L-3-Phenyllactic acid (BioDeep_00000001292)

 

Secondary id: BioDeep_00000229628, BioDeep_00000265221, BioDeep_00000405357, BioDeep_00000406092, BioDeep_00000593349, BioDeep_00001868918, BioDeep_00001871406

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


(2R)-2-hydroxy-3-phenylpropanoic acid

化学式: C9H10O3 (166.062991)
中文名称: L-(-)-3-苯乳酸, L-（-）-3-苯基乳酸, DL-3-苯基-2-羟丙酸, DL-3-苯基乳酸, D-苯基乳酸
谱图信息: 最多检出来源 Homo sapiens(feces) 21.5%

Reviewed

Last reviewed on 2024-07-04.

Cite this Page

L-3-Phenyllactic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/l-3-phenyllactic_acid (retrieved 2024-12-04) (BioDeep RN: BioDeep_00000001292). 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(C(=O)O)O
InChI: InChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)

描述信息

L-3-Phenyllactic acid (or PLA) is a chiral aromatic compound involved in phenylalanine metabolism. It is likely produced from phenylpyruvate via the action of lactate dehydrogenase. The D-form of this organic acid is typically derived from bacterial sources while the L-form is almost certainly endogenous. Levels of phenyllactate are normally very low in blood or urine. High levels of PLA in the urine or blood are often indicative of phenylketonuria (PKU) and hyperphenylalaninemia (HPA). PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but to phenylpyruvic acid (a precursor of phenylactate). In particular, excessive phenylalanine is typically 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 and then to phenyllactate through the action of lactate dehydrogenase. 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. [HMDB]
L-3-Phenyllactic acid (or PLA) is a chiral aromatic compound involved in phenylalanine metabolism. It is likely produced from phenylpyruvate via the action of lactate dehydrogenase. The D-form of this organic acid is typically derived from bacterial sources while the L-form is almost certainly endogenous. Levels of phenyllactate are normally very low in blood or urine. High levels of PLA in the urine or blood are often indicative of phenylketonuria (PKU) and hyperphenylalaninemia (HPA). PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but to phenylpyruvic acid (a precursor of phenylactate). In particular, excessive phenylalanine is typically 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 and then to phenyllactate through the action of lactate dehydrogenase. 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.

(±)-3-Phenyllactic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=828-01-3 (retrieved 2024-07-04) (CAS RN: 828-01-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
(S)-2-Hydroxy-3-phenylpropanoic acid is a product of phenylalanine catabolism. An elevated level of phenyllactic acid is found in body fluids of patients with or phenylketonuria.
D-?(+)?-?Phenyllactic acid is an anti-bacterial agent, excreted by Geotrichum candidum, inhibits a range of Gram-positive from humans and foodstuffs and Gram-negative bacteria found in humans[1].
DL-3-Phenyllactic acid is a broad-spectrum antimicrobial compound.
DL-3-Phenyllactic acid is a broad-spectrum antimicrobial compound.

同义名列表

52 个代谢物同义名

ALPHA-HYDROXY-BETA-phenyl-propionIC ACID; (S)-alpha-Hydroxy-benzenepropanoic acid; (2S)-2-hydroxy-3-phenylpropanoic acid; (2R)-2-hydroxy-3-phenylpropanoic acid; (2S)-2-Hydroxy-3-phenylpropionic acid; (-)-2-Hydroxy-3-phenylpropanoic acid; (-)-2-Hydroxy-3-phenylpropionic acid; (R)-2-Hydroxy-3-phenylpropionic acid; L-2-Hydroxy-3-phenyl-propionic acid; (S)-a-Hydroxy-benzenepropanoic acid; (S)-alpha-Hydroxy-benzenepropanoate; (2S)-2-Hydroxy-3-phenylpropanoate; (2S)-2-Hydroxy-3-phenylpropionate; (-)-2-Hydroxy-3-phenylpropanoate; (-)-2-Hydroxy-3-phenylpropionate; (S)-a-Hydroxy-benzenepropanoate; (-)-beta-Phenyllactic acid; D-(+)-3-Phenyllactic acid; (R)-3-(Phenyl)lactic acid; L-(-)-3-Phenyllactic acid; L-beta-Phenyllactic acid; (S)-3-Phenyl-lactic acid; D-beta-Phenyllactic acid; (-)-b-Phenyllactic acid; (S)-3-Phenyllactic acid; (R)-3-Phenyllactic acid; (-)-3-Phenyllactic acid; (-)-beta-Phenyllactate; DL-3-Phenyllactic acid; (R)-Phenyllactic acid; (R)-3-(Phenyl)lactate; (S)-beta-Phenyllactic; L-3-Phenyllactic acid; D-3-phenyllactic acid; (S)-3-Phenyl-lactate; (R)-3-Phenyllactate; (-)-b-Phenyllactate; (-)-3-Phenyllactate; (S)-b-Phenyllactic; D-3-Phenyllactate; Phenyllactic acid; L-3-Phenyllactate; (R)-Phenyllactate; L-Phenyl lactate; 3-Phenyllactate; Phenyllactate; HFA; DL-3-Phenyllactic acid; (S)-2-Hydroxy-3-phenylpropanoic acid; D-?(+)?-?Phenyllactic acid; Phenyllactate; L-(-)-3-Phenyllactic acid



数据库引用编号

30 个数据库交叉引用编号

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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。



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