5-Methoxytryptophol (BioDeep_00000018445)
Secondary id: BioDeep_00000405479, BioDeep_00000604145
human metabolite PANOMIX_OTCML-2023 Endogenous blood metabolite Volatile Flavor Compounds
代谢物信息卡片
化学式: C11H13NO2 (191.09462380000002)
中文名称: 5-甲氧色氨酸, 5-甲氧基色氨酸
谱图信息:
最多检出来源 Homo sapiens(blood) 0.03%
分子结构信息
SMILES: COC1=CC2=C(C=C1)NC=C2CCO
InChI: InChI=1S/C11H13NO2/c1-14-9-2-3-11-10(6-9)8(4-5-13)7-12-11/h2-3,6-7,12-13H,4-5H2,1H3
描述信息
5-Methoxytryptophol is synthesized by the pineal gland. Daily rhythms in pineal methoxyindole metabolism have been described in rodents and humans (5-Methoxytryptophol levels are coincident with serotonin levels in rodents pineal) and 5-Methoxytryptophol at its highest during the daylight hours and fall markedly soon after the onset of darkness, coincident with increases in the levels of pineal melatonin and the activities of pineal serotonin-N-acetyltransferase (EC 2.3.1.87, SNAT) and hydroxyindole-O-methyltransferase (EC 2.1.1.4, HIOMT). The fact that the levels of 5-methoxytryptophol and melatonin vary in parallel suggests that the major factor generating the methoxyindole rhythms is not SNAT activity, but perhaps a change in the availability (for metabolism) of "stored" serotonin. When the onset of darkness is delayed by 12 hours, human 5-methoxytryptophol (and melatonin) rhythms usually require 3 or 4 days to adjust to the new lighting regimen. Environmental factors, other than light, that activate the sympathetic nervous system or cause epinephrine to be secreted from the adrenal medulla (e.g., the stress of immobilization; insulin-induced hypoglycemia) can override the inhibitory effects of light and accelerate melatonin synthesis. Rhythms in 5-methoxytryptophol (and melatonin) synthesis apparently persist among animals placed in environments of continuous darkness; the source of the cyclic signal (mediated by the pineal sympathetic nerves) has not yet been identified. Preliminary evidence suggests that levels of a peptide hormone, arginine vasotocin, in rat pineal and sera also exhibit daily rhythms and are increased by norepinephrine. The circadian rhythm of melatonin secretion is generated in the suprachiasmatic nucleus. Sleep disruption, nightly restlessness, sundowning, and other circadian disturbances are frequently seen in Alzheimers disease patients. Changes in the suprachiasmatic nucleus and pineal gland are thought to be the biological basis for these behavioral disturbances. (PMID 288858, 2245336) [HMDB]
5-Methoxytryptophol is synthesized by the pineal gland. Daily rhythms in pineal methoxyindole metabolism have been described in rodents and humans (5-Methoxytryptophol levels are coincident with serotonin levels in rodents pineal) and 5-Methoxytryptophol at its highest during the daylight hours and fall markedly soon after the onset of darkness, coincident with increases in the levels of pineal melatonin and the activities of pineal serotonin-N-acetyltransferase (EC 2.3.1.87, SNAT) and hydroxyindole-O-methyltransferase (EC 2.1.1.4, HIOMT). The fact that the levels of 5-methoxytryptophol and melatonin vary in parallel suggests that the major factor generating the methoxyindole rhythms is not SNAT activity, but perhaps a change in the availability (for metabolism) of "stored" serotonin. When the onset of darkness is delayed by 12 hours, human 5-methoxytryptophol (and melatonin) rhythms usually require 3 or 4 days to adjust to the new lighting regimen. Environmental factors, other than light, that activate the sympathetic nervous system or cause epinephrine to be secreted from the adrenal medulla (e.g., the stress of immobilization; insulin-induced hypoglycemia) can override the inhibitory effects of light and accelerate melatonin synthesis. Rhythms in 5-methoxytryptophol (and melatonin) synthesis apparently persist among animals placed in environments of continuous darkness; the source of the cyclic signal (mediated by the pineal sympathetic nerves) has not yet been identified. Preliminary evidence suggests that levels of a peptide hormone, arginine vasotocin, in rat pineal and sera also exhibit daily rhythms and are increased by norepinephrine. The circadian rhythm of melatonin secretion is generated in the suprachiasmatic nucleus. Sleep disruption, nightly restlessness, sundowning, and other circadian disturbances are frequently seen in Alzheimers disease patients. Changes in the suprachiasmatic nucleus and pineal gland are thought to be the biological basis for these behavioral disturbances. (PMID 288858, 2245336).
D002492 - Central Nervous System Depressants > D014149 - Tranquilizing Agents > D014151 - Anti-Anxiety Agents
D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents
D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants
5-Methoxytryptophol is a natural indole present in the pineal gland.
同义名列表
数据库引用编号
11 个数据库交叉引用编号
- ChEBI: CHEBI:89851
- PubChem: 12835
- HMDB: HMDB0001896
- ChEMBL: CHEMBL14485
- Wikipedia: Tryptophol
- foodb: FDB022726
- chemspider: 12305
- CAS: 712-09-4
- PMhub: MS000008027
- RefMet: 5-Methoxytryptophol
- medchemexpress: HY-113440
分类词条
相关代谢途径
Reactome(0)
BioCyc(3)
PlantCyc(0)
代谢反应
5 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(5)
- superpathway of tryptophan utilization:
N-formylkynurenine + H2O ⟶ H+ + L-kynurenine + formate
- superpathway of melatonin degradation:
hydrogen peroxide + melatonin ⟶ N1-acetyl-N2-formyl-5-methoxykynuramine + H2O
- melatonin degradation II:
5-methoxytryptamine + H+ + H2O + O2 ⟶ 5-methoxyindoleacetaldehyde + ammonium + hydrogen peroxide
- superpathway of melatonin degradation:
N1-acetyl-N2-formyl-5-methoxykynuramine + H2O ⟶ N-acetyl-5-methoxykynurenamine + H+ + formate
- melatonin degradation II:
5-methoxyindoleacetaldehyde + A(H2) ⟶ 5-methoxytryptophol + A
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。
文献列表
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Cell reports.
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1996 Sep; 21(2):73-9. doi:
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Journal of biological regulators and homeostatic agents.
1996 Jan; 10(1):27-30. doi:
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Journal of neural transmission. General section.
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Neuroscience letters.
1990 Jan; 108(1-2):138-42. doi:
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Clinical chemistry.
1989 Aug; 35(8):1749-52. doi:
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1986 Jul; 110(1):177-84. doi:
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