5-Hydroxytryptophan (BioDeep_00000000221)

Main id: BioDeep_00000000117

Secondary id: BioDeep_00000402917

PANOMIX_OTCML-2023


代谢物信息卡片


(S)-2-Amino-3-(5-hydroxy-1H-indol-3-yl)-propionic acid;C5-Hydroxy-L-tryptophan;5-HTP;Oxitriptan

化学式: C11H12N2O3 (220.0848)
中文名称: 5-羟基色氨酸, DL-5-羟色氨酸, 5-羟色氨酸, DL-5-羟基色氨酸
谱图信息: 最多检出来源 Viridiplantae(plant) 64.95%

分子结构信息

SMILES: C1=CC2=C(C=C1O)C(=CN2)CC(C(=O)O)N
InChI: InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)

描述信息

5-hydroxytryptophan is a tryptophan derivative that is tryptophan substituted by a hydroxy group at position 5. It has a role as a human metabolite and a neurotransmitter.
5-Hydroxytryptophan, DL- is a racemic mixture of 5-hydroxytryptophan (5-HTP), a precursor to the neurotransmitter serotonin with anti-depressant, analgesic and appetite-suppressant activities. DL-5-HTP is decarboxylated to serotonin by aromatic-L-amino-acid decarboxylase, and results in increased serotonin levels within the brain. Mediated through serotonin receptors, elevated levels of serotonin causes increased serotonin neurotransmissions, hence leading to release of depression, pain and appetite.
5-Hydroxy-L-tryptophan is an aromatic amino acid naturally produced by the body from the essential amino acid l-tryptophan. 5-Hydroxy-L-tryptophan is the immediate precursor of the neurotransmitter serotonin. The conversion to serotonin is catalyzed by the enzyme aromatic l-amino acid decarboxylase (EC 4.1.1.28, AADC1 also known as dopa decarboxylase), an essential enzyme in the metabolism of the monoamine neurotransmitters. An accumulation of 5-Hydroxy-L-tryptophan in cerebrospinal fluid occurs in Aromatic l-amino acid decarboxylase deficiency (OMIM 608643), accompanied by an increased excretion in the urine of the patients, which are indicative of the disorder but not specific 5-Hydroxy-L-tryptophan is also increased in other disorders such as in Parkinsons patients with severe postural instability and gait disorders. Confirmation of the diagnosis AADC deficiency is then required by enzyme activity measurement or genetic analysis. The amount of endogenous 5-Hydroxy-L-tryptophan available for serotonin synthesis depends on the availability of tryptophan and on the activity of various enzymes, especially tryptophan hydroxylase (EC 1.14.16.4), indoleamine 2,3-dioxygenase (EC 1.13.11.52), and tryptophan 2,3-dioxygenase. (EC 1.13.11.11, TDO). 5-Hydroxy-L-tryptophan has been used clinically for over 30 years. In addition to depression, the therapeutic administration of 5-Hydroxy-L-tryptophan has been shown to be effective in treating a wide variety of conditions, including fibromyalgia, insomnia, binge eating associated with obesity, cerebellar ataxia, and chronic headaches. 5-Hydroxy-L-tryptophan easily crosses the blood-brain barrier and effectively increases central nervous system (CNS) synthesis of serotonin. Supplementation with 5-Hydroxy-L-tryptophan is hypothesized to normalize serotonin synthesis, which is putatively related to its antidepressant properties. (A3384, A3385, A3386).
The immediate precursor in the biosynthesis of SEROTONIN from tryptophan. It is used as an antiepileptic and antidepressant.
D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D000928 - Antidepressive Agents
A tryptophan derivative that is tryptophan substituted by a hydroxy group at position 5.
5-Hydroxytryptophan, a tryptophan metabolite, is a direct 5-hydroxytryptamine (5-HT) precursor and an L-aromatic amino acid decarboxylase substrate. [1][2][3].
5-Hydroxytryptophan, a tryptophan metabolite, is a direct 5-hydroxytryptamine (5-HT) precursor and an L-aromatic amino acid decarboxylase substrate. [1][2][3].

同义名列表

46 个代谢物同义名

(S)-2-Amino-3-(5-hydroxy-1H-indol-3-yl)-propionic acid;C5-Hydroxy-L-tryptophan;5-HTP;Oxitriptan; 2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid; 2-Amino-3-(5-hydroxy-1H-indol-3-yl)propanoicacid; DL-2-Amino-3-(5-hydroxyindolyl)propionic acid; 5-22-14-00278 (Beilstein Handbook Reference); 5-Hydroxytryptophan, AldrichCPR; 5-hydroxytryptophan (5-HTP); 5-Hydroxytryptophan DL-form; 5-HYDROXYTRYPTOPHAN [HSDB]; 5-Hydroxytryptophan L form; (.+-.)-5-Hydroxytryptophan; Tryptophan, 5-hydroxy-, dl; Tryptophan, 5-hydroxy-, L-; 5-hydroxytryptophan(5-HTP); DL-Tryptophan, 5-hydroxy-; (+/-)-5-Hydroxytryptophan; (+-)-5-Hydroxytryptophan; 5-HYDROXYTRYPTOPHAN [MI]; 5-hydroxytryptophan, dl-; D,L-5-hydroxytryptophan; dl-5-Hydroxytryptophane; 5-Hydroxy-DL-tryptophan; 5-Hydroxy-D-tryptophan; 5-hydroxy l-tryptophan; WLN: T56 BMJ D1YZVQ GQ; DL-5-Hydroxytryptophan; Tryptophan, 5-hydroxy-; 5-Hydroxy- Tryptophan; 5-Hydroxytryptophan #; Tryptophan, 5 Hydroxy; DL-Hydroxytryptophan; 5-hydroxy tryptophan; 5-hydroxytryptophan; 5 Hydroxytryptophan; H-DL-Trp(5-OH)-OH; hydroxytryptophan; H-L-Trp(5-OH)-OH; Dl-oxitriptan; Oxytryptophan; DL-Pretonine; USAF CB-96; Oxitriptan; DL-5-HTP; 5-HTP; 5-Hydroxytryptophan; 5-Hydroxytryptophan



数据库引用编号

21 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

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)

2 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 AANAT, HTR4, PRL, TH
Endosome membrane 2 HTR4, SLC6A4
Mitochondrion membrane 1 MAOA
Nucleus 2 PRL, TH
cytosol 7 AANAT, MAOA, PAH, SST, TDO2, TH, TPH1
dendrite 7 HTR1A, HTR1B, HTR2A, HTR2C, HTR4, HTR7, TH
nucleoplasm 1 PRL
RNA polymerase II transcription regulator complex 1 PRL
Cell membrane 8 HTR1A, HTR1B, HTR2A, HTR2C, HTR3A, HTR4, HTR7, SLC6A4
Cytoplasmic side 1 MAOA
Cleavage furrow 1 HTR3A
Cell projection, axon 2 HTR2A, TH
Multi-pass membrane protein 8 HTR1A, HTR1B, HTR2A, HTR2C, HTR3A, HTR4, HTR7, SLC6A4
Synapse 6 HTR1A, HTR2C, HTR3A, HTR4, HTR7, SLC6A4
dendritic shaft 1 HTR2A
glutamatergic synapse 2 HTR2A, HTR4
Golgi membrane 1 INS
neuronal cell body 2 HTR2A, SST
postsynapse 2 HTR3A, HTR4
presynaptic membrane 3 HTR1B, HTR2A, SLC6A4
smooth endoplasmic reticulum 1 TH
synaptic vesicle 1 TH
Presynapse 2 HTR2A, SLC6A4
endosome 1 HTR4
plasma membrane 9 HTR1A, HTR1B, HTR2A, HTR2C, HTR3A, HTR4, HTR7, IFNLR1, SLC6A4
terminal bouton 1 TH
Membrane 5 HTR3A, HTR4, IFNLR1, MAOA, SLC6A4
axon 2 HTR2A, TH
caveola 1 HTR2A
endoplasmic reticulum 1 HTR1B
extracellular space 4 IL6, INS, PRL, SST
perinuclear region of cytoplasm 2 AANAT, TH
mitochondrion 2 MAOA, TH
Single-pass type I membrane protein 1 IFNLR1
Secreted 5 IL6, INS, PRL, SST, TRH
extracellular region 5 IL6, INS, PRL, SST, TRH
cytoplasmic side of plasma membrane 1 TH
Mitochondrion outer membrane 1 MAOA
Single-pass membrane protein 1 MAOA
mitochondrial outer membrane 1 MAOA
perikaryon 1 TH
cytoplasmic vesicle 2 HTR2A, TH
Melanosome membrane 1 TH
postsynaptic membrane 3 HTR2A, HTR3A, SLC6A4
Cytoplasm, perinuclear region 1 TH
Membrane raft 1 SLC6A4
Cell junction, focal adhesion 1 SLC6A4
focal adhesion 1 SLC6A4
GABA-ergic synapse 1 SST
secretory granule 1 TRH
Postsynaptic cell membrane 1 HTR3A
Cell projection, neuron projection 1 SLC6A4
neuron projection 4 HTR3A, SLC6A4, TH, TPH1
chromatin 1 PRL
serotonin-activated cation-selective channel complex 1 HTR3A
transmembrane transporter complex 1 HTR3A
Endomembrane system 1 SLC6A4
endosome lumen 2 INS, PRL
Membrane, caveola 1 HTR2A
cell body fiber 1 HTR2A
Cell projection, dendrite 2 HTR1A, HTR2A
trans-Golgi network membrane 1 HTR7
secretory granule lumen 1 INS
Golgi lumen 1 INS
endoplasmic reticulum lumen 2 IL6, INS
transport vesicle 1 INS
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
neuronal dense core vesicle 1 SST
Single-pass type IV membrane protein 1 MAOA
neurofilament 1 HTR2A
calyx of Held 1 HTR1B
interleukin-6 receptor complex 1 IL6
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle 1 TH
G protein-coupled serotonin receptor complex 3 HTR1B, HTR2A, HTR2C
serotonergic synapse 2 HTR1B, SLC6A4
interleukin-28 receptor complex 1 IFNLR1


文献列表

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  • Yingying Wang, Xueman Chen, Qiaoyu Chen, Ning Zhou, Xin Wang, Alei Zhang, Kequan Chen, Pingkai Ouyang. Construction of cell factory capable of efficiently converting L-tryptophan into 5-hydroxytryptamine. Microbial cell factories. 2022 Mar; 21(1):47. doi: 10.1186/s12934-022-01745-0. [PMID: 35331215]
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  • Yuying Liu, Nannan Zhou, Li Zhou, Jing Wang, Yabo Zhou, Tianzhen Zhang, Yi Fang, Jinwei Deng, Yunfeng Gao, Xiaoyu Liang, Jiadi Lv, Zhenfeng Wang, Jing Xie, Yuanbo Xue, Huafeng Zhang, Jingwei Ma, Ke Tang, Yiliang Fang, Feiran Cheng, Chengjuan Zhang, Bing Dong, Yuzhou Zhao, Peng Yuan, Quanli Gao, Haizeng Zhang, F Xiao-Feng Qin, Bo Huang. IL-2 regulates tumor-reactive CD8+ T cell exhaustion by activating the aryl hydrocarbon receptor. Nature immunology. 2021 03; 22(3):358-369. doi: 10.1038/s41590-020-00850-9. [PMID: 33432230]
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  • Shabbir Ahmad, Mujahid Mohammed, Lakshmi Prasuna Mekala, Sasikala Chintalapati, Venkata Ramana Chintalapati. Tryptophan, a non-canonical melanin precursor: New L-tryptophan based melanin production by Rubrivivax benzoatilyticus JA2. Scientific reports. 2020 06; 10(1):8925. doi: 10.1038/s41598-020-65803-6. [PMID: 32488041]
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  • Zheng Guan, Gabriel Jacobs, Hans van Pelt, Joop M A Van Gerven, Jacobus Burggraaf, Wei Zhao. PK/PD modeling of 5-hydroxytryptophan (5-HTP) challenge test with cortisol measurement in serum and saliva. Pharmacology research & perspectives. 2020 04; 8(2):e00574. doi: 10.1002/prp2.574. [PMID: 32168433]
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