, Meng Li, Miao Li, Beibei Zhang, Benke Li, Li Zhang, Weisheng Feng, Xiaoke Zheng. 2-Phenylacetamide Isolated from the Seeds of Lepidium apetalum and Its Estrogen-Like Effects In Vitro and In Vivo. Molecules (Basel, Switzerland). 2018 Sep; 23(9):. doi: 10.3390/molecules23092293. [PMID: 30205508]
  • Luc H Boudreau, Jacques Maillet, Luc M LeBlanc, Jacques Jean-François, Mohamed Touaibia, Nicolas Flamand, Marc E Surette. Caffeic acid phenethyl ester and its amide analogue are potent inhibitors of leukotriene biosynthesis in human polymorphonuclear leukocytes. PloS one. 2012; 7(2):e31833. doi: 10.1371/journal.pone.0031833. [PMID: 22347509]
  • Vikas Sharma, Jente Boonen, Nagendra S Chauhan, Mayank Thakur, Bart De Spiegeleer, V K Dixit. Spilanthes acmella ethanolic flower extract: LC-MS alkylamide profiling and its effects on sexual behavior in male rats. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2011 Oct; 18(13):1161-9. doi: 10.1016/j.phymed.2011.06.001. [PMID: 21757328]
  • G Kanagasabapathy, S N A Malek, U R Kuppusamy, S Vikineswary. Chemical composition and antioxidant properties of extracts of fresh fruiting bodies of Pleurotus sajor-caju (Fr.) Singer. Journal of agricultural and food chemistry. 2011 Mar; 59(6):2618-26. doi: 10.1021/jf104133g. [PMID: 21348494]
  • J Boonen, B Baert, C Burvenich, P Blondeel, S De Saeger, B De Spiegeleer. LC-MS profiling of N-alkylamides in Spilanthes acmella extract and the transmucosal behaviour of its main bio-active spilanthol. Journal of pharmaceutical and biomedical analysis. 2010 Nov; 53(3):243-9. doi: 10.1016/j.jpba.2010.02.010. [PMID: 20227845]
  • Akihiro Furukawa, Tsuyoshi Arita, Susumu Satoh, Kenji Wakabayashi, Shinko Hayashi, Yumi Matsui, Kazushi Araki, Masanori Kuroha, Jun Ohsumi. Discovery of a novel selective PPARgamma modulator from (-)-Cercosporamide derivatives. Bioorganic & medicinal chemistry letters. 2010 Apr; 20(7):2095-8. doi: 10.1016/j.bmcl.2010.02.073. [PMID: 20219371]
  • Rory P Remmel, Brenda C Crews, Kevin R Kozak, Amit S Kalgutkar, Lawrence J Marnett, Amit S Algutkar. Studies on the metabolism of the novel, selective cyclooxygenase-2 inhibitor indomethacin phenethylamide in rat, mouse, and human liver microsomes: identification of active metabolites. Drug metabolism and disposition: the biological fate of chemicals. 2004 Jan; 32(1):113-22. doi: 10.1124/dmd.32.1.113. [PMID: 14709628]
  • Kazumi Osada, Kunio Yamazaki, Maryanne Curran, Judith Bard, Benjamin P C Smith, Gary K Beauchamp. The scent of age. Proceedings. Biological sciences. 2003 May; 270(1518):929-33. doi: 10.1098/rspb.2002.2308. [PMID: 12803907]