6-Hydroxymelatonin (BioDeep_00000017783)

 

Secondary id: BioDeep_00000001273

human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite


代谢物信息卡片


N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide

化学式: C13H16N2O3 (248.1161)
中文名称: 6-羟基褪黑素
谱图信息: 最多检出来源 Homo sapiens(plant) 3.79%

Reviewed

Last reviewed on 2024-11-11.

Cite this Page

6-Hydroxymelatonin. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/6-hydroxymelatonin (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000017783). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC(=O)NCCC1=CNC2=CC(=C(C=C21)OC)O
InChI: InChI=1S/C13H16N2O3/c1-8(16)14-4-3-9-7-15-11-6-12(17)13(18-2)5-10(9)11/h5-7,15,17H,3-4H2,1-2H3,(H,14,16)

描述信息

6-Hydroxymelatonin, also known as lopac-H-0627, belongs to the class of organic compounds known as hydroxyindoles. These are organic compounds containing an indole moiety that carries a hydroxyl group. 6-Hydroxymelatonin is considered to be a practically insoluble (in water) and relatively neutral molecule. 6-Hydroxymelatonin has been found in human liver and kidney tissues, and has also been detected in multiple biofluids, such as urine and blood. Within the cell, 6-hydroxymelatonin is primarily located in the cytoplasm. 6-Hydroxymelatonin is the main primary metabolite that can be biosynthesized from melatonin through its interaction with the enzyme cytochrome P450 (CYP) 1A2 (PMID: 11452239). In humans, 6-hydroxymelatonin is involved in the tryptophan metabolism pathway.
Melatonin is a hormone that is metabolized by cytochrome P450 (CYP) 1A2 to its main primary metabolite 6-hydroxymelatonin. (PMID 11452239) [HMDB]. 6-Hydroxymelatonin is found in many foods, some of which are garden onion, millet, peppermint, and apricot.
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
D020011 - Protective Agents > D002316 - Cardiotonic Agents
D002317 - Cardiovascular Agents
6-Hydroxymelatonin is a primary metabolic of Melatonin, which is metabolized by cytochrome P450 (CYP) 1A2.

同义名列表

6 个代谢物同义名

N-[2-(6-hydroxy-5-methoxy-1H-indol-3-yl)ethyl]acetamide; 6-Hydroxy-N-acetyl-5-methoxytryptamine; 6-HYDROXYMELATONIN; 6-Oxymelatonin; Lopac-H-0627; 6-Hydroxymelatonin



数据库引用编号

16 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

0 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(0)

PharmGKB(0)

1 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 11 AHR, CASP3, CAT, CYP1A1, CYP2C19, CYP2C9, MTOR, PPARG, SULT1A1, SULT1C4, TYR
Peripheral membrane protein 3 CYP1A1, CYP1B1, MTOR
Endoplasmic reticulum membrane 7 CYP1A1, CYP1A2, CYP1B1, CYP2C19, CYP2C9, MTOR, P4HTM
Nucleus 4 AHR, CASP3, MTOR, PPARG
cytosol 7 AHR, CASP3, CAT, MTOR, PPARG, SULT1A1, SULT1C4
dendrite 1 MTOR
phagocytic vesicle 1 MTOR
nucleoplasm 6 AHR, CASP3, CD2, MNT, MTOR, PPARG
RNA polymerase II transcription regulator complex 1 PPARG
Cell membrane 1 CD2
Cytoplasmic side 1 MTOR
Multi-pass membrane protein 1 SLC45A2
Golgi apparatus membrane 1 MTOR
cell surface 1 CD2
glutamatergic synapse 1 CASP3
Golgi apparatus 1 CD2
Golgi membrane 1 MTOR
lysosomal membrane 1 MTOR
mitochondrial inner membrane 1 CYP1A1
neuronal cell body 1 CASP3
Cytoplasm, cytosol 1 SULT1C4
Lysosome 2 MTOR, TYR
plasma membrane 3 CD2, CYP2C19, CYP2C9
Membrane 5 CAT, CYP1B1, MTOR, P4HTM, SLC45A2
extracellular exosome 1 CAT
Lysosome membrane 1 MTOR
endoplasmic reticulum 1 P4HTM
extracellular space 2 CXCL8, GNRH1
perinuclear region of cytoplasm 2 PPARG, TYR
mitochondrion 3 CAT, CYP1A1, CYP1B1
protein-containing complex 3 AHR, CAT, CD2
intracellular membrane-bounded organelle 8 CAT, CYP1A1, CYP1A2, CYP1B1, CYP2C19, CYP2C9, PPARG, TYR
Microsome membrane 5 CYP1A1, CYP1A2, CYP1B1, CYP2C9, MTOR
postsynaptic density 1 CASP3
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 2 CD2, TYR
Secreted 2 CGB5, CXCL8
extracellular region 5 CAT, CD2, CGB5, CXCL8, GNRH1
cytoplasmic side of plasma membrane 1 CD2
Mitochondrion outer membrane 1 MTOR
mitochondrial outer membrane 1 MTOR
mitochondrial matrix 1 CAT
transcription regulator complex 1 AHR
external side of plasma membrane 1 CD2
Melanosome membrane 2 SLC45A2, TYR
cell-cell junction 1 CD2
Golgi-associated vesicle 1 TYR
Single-pass type II membrane protein 1 P4HTM
Mitochondrion inner membrane 1 CYP1A1
focal adhesion 1 CAT
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
Nucleus, PML body 1 MTOR
PML body 1 MTOR
receptor complex 1 PPARG
chromatin 3 AHR, MNT, PPARG
nuclear envelope 1 MTOR
Endomembrane system 1 MTOR
aryl hydrocarbon receptor complex 1 AHR
Melanosome 1 TYR
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
death-inducing signaling complex 1 CASP3
Cytoplasmic vesicle, phagosome 1 MTOR
catalase complex 1 CAT
nuclear aryl hydrocarbon receptor complex 1 AHR
cytosolic aryl hydrocarbon receptor complex 1 AHR


文献列表

  • Gaëlle Magliocco, Jules Desmeules, Caroline Flora Samer, Aurélien Thomas, Youssef Daali. Evaluation of CYP1A2 activity: Relationship between the endogenous urinary 6-hydroxymelatonin to melatonin ratio and paraxanthine to caffeine ratio in dried blood spots. Clinical and translational science. 2022 06; 15(6):1482-1491. doi: 10.1111/cts.13263. [PMID: 35338582]
  • Seiya Ohki, Miyu Kunimatsu, Shingo Ogawa, Hiroki Takano, Tomomi Furihata, Hiromi Shibasaki, Akitomo Yokokawa. Development and Validation of an LC-MS/MS-Based Method for Quantifying Urinary Endogenous 6-Hydroxymelatonin. Chemical & pharmaceutical bulletin. 2022; 70(5):375-382. doi: 10.1248/cpb.c21-00982. [PMID: 35491194]
  • G Magliocco, F Le Bloc'h, A Thomas, J Desmeules, Y Daali. Simultaneous determination of melatonin and 6-hydroxymelatonin in human overnight urine by LC-MS/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2021 Sep; 1181(?):122938. doi: 10.1016/j.jchromb.2021.122938. [PMID: 34521018]
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  • Huimin Zhao, Yifei Wang, Bo Yuan, Shu Liu, Shuang Man, Haiyan Xu, Xiumei Lu. A novel LC-MS/MS assay for the simultaneous determination of melatonin and its two major metabolites, 6-hydroxymelatonin and 6-sulfatoxymelatonin in dog plasma: Application to a pharmacokinetic study. Journal of pharmaceutical and biomedical analysis. 2016 Jan; 117(?):390-7. doi: 10.1016/j.jpba.2015.09.028. [PMID: 26440286]
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  • Yeong Byeon, Dun-Xian Tan, Russel J Reiter, Kyoungwhan Back. Predominance of 2-hydroxymelatonin over melatonin in plants. Journal of pineal research. 2015 Nov; 59(4):448-54. doi: 10.1111/jpi.12274. [PMID: 26331804]
  • Ruslán Álvarez-Diduk, Annia Galano, Dun Xian Tan, Russel J Reiter. N-Acetylserotonin and 6-Hydroxymelatonin against Oxidative Stress: Implications for the Overall Protection Exerted by Melatonin. The journal of physical chemistry. B. 2015 Jul; 119(27):8535-43. doi: 10.1021/acs.jpcb.5b04920. [PMID: 26079042]
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