beta-Carboline (BioDeep_00000002136)

 

Secondary id: BioDeep_00000397990, BioDeep_00000407563

human metabolite PANOMIX_OTCML-2023 Endogenous


代谢物信息卡片


Norharman hydrochloride

化学式: C11H8N2 (168.0687)
中文名称: 9H-吡啶[3,4-b]吲哚
谱图信息: 最多检出来源 Viridiplantae(plant) 10.09%

分子结构信息

SMILES: C1=CC=C2C(=C1)C3=C(N2)C=NC=C3
InChI: InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H

描述信息

beta-Carboline, also known as norharmane, is an organic amine and is the prototype of a class of compounds known as beta-carbolines. beta-Carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. beta-Carboline is a very strong basic compound (based on its pKa). beta-Carboline alkaloids are widely distributed in plants and animals and many are inverse agonists of the GABA-A receptor complex (PMID: 17334612). Other biological activities demonstrated by these compounds include intercalation; inhibition of CDK, topoisomerase, and monoamine oxidase; and interaction with 5-hydroxy serotonin receptors. These compounds have also exhibited sedative, anxiolytic, hypnotic, anticonvulsant, antitumor, antiviral, antiparasitic, and antimicrobial activities (PMID: 17305548).
b-Carboline (9H-pyrido[3,4-b]indole) is an organic amine that is the prototype of a class of compounds known as b-carbolines. [HMDB]. Norharman is found in chicory.
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 75
CONFIDENCE standard compound; INTERNAL_ID 2883
D009676 - Noxae > D009498 - Neurotoxins
D009676 - Noxae > D009153 - Mutagens
Norharmane (Norharman), a β-carboline alkaloid, is a potent and reversible monoamine oxidase inhibitor, with IC50 values of 6.5 and 4.7 μM for MAO-A and MAO-B, respectively. Norharmane causes antidepressant responses. Norharmane is also a prospective anti-cancer photosensitizer. Norharmane alters polar auxin transport (PAT) by inhibiting PIN2, PIN3 and PIN7 transport proteins, thus causing a significant inhibitory effect on the growth of Arabidopsis thaliana seedlings[1][2][3][4][5][6].
Norharmane (Norharman), a β-carboline alkaloid, is a potent and reversible monoamine oxidase inhibitor, with IC50 values of 6.5 and 4.7 μM for MAO-A and MAO-B, respectively. Norharmane causes antidepressant responses. Norharmane is also a prospective anti-cancer photosensitizer. Norharmane alters polar auxin transport (PAT) by inhibiting PIN2, PIN3 and PIN7 transport proteins, thus causing a significant inhibitory effect on the growth of Arabidopsis thaliana seedlings[1][2][3][4][5][6].

同义名列表

15 个代谢物同义名

Norharman hydrochloride; 9H-Pyrido(3,4-b)indole; 9H-Pyrido[3,4-B]indole; 2,9-Diazafluorene; 9H-beta-Carboline; beta-Carboline; 9H-b-Carboline; 2-Azacarbazole; 9H-Β-carboline; Β-carboline; Carbazoline; b-Carboline; Norharmane; Norhormane; Norharman



数据库引用编号

24 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)

51 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 13 ANXA5, BCL2, BDNF, CASP3, CDK2, CTNNB1, CYP1A1, DYRK1A, HDAC6, MAPK14, MTOR, PTGS2, SGCB
Peripheral membrane protein 6 ACHE, ANXA5, CYP1A1, CYP1B1, MTOR, PTGS2
Endoplasmic reticulum membrane 5 BCL2, CYP1A1, CYP1B1, MTOR, PTGS2
Mitochondrion membrane 1 MAOA
Nucleus 10 ACHE, BCL2, CASP3, CDK2, CTNNB1, DYRK1A, HDAC6, MAPK14, MTOR, TOP1
cytosol 9 ANXA5, BCL2, CASP3, CDK2, CTNNB1, HDAC6, MAOA, MAPK14, MTOR
dendrite 4 BDNF, DYRK1A, HDAC6, MTOR
phagocytic vesicle 1 MTOR
centrosome 3 CDK2, CTNNB1, HDAC6
nucleoplasm 8 CASP3, CDK2, CTNNB1, DYRK1A, HDAC6, MAPK14, MTOR, TOP1
Cell membrane 3 ACHE, CTNNB1, TNF
Cytoplasmic side 2 MAOA, MTOR
lamellipodium 1 CTNNB1
Cell projection, axon 1 HDAC6
Golgi apparatus membrane 1 MTOR
Synapse 2 ACHE, CTNNB1
cell cortex 1 CTNNB1
cell junction 1 CTNNB1
cell surface 2 ACHE, TNF
glutamatergic synapse 3 CASP3, CTNNB1, MAPK14
Golgi apparatus 1 ACHE
Golgi membrane 1 MTOR
lysosomal membrane 1 MTOR
mitochondrial inner membrane 1 CYP1A1
neuromuscular junction 1 ACHE
neuronal cell body 2 CASP3, TNF
presynaptic membrane 1 CTNNB1
sarcolemma 2 ANXA5, SGCB
synaptic vesicle 1 BDNF
Lysosome 1 MTOR
endosome 1 CDK2
plasma membrane 5 ACHE, BCHE, CTNNB1, SGCB, TNF
Membrane 8 ACHE, ANXA5, BCL2, BDNF, CTNNB1, CYP1B1, MAOA, MTOR
axon 3 BDNF, DYRK1A, HDAC6
basolateral plasma membrane 1 CTNNB1
caveola 2 HDAC6, PTGS2
extracellular exosome 2 ANXA5, CTNNB1
Lysosome membrane 1 MTOR
endoplasmic reticulum 2 BCL2, PTGS2
extracellular space 5 ACHE, BCHE, BDNF, IL6, TNF
perinuclear region of cytoplasm 4 ACHE, BDNF, CTNNB1, HDAC6
Schaffer collateral - CA1 synapse 1 CTNNB1
adherens junction 1 CTNNB1
apicolateral plasma membrane 1 CTNNB1
bicellular tight junction 1 CTNNB1
mitochondrion 5 BCL2, CYP1A1, CYP1B1, MAOA, MAPK14
protein-containing complex 3 BCL2, CTNNB1, PTGS2
intracellular membrane-bounded organelle 2 CYP1A1, CYP1B1
Microsome membrane 4 CYP1A1, CYP1B1, MTOR, PTGS2
postsynaptic density 1 CASP3
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Secreted 4 ACHE, BCHE, BDNF, IL6
extracellular region 7 ACHE, ANXA5, BCHE, BDNF, IL6, MAPK14, TNF
Mitochondrion outer membrane 3 BCL2, MAOA, MTOR
Single-pass membrane protein 2 BCL2, MAOA
mitochondrial outer membrane 3 BCL2, MAOA, MTOR
Extracellular side 1 ACHE
transcription regulator complex 2 CDK2, CTNNB1
Cell projection, cilium 1 HDAC6
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 2 CDK2, HDAC6
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 2 ANXA5, TNF
multivesicular body 1 HDAC6
perikaryon 2 HDAC6, TOP1
Z disc 1 CTNNB1
beta-catenin destruction complex 1 CTNNB1
nucleolus 1 TOP1
Wnt signalosome 1 CTNNB1
axon cytoplasm 1 HDAC6
P-body 1 TOP1
apical part of cell 1 CTNNB1
cell-cell junction 1 CTNNB1
recycling endosome 1 TNF
Single-pass type II membrane protein 2 SGCB, TNF
postsynaptic membrane 1 CTNNB1
Cell membrane, sarcolemma 1 SGCB
Mitochondrion inner membrane 1 CYP1A1
Membrane raft 1 TNF
pore complex 1 BCL2
Cytoplasm, cytoskeleton 3 CTNNB1, HDAC6, SGCB
focal adhesion 2 ANXA5, CTNNB1
microtubule 1 HDAC6
Cell junction, adherens junction 1 CTNNB1
flotillin complex 1 CTNNB1
basement membrane 1 ACHE
Nucleus, PML body 1 MTOR
PML body 1 MTOR
collagen-containing extracellular matrix 1 ANXA5
fascia adherens 1 CTNNB1
lateral plasma membrane 1 CTNNB1
nuclear speck 2 DYRK1A, MAPK14
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Zymogen granule membrane 1 ANXA5
neuron projection 1 PTGS2
ciliary basal body 1 HDAC6
cell leading edge 1 HDAC6
microtubule associated complex 1 HDAC6
phagocytic cup 1 TNF
cell periphery 1 CTNNB1
Chromosome 1 TOP1
cytoskeleton 2 DYRK1A, SGCB
Cytoplasm, cytoskeleton, cilium basal body 2 CTNNB1, HDAC6
Nucleus, nucleolus 1 TOP1
spindle pole 2 CTNNB1, MAPK14
chromosome, telomeric region 1 CDK2
blood microparticle 1 BCHE
postsynaptic density, intracellular component 1 CTNNB1
Lipid-anchor, GPI-anchor 1 ACHE
microvillus membrane 1 CTNNB1
fibrillar center 1 TOP1
nuclear envelope 2 CDK2, MTOR
Endomembrane system 2 CTNNB1, MTOR
Nucleus, nucleoplasm 1 TOP1
Cell projection, dendrite 1 HDAC6
Nucleus speckle 1 DYRK1A
euchromatin 1 CTNNB1
side of membrane 1 ACHE
myelin sheath 1 BCL2
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 1 MAPK14
endoplasmic reticulum lumen 4 BCHE, BDNF, IL6, PTGS2
male germ cell nucleus 2 CDK2, TOP1
histone deacetylase complex 1 HDAC6
beta-catenin-TCF complex 1 CTNNB1
aggresome 1 HDAC6
Single-pass type IV membrane protein 1 MAOA
nuclear envelope lumen 1 BCHE
presynaptic active zone cytoplasmic component 1 CTNNB1
vesicle membrane 1 ANXA5
Cajal body 1 CDK2
ribonucleoprotein complex 1 DYRK1A
synaptic cleft 1 ACHE
protein-DNA complex 2 CTNNB1, TOP1
death-inducing signaling complex 1 CASP3
dystrophin-associated glycoprotein complex 1 SGCB
sarcoglycan complex 1 SGCB
condensed chromosome 1 CDK2
Cytoplasmic vesicle, phagosome 1 MTOR
catenin complex 1 CTNNB1
Nucleus, Cajal body 1 CDK2
X chromosome 1 CDK2
Y chromosome 1 CDK2
cyclin-dependent protein kinase holoenzyme complex 1 CDK2
cyclin E1-CDK2 complex 1 CDK2
cyclin E2-CDK2 complex 1 CDK2
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
inclusion body 1 HDAC6
interleukin-6 receptor complex 1 IL6
endothelial microparticle 1 ANXA5
BAD-BCL-2 complex 1 BCL2
beta-catenin-TCF7L2 complex 1 CTNNB1
cyclin A2-CDK2 complex 1 CDK2
[Isoform H]: Cell membrane 1 ACHE
[Neurotrophic factor BDNF precursor form]: Secreted 1 BDNF
cyclin A1-CDK2 complex 1 CDK2
beta-catenin-ICAT complex 1 CTNNB1
Scrib-APC-beta-catenin complex 1 CTNNB1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Phumudzo P Tshikhudo, Tafadzwanashe Mabhaudhi, Neil A Koorbanally, Fhatuwani N Mudau, Edgardo Oscar Avendaño Caceres, Dragos Popa, Daniela Calina, Javad Sharifi-Rad. Anticancer Potential of β-Carboline Alkaloids: An Updated Mechanistic Overview. Chemistry & biodiversity. 2023 Dec; ?(?):e202301263. doi: 10.1002/cbdv.202301263. [PMID: 38108650]
  • Qi Zhou, Xufeng Tao, Fangyue Guo, Yu Wu, Dawei Deng, Linlin Lv, Deshi Dong, Dong Shang, Hong Xiang. Tryptophan metabolite norharman secreted by cultivated Lactobacillus attenuates acute pancreatitis as an antagonist of histone deacetylases. BMC medicine. 2023 Aug; 21(1):329. doi: 10.1186/s12916-023-02997-2. [PMID: 37635214]
  • Tao Sheng, Chenjie Yu, Yujie Wang, Shengkun Li, Huijun Wu, Qin Gu, Guangrong Meng, Alastair N Herron, Xuewen Gao. Chromatography-Free Synthesis of β-Carboline 1-Hydrazides and an Investigation of the Mechanism of Their Bioactivity: The Discovery of β-Carbolines as Promising Antifungal and Antibacterial Candidates. Journal of medicinal chemistry. 2023 07; 66(13):9040-9056. doi: 10.1021/acs.jmedchem.3c00650. [PMID: 37314697]
  • Tomás Herraiz. β-Carboline Alkaloids in Soy Sauce and Inhibition of Monoamine Oxidase (MAO). Molecules (Basel, Switzerland). 2023 Mar; 28(6):. doi: 10.3390/molecules28062723. [PMID: 36985694]
  • Yuanyuan Wang, Maofeng Dong, Limin Guo, Yamin Zhu, Qingqing Jiang, Jianbo Xiao, Mingfu Wang, Yueliang Zhao. Effect of acrolein on the formation of harman and norharman in chemical models and roast beef patties. Food research international (Ottawa, Ont.). 2023 02; 164(?):112465. doi: 10.1016/j.foodres.2023.112465. [PMID: 36738015]
  • Huiya Ma, Hongzhi Yu, Zhengyang Li, Zhi Cao, Youwei Du, Jiangkun Dai, Dongming Zhi, Yujie Xu, Na Li, Junru Wang. β-Carboline dimers inhibit the tumor proliferation by the cell cycle arrest of sarcoma through intercalating to Cyclin-A2. Frontiers in immunology. 2022; 13(?):922183. doi: 10.3389/fimmu.2022.922183. [PMID: 36325324]
  • Wei Liu, Zhaoyu Yang, Lili Shi, Ziyu Cui, Yun Li. Degradation of β-Carbolines Harman and Norharman in Edible Oils during Heating. Molecules (Basel, Switzerland). 2021 Nov; 26(22):. doi: 10.3390/molecules26227018. [PMID: 34834111]
  • Bo Luo, Xinqiang Song. A comprehensive overview of β-carbolines and its derivatives as anticancer agents. European journal of medicinal chemistry. 2021 Nov; 224(?):113688. doi: 10.1016/j.ejmech.2021.113688. [PMID: 34332400]
  • Cheng-Peng Sun, Jing Yi, Fan Wei, Xia Lv, Sa Deng, Bao-Jing Zhang, Wen-Yu Zhao, Xiao-Chi Ma. UV-light-driven photooxidation of harmaline catalyzed by riboflavin: Product characterization and mechanisms. Fitoterapia. 2021 Nov; 155(?):105054. doi: 10.1016/j.fitote.2021.105054. [PMID: 34626737]
  • Andrew B Hawkey, Julia Hoeng, Manuel C Peitsch, Edward D Levin, Kyoko Koshibu. Subchronic effects of plant alkaloids on anxiety-like behavior in zebrafish. Pharmacology, biochemistry, and behavior. 2021 08; 207(?):173223. doi: 10.1016/j.pbb.2021.173223. [PMID: 34197843]
  • Yuxiang Fan, Fanye Zeng, Lili Ma, Hongliang Zhang. Effects of β-carboline alkaloids from Peganum harmala on the FAK/PI3K/AKT/Mtor pathway in human gastric cancer cell line SGC-7901 and tumor-bearing mice. Pakistan journal of pharmaceutical sciences. 2021 May; 34(3):891-898. doi: . [PMID: 34602411]
  • Walaa Alharbi, Iftekhar Hassan, Rais Ahmad Khan, Shazia Parveen, Khadijah H Alharbi, Ibtisam I Bin Sharfan, Ibrahim M Alhazza, Hossam Ebaid, Ali Alsalme. Bioactive Tryptophan-Based Copper Complex with Auxiliary β-Carboline Spectacle Potential on Human Breast Cancer Cells: In Vitro and In Vivo Studies. Molecules (Basel, Switzerland). 2021 Mar; 26(6):. doi: 10.3390/molecules26061606. [PMID: 33799355]
  • Hyojik Yang, Shelley N Jackson, Amina S Woods, David R Goodlett, Robert K Ernst, Alison J Scott. Streamlined Analysis of Cardiolipins in Prokaryotic and Eukaryotic Samples Using a Norharmane Matrix by MALDI-MSI. Journal of the American Society for Mass Spectrometry. 2020 Dec; 31(12):2495-2502. doi: 10.1021/jasms.0c00201. [PMID: 32924474]
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