Phenylpyruvate (BioDeep_00000001693)

 

Secondary id: BioDeep_00000405215, BioDeep_00000870067

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019


代谢物信息卡片


2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto)

化学式: C9H8O3 (164.0473)
中文名称: 苯丙酮酸钠, 苯丙酮酸
谱图信息: 最多检出来源 Homo sapiens(blood) 20.51%

Reviewed

Last reviewed on 2024-09-14.

Cite this Page

Phenylpyruvate. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/phenylpyruvate (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000001693). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: C1=CC=C(C=C1)CC(=O)C(=O)O
InChI: InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12)

描述信息

Phenylpyruvic acid is a keto-acid that is an intermediate or catabolic byproduct of phenylalanine metabolism. It has a slight honey-like odor. Levels of phenylpyruvate are normally very low in blood or urine. High levels of phenylpyruvic acid can be found in the urine of individuals with phenylketonuria (PKU), an inborn error of metabolism. PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but to phenylpyruvic acid. In particular, excessive phenylalanine can be metabolized into phenylketones through, a transaminase pathway route involving glutamate. Metabolites of this transamination reaction include phenylacetate, phenylpyruvate and phenethylamine. In persons with PKU, dietary phenylalanine either accumulates in the body or some of it is converted to phenylpyruvic acid. Individuals with PKU tend to excrete large quantities of phenylpyruvate, phenylacetate and phenyllactate, along with phenylalanine, in their urine. If untreated, mental retardation effects and microcephaly are evident by the first year along with other symptoms which include: unusual irritability, epileptic seizures and skin lesions. Hyperactivity, EEG abnormalities and seizures, and severe learning disabilities are major clinical problems later in life. A "musty or mousy" odor of skin, hair, sweat and urine (due to phenylacetate accumulation); and a tendency to hypopigmentation and eczema are also observed. The neural-development effects of PKU are primarily due to the disruption of neurotransmitter synthesis. In particular, phenylalanine is a large, neutral amino acid which moves across the blood-brain barrier (BBB) via the large neutral amino acid transporter (LNAAT). Excessive phenylalanine in the blood saturates the transporter. Thus, excessive levels of phenylalanine significantly decrease the levels of other LNAAs in the brain. But since these amino acids are required for protein and neurotransmitter synthesis, phenylalanine accumulation disrupts brain development, leading to mental retardation. Phenylpyruvic acid is also a microbial metabolite, it can be produced by Lactobacillus plantarum (PMID: 9687465).
Flavouring ingredient
Phenylpyruvic acid is used in the synthesis of 3-phenyllactic acid (PLA) by lactate dehydrogenase[1].
Phenylpyruvic acid is used in the synthesis of 3-phenyllactic acid (PLA) by lactate dehydrogenase[1].

同义名列表

48 个代谢物同义名

2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto); alpha-Oxo-benzenepropanoic acid; alpha-Oxobenzenepropionic acid; α-Ketohydrocinnamic acid; alpha-Oxobenzenepropanoic acid; 2-Oxo-3-phenylpropanoic acid; 3-Phenyl-2-oxopropionic acid; alpha-Ketohydrocinnamic acid; 3-Phenyl-2-oxopropanoic acid; 2-Oxo-3-phenylpropionic acid; alpha-Oxo-benzenepropanoate; a-Oxo-benzenepropanoic acid; α-Oxo-benzenepropanoic acid; α-Ketohydrocinnamate; α-Oxobenzenepropionic acid; α-Oxobenzenepropanoic acid; β-Phenylpyruvic acid; Phenylbrenztraubensaeure; 3-Phenyl-2-oxopropanoate; 2-Oxo-3-phenylpropanoate; alpha-Ketohydrocinnamate; α-Ketohydrocinnamic acid; a-Ketohydrocinnamic acid; a-Oxo-benzenepropanoate; beta-Phenylpyruvic acid; keto-Phenylpyruvic acid; α-Oxo-benzenepropanoate; a-Hydroxycinnamic acid; Phenylpyroracemic acid; β-Phenylpyruvate; Sodium phenylpyruvate; a-Ketohydrocinnamate; α-Ketohydrocinnamate; b-Phenylpyruvic acid; β-Phenylpyruvic acid; 3-Phenylpyruvic acid; beta-Phenylpyruvate; Keto-phenylpyruvate; Phenylpyroracemate; Phenylpyruvic acid; b-Phenylpyruvate; 3-PHENYLPYRUVate; β-Phenylpyruvate; Phenylpyruvate; FEMA 3892; Phenylpyruvic acid; Phenylpyruvic acid; Phenylpyruvate



数据库引用编号

28 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(0)

代谢反应

513 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(6)

WikiPathways(0)

Plant Reactome(484)

INOH(3)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(20)

PharmGKB(0)

6 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 CAT, DAO, G6PD, HPD, KYAT1, MIF, PFDN5, PKM
Peripheral membrane protein 4 DAO, G6PD, HPD, HSD17B6
Endoplasmic reticulum membrane 1 HPD
Nucleus 4 PDC, PFDN5, PKM, PPARA
cytosol 11 CAT, DAO, G6PD, HPD, KYAT1, MIF, PAH, PDC, PFDN5, PKM, TAT
nucleoplasm 2 MIF, PPARA
Cell membrane 1 DAO
Early endosome membrane 1 HSD17B6
Multi-pass membrane protein 1 SLC36A3
Golgi apparatus membrane 1 HPD
cell surface 1 MIF
Golgi membrane 2 HPD, INS
mitochondrial inner membrane 1 LDHD
Cytoplasm, cytosol 4 DAO, G6PD, KYAT1, PDC
Lysosome 1 IL4I1
acrosomal vesicle 1 IL4I1
plasma membrane 4 DAO, GCG, ME3, MIF
presynaptic active zone 1 DAO
Membrane 4 CAT, G6PD, ME3, SLC36A3
extracellular exosome 6 CAT, DAO, G6PD, HPD, MIF, PKM
Lumenal side 1 HSD17B6
endoplasmic reticulum 1 HSD17B6
extracellular space 5 DAO, GCG, IL4, INS, MIF
bicellular tight junction 1 DAO
mitochondrion 5 CAT, KYAT1, LDHD, ME3, PKM
protein-containing complex 1 CAT
intracellular membrane-bounded organelle 3 CAT, G6PD, HSD17B6
Microsome membrane 1 HSD17B6
Secreted 6 DAO, GCG, IL4, IL4I1, INS, MIF
extracellular region 8 CAT, DAO, GCG, IL4, IL4I1, INS, MIF, PKM
cytoplasmic side of plasma membrane 1 G6PD
Single-pass membrane protein 1 ME3
mitochondrial matrix 2 CAT, ME3
Extracellular side 1 DAO
centriolar satellite 1 G6PD
photoreceptor inner segment 1 PDC
photoreceptor outer segment 1 PDC
Extracellular vesicle 1 PKM
vesicle 2 MIF, PKM
focal adhesion 1 CAT
Peroxisome 2 CAT, DAO
Peroxisome matrix 2 CAT, DAO
peroxisomal matrix 2 CAT, DAO
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 1 PKM
cilium 1 PKM
chromatin 1 PPARA
cell projection 1 DAO
Cell projection, cilium, photoreceptor outer segment 1 PDC
Secreted, extracellular space 1 DAO
Cytoplasmic vesicle, secretory vesicle, acrosome 1 IL4I1
sperm midpiece 1 IL4I1
endosome lumen 1 INS
intermediate filament cytoskeleton 1 PFDN5
ficolin-1-rich granule lumen 3 CAT, MIF, PKM
secretory granule lumen 5 CAT, GCG, INS, MIF, PKM
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 GCG, INS
specific granule lumen 1 DAO
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
immunological synapse 1 IL4I1
[Isoform 2]: Nucleus 1 PDC
prefoldin complex 1 PFDN5
Rough endoplasmic reticulum 1 PKM
[Glucagon-like peptide 1]: Secreted 1 GCG
catalase complex 1 CAT
vacuolar membrane 1 SLC36A3
[Isoform M2]: Cytoplasm 1 PKM
[Isoform M1]: Cytoplasm 1 PKM


文献列表

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