5-Hydroxyindoleacetic acid (BioDeep_00000001263)

 

Secondary id: BioDeep_00000397977, BioDeep_00000400111, BioDeep_00000405361

natural product human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite BioNovoGene_Lab2019


代谢物信息卡片


2-(5-hydroxy-1H-indol-3-yl)acetic acid

化学式: C10H9NO3 (191.0582)
中文名称: 5-羟吲哚乙酸, (5-羟基-1H-吲哚-3-基)乙酸, 5-羟基吲哚-3-乙酸, 5-羟吲哚乙酸(5-HIAA)
谱图信息: 最多检出来源 Homo sapiens(feces) 25.24%

Reviewed

Last reviewed on 2024-07-17.

Cite this Page

5-Hydroxyindoleacetic acid. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/5-hydroxyindoleacetic_acid (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000001263). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: c1(ccc2c(c1)c(c[nH]2)CC(=O)O)O
InChI: InChI=1S/C10H9NO3/c12-7-1-2-9-8(4-7)6(5-11-9)3-10(13)14/h1-2,4-5,11-12H,3H2,(H,13,14)

描述信息

5-Hydroxyindoleacetic acid, also known as 5-hydroxyindole-3-acetate or 5-HIAA, belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. 5-Hydroxyindoleacetic acid exists in all living organisms, ranging from bacteria to humans. In humans, 5-hydroxyindoleacetic acid is a breakdown product of serotonin that is excreted in the urine and it also participates in a number of enzymatic reactions. 5-hydroxyindoleacetic acid can be biosynthesized from 5-hydroxyindoleacetaldehyde; which is catalyzed by the mitochondrial enzyme aldehyde dehydrogenase. In addition, 5-hydroxyindoleacetic acid and S-adenosylmethionine can be converted into 5-methoxyindoleacetate and S-adenosylhomocysteine through its interaction with the enzyme acetylserotonin O-methyltransferase. 5-Hydroxyindoleacetic acid is also involved in the metabolism of tryptophan. 5-Hydroxyindoleacetic acid has been found to be associated with several human diseases such as brunner syndrome, friedreichs ataxia, schizophrenia, and olivopontocerebral atrophy; 5-hydroxyindoleacetic acid has also been linked to the inborn metabolic disorder sepiapterin reductase deficiency. Elevated levels of 5-hydroxyindoleacetic acid in urine (>20 uM) are indicative of appendicitis and gastroenteritis (PMID: 11462886). Serotonin and 5-Hydroxyindoleacetic acid are produced in excess amounts by carcinoid tumors, and levels of these substances may be measured in the urine to test for carcinoid tumors (NCI). 5-Hydroxyindoleacetic acid has also been found to be a product of human gut microbiota.
5-Hydroxyindoleacetic acid (5-HIAA) is the main metabolite of serotonin in the human body. In chemical analysis of urine samples, 5-HIAA is used to determine the bodys levels of serotonin. 5-Hydroxyindole-3-acetic acid is found in many foods, some of which are pitanga, dandelion, coconut, and white cabbage.
5-Hydroxyindole-3-acetic acid is the main metabolite of serotonin or metanephrines, which can be used as a biomarker of neuroendocrine tumors.

同义名列表

32 个代谢物同义名

2-(5-hydroxy-1H-indol-3-yl)acetic acid; 5-Hydroxy-1H-indole-3-acetic acid; Acid, 5-hydroxyindolamine acetic; Acetic acid, 5-hydroxyindolamine; 5 Hydroxyindolamine acetic acid; 5-Hydroxyindolamine acetic acid; 5-Hydroxy-indole-3-acetic acid; 5-Hydroxyindol-3-ylacetic acid; Acid, 5-hydroxy-3-indoleacetic; 5-Hydroxy-3-indoleacetic acid; 5 Hydroxy 3 indoleacetic acid; 5-Hydroxy-1H-indole-3-acetate; 5-Hydroxyindole-3-acetic acid; 5-Hydroxy-3-indoleaceacetate; 5-Hydroxy-indole-3-acetate; 5-Hydroxyindoleacetic acid; 5-Hydroxy-3-indolylacetate; 5-Hydroxyindol-3-ylacetate; Acid, hydroxyindoleacetic; 5-Hydroxyindole-3-acetate; Hydroxyindoleacetic acid; 5-Hydroxyindole acetate; 5-Oxyindoleacetic acid; 5-Hydroxyindoleacetate; 5-Hydroxyheteroauxin; Hydroxyindoleacetate; 5-Oxyindoleacetate; 5-Hydroxy-iaa; 5-HIAA; 5HIAA; 5-Hydroxyindole-3-acetic Acid; Heptadecacyclo[54.16.0.02,19.03,16.06,15.07,12.020,37.021,34.024,33.025,30.038,55.039,52.042,51.043,48.057,70.060,69.061,66]doheptaconta-1(56),2(19),3(16),4,6(15),7,9,11,13,17,20(37),21(34),22,24(33),25,27,29,31,35,38(55),39(52),40,42(51),43,45,47,49,53,57(70),58,60(69),61,63,65,67,71-hexatriacontaene



数据库引用编号

44 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(5)

BioCyc(0)

PlantCyc(0)

代谢反应

94 个相关的代谢反应过程信息。

Reactome(85)

BioCyc(0)

WikiPathways(3)

Plant Reactome(0)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(5)

PharmGKB(0)

41 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 4 BDNF, ENO2, POMC, PRL
Endosome membrane 1 SLC6A4
Mitochondrion membrane 1 MAOA
Nucleus 1 PRL
cytosol 5 ENO2, MAOA, SST, TDO2, TPH2
dendrite 3 BDNF, HTR1A, HTR1B
nucleoplasm 2 ATP2B1, PRL
RNA polymerase II transcription regulator complex 1 PRL
Cell membrane 6 ATP2B1, ENO2, HTR1A, HTR1B, HTR3A, SLC6A4
Cytoplasmic side 1 MAOA
Cleavage furrow 1 HTR3A
Multi-pass membrane protein 5 ATP2B1, HTR1A, HTR1B, HTR3A, SLC6A4
Synapse 6 ATP2B1, CRH, HTR1A, HTR3A, SLC6A4, TAC1
glutamatergic synapse 1 ATP2B1
Golgi apparatus 1 NPY
Golgi membrane 1 INS
neuronal cell body 2 SST, TAC1
postsynapse 1 HTR3A
presynaptic membrane 3 ATP2B1, HTR1B, SLC6A4
synaptic vesicle 1 BDNF
Cytoplasmic vesicle, secretory vesicle 1 CHGA
Presynapse 1 SLC6A4
plasma membrane 7 ATP2B1, ENO2, HTR1A, HTR1B, HTR3A, IFNLR1, SLC6A4
synaptic vesicle membrane 1 ATP2B1
Membrane 7 ATP2B1, BDNF, ENO2, HTR3A, IFNLR1, MAOA, SLC6A4
axon 2 BDNF, TAC1
basolateral plasma membrane 1 ATP2B1
extracellular exosome 2 ATP2B1, ENO2
endoplasmic reticulum 1 HTR1B
extracellular space 11 BDNF, CHGA, CRH, ENO2, IL6, INS, NPY, POMC, PRL, SST, TAC1
perinuclear region of cytoplasm 2 BDNF, CHGA
mitochondrion 1 MAOA
intracellular membrane-bounded organelle 1 ATP2B1
Single-pass type I membrane protein 1 IFNLR1
Secreted 9 BDNF, CHGA, CRH, IL6, INS, NPY, POMC, PRL, SST
extracellular region 10 BDNF, CHGA, CRH, IL6, INS, NPY, POMC, PRL, SST, TAC1
Mitochondrion outer membrane 1 MAOA
Single-pass membrane protein 1 MAOA
mitochondrial outer membrane 1 MAOA
photoreceptor inner segment 1 ENO2
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
varicosity 1 CRH
neuronal dense core vesicle lumen 1 CRH
perikaryon 2 CRH, ENO2
postsynaptic membrane 2 HTR3A, SLC6A4
Membrane raft 1 SLC6A4
Cell junction, focal adhesion 1 SLC6A4
focal adhesion 1 SLC6A4
GABA-ergic synapse 2 NPY, SST
secretory granule 2 CHGA, POMC
lateral plasma membrane 1 ATP2B1
Postsynaptic cell membrane 1 HTR3A
Cell projection, neuron projection 1 SLC6A4
neuron projection 3 HTR3A, SLC6A4, TPH2
chromatin 1 PRL
cell projection 1 ATP2B1
serotonin-activated cation-selective channel complex 1 HTR3A
transmembrane transporter complex 1 HTR3A
Basolateral cell membrane 1 ATP2B1
Endomembrane system 1 SLC6A4
endosome lumen 2 INS, PRL
Cell projection, dendrite 1 HTR1A
Presynaptic cell membrane 1 ATP2B1
secretory granule lumen 2 INS, POMC
Golgi lumen 1 INS
endoplasmic reticulum lumen 3 BDNF, IL6, INS
transport vesicle 2 CHGA, INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
immunological synapse 1 ATP2B1
neuronal dense core vesicle 3 CHGA, NPY, SST
Single-pass type IV membrane protein 1 MAOA
calyx of Held 1 HTR1B
Cytoplasmic vesicle, secretory vesicle, neuronal dense core vesicle 2 CHGA, NPY
interleukin-6 receptor complex 1 IL6
phosphopyruvate hydratase complex 1 ENO2
chromaffin granule 1 CHGA
[Serpinin]: Secreted 1 CHGA
photoreceptor ribbon synapse 1 ATP2B1
[Neurotrophic factor BDNF precursor form]: Secreted 1 BDNF
G protein-coupled serotonin receptor complex 1 HTR1B
serotonergic synapse 2 HTR1B, SLC6A4
interleukin-28 receptor complex 1 IFNLR1


文献列表

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