5-Methoxyindoleacetate (BioDeep_00000001266)

 

Secondary id: BioDeep_00001868405

human metabolite PANOMIX_OTCML-2023 Endogenous natural product


代谢物信息卡片


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

化学式: C11H11NO3 (205.0738896)
中文名称: 5-甲氧基吲哚-3-乙酸
谱图信息: 最多检出来源 Homo sapiens(feces) 13.43%

Reviewed

Last reviewed on 2024-11-11.

Cite this Page

5-Methoxyindoleacetate. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/5-methoxyindoleacetate (retrieved 2024-12-04) (BioDeep RN: BioDeep_00000001266). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: COC1=CC2=C(C=C1)NC=C2CC(=O)O
InChI: InChI=1S/C11H11NO3/c1-15-8-2-3-10-9(5-8)7(6-12-10)4-11(13)14/h2-3,5-6,12H,4H2,1H3,(H,13,14)

描述信息

5-Methoxyindoleacetate, also known as 5-methoxy-IAA or 5-MIAA, 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-Methoxyindoleacetic acid is formed through oxidative deamination. It is identified in the urine, and the concentration is determined to be 1.3 µg/mL using GC-MS (PMID: 12908946). An increase in urinary 5-MIAA excretion was shown in patients with cancer of the stomach, rectum, and lung (PMID: 2446428).
D006133 - Growth Substances > D010937 - Plant Growth Regulators > D007210 - Indoleacetic Acids
5-methoxyindoleacetic acid(5-MIAA) is formed through oxidative deamination.
COVID info from PDB, Protein Data Bank
KEIO_ID M078; [MS2] KO009067
KEIO_ID M078
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS
5-Methoxyindole-3-acetic acid is a metabolite of Melatonin[1].

同义名列表

26 个代谢物同义名

2-(5-Methoxy-1H-indol-3-yl)ethanoic acid; 2-(5-Methoxy-1H-indol-3-yl)acetic acid; 2-(5-Methoxy-1H-indol-3-yl)ethanoate; (5-Methoxy-1H-indol-3-yl)acetic acid; 2-(5-Methoxyindole-3-yl)acetic acid; 2-(5-Methoxy-3-indolyl)acetic acid; 5-Methoxy-1H-indole-3-acetic acid; 2-(5-Methoxyindole-3-yl)acetate; 5-Methyloxyindole-3-acetic acid; 5-Methoxy-3-indolylacetic acid; 5-Methoxyindol-3-ylacetic acid; 5-Methoxyindole-3-acetic acid; 5-Methoxy-3-indoleacetic acid; 5-Methoxyindol-3-ylacetate; 5-Methoxyindoleacetic acid; 5-Methoxyindole-3-acetate; 5-Methoxy-3-indoleacetate; Methoxy indoleacetic acid; Methoxyindoleacetic acid; 5-Methoxy-3-indoleaceate; 5-Methoxyindoleacetate; Methoxyindoleacetate; 5-Methoxy-IAA; 5-MIAA; 5-Methoxyindoleacetate; 5-Methoxyindole-3-acetic acid



数据库引用编号

31 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(3)

PlantCyc(0)

代谢反应

11 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(5)

WikiPathways(0)

Plant Reactome(0)

INOH(1)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(5)

PharmGKB(0)

10 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。



文献列表

  • Taiichi Hikichi, Naohiro Tateda, Toshiaki Miura. Alteration of melatonin secretion in patients with type 2 diabetes and proliferative diabetic retinopathy. Clinical ophthalmology (Auckland, N.Z.). 2011; 5(?):655-60. doi: 10.2147/opth.s19559. [PMID: 21629571]
  • Milan Soskić, Volker Magnus. Binding of ring-substituted indole-3-acetic acids to human serum albumin. Bioorganic & medicinal chemistry. 2007 Jul; 15(13):4595-600. doi: 10.1016/j.bmc.2007.04.005. [PMID: 17481907]
  • Ewa Pobozy, Aleksander Michalski, Joanna Sotowska-Brochocka, Marek Trojanowicz. Determination of melatonin and its precursors and metabolites using capillary electrophoresis with UV and fluorometric detection. Journal of separation science. 2005 Nov; 28(16):2165-72. doi: 10.1002/jssc.200500095. [PMID: 16318213]
  • John M Wilson, Frank McGeorge, Susan Smolinske, Robert Meatherall. A foxy intoxication. Forensic science international. 2005 Feb; 148(1):31-6. doi: 10.1016/j.forsciint.2004.04.017. [PMID: 15607587]
  • Do Yu Soung, Hye Rhi Choi, Ji Young Kim, Jae Kyung No, Jee Hyun Lee, Min Sun Kim, Sook Hee Rhee, Jin Seng Park, Myung Jung Kim, Ryung Yang, Hae Young Chung. Peroxynitrite scavenging activity of indole derivatives: interaction of indoles with peroxynitrite. Journal of medicinal food. 2004; 7(1):84-9. doi: 10.1089/109662004322984752. [PMID: 15117558]
  • Robert Meatherall, Pankaj Sharma. Foxy, a designer tryptamine hallucinogen. Journal of analytical toxicology. 2003 Jul; 27(5):313-7. doi: 10.1093/jat/27.5.313. [PMID: 12908946]
  • Sharon Rossiter, Lisa K Folkes, Peter Wardman. Halogenated indole-3-acetic acids as oxidatively activated prodrugs with potential for targeted cancer therapy. Bioorganic & medicinal chemistry letters. 2002 Sep; 12(18):2523-6. doi: 10.1016/s0960-894x(02)00505-x. [PMID: 12182852]
  • H X Wang, F Liu, T B Ng. Examination of pineal indoles and 6-methoxy-2-benzoxazolinone for antioxidant and antimicrobial effects. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2001 Nov; 130(3):379-88. doi: 10.1016/s1532-0456(01)00264-2. [PMID: 11701394]
  • S Ho, S F Pang, C W Tsang, P L Tang. Effect of light on 5-methoxyindole-3-acetic acid in the rat. Journal of neural transmission (Vienna, Austria : 1996). 2001; 108(5):503-11. doi: 10.1007/s007020170052. [PMID: 11459072]
  • H Kusuhara, T Sekine, N Utsunomiya-Tate, M Tsuda, R Kojima, S H Cha, Y Sugiyama, Y Kanai, H Endou. Molecular cloning and characterization of a new multispecific organic anion transporter from rat brain. The Journal of biological chemistry. 1999 May; 274(19):13675-80. doi: 10.1074/jbc.274.19.13675. [PMID: 10224140]
  • P Li, K L Wong, M C Kwan, C W Tsang, S F Pang. Evaluation of fluorinated indole derivatives for electron-capture negative ionization mass spectrometry: application to the measurement of endogenous 5-methoxyindole-3-acetic acid in rat. Journal of mass spectrometry : JMS. 1996 Nov; 31(11):1228-36. doi: 10.1002/(sici)1096-9888(199611)31:11<1228::aid-jms411>3.0.co;2-1. [PMID: 8946731]
  • C W Tsang, O K Leung, P P Lee, S F Pang. Mass spectrometric identification and quantification of endogenous 5-methoxyindole-3-acetic acid in quail tissues. Biochemical and biophysical research communications. 1995 Apr; 209(3):1132-9. doi: 10.1006/bbrc.1995.1615. [PMID: 7537498]
  • F Raynaud, P Pévet. Determination of 5-methoxyindoles in pineal gland and plasma samples by high-performance liquid chromatography with electrochemical detection. Journal of chromatography. 1991 Mar; 564(1):103-13. doi: 10.1016/0378-4347(91)80073-l. [PMID: 1713596]
  • T Ocal-Irez, G Durmus, Y Sekerkiran, C Peker, G Uygur. Effect of a pineal indolamine, 5-methoxyindole-3-acetic acid, on the estrous cycle and reproductive organs of female Wistar albino rats. Brain research. 1989 Jul; 493(1):1-7. doi: 10.1016/0006-8993(89)90993-1. [PMID: 2476196]
  • D J Morton. Effect of methoxyindole administration on plasma cation levels in the rat. Journal of pineal research. 1989; 6(2):141-7. doi: 10.1111/j.1600-079x.1989.tb00411.x. [PMID: 2464684]
  • A A Levchuk, N P Pal'mina, M O Raushenbakh. [Effect of the carcinogenic metabolites of aromatic amino acids on oxidative processes in lipids in vitro and in vivo]. Biulleten' eksperimental'noi biologii i meditsiny. 1987 Jul; 104(7):77-9. doi: ". [PMID: 2441774]
  • T I Sergeeva, T I Raushenbakh, M O Shevchenko, V G Rybal'chenko. [Excretion of 5-hydroxyindole-3-acetic and 5-methoxyindole-3-acetic acids in cancer patients]. Voprosy onkologii. 1987; 33(10):20-5. doi: . [PMID: 2446428]
  • S Higa, S P Markey. Identification and quantification of 5-methoxyindole-3-acetic acid in human urine. Analytical biochemistry. 1985 Jan; 144(1):86-93. doi: 10.1016/0003-2697(85)90087-9. [PMID: 2580458]
  • R M Leone, R E Silman. An investigation of demethylation in the metabolism of methoxytryptamine and methoxytryptophol. Journal of pineal research. 1985; 2(1):87-94. doi: 10.1111/j.1600-079x.1985.tb00630.x. [PMID: 2420959]
  • J A Hoskins, R J Pollitt. The determination of 5-methoxyindole-3-acetic acid in human urine by mass fragmentography. Journal of chromatography. 1978 Mar; 145(2):285-9. doi: 10.1016/s0378-4347(00)81349-3. [PMID: 274448]