Harman (BioDeep_00000000032)

 

Secondary id: BioDeep_00000397976, BioDeep_00000865256

human metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


1-methyl-9H-pyrido[3,4-b]indole

化学式: C12H10N2 (182.0844)
中文名称: 哈尔满碱
谱图信息: 最多检出来源 Viridiplantae(plant) 10.01%

Reviewed

Last reviewed on 2024-06-29.

Cite this Page

Harman. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/harman (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000000032). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: CC1=C2NC3=CC=CC=C3C2=CC=N1
InChI: InChI=1S/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H3

描述信息

Harman is an indole alkaloid fundamental parent with a structure of 9H-beta-carboline carrying a methyl substituent at C-1. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, Passiflora incarnata, Peganum harmala, Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke. It is a specific, reversible inhibitor of monoamine oxidase A. It has a role as an anti-HIV agent, a plant metabolite and an EC 1.4.3.4 (monoamine oxidase) inhibitor. It is an indole alkaloid, an indole alkaloid fundamental parent and a harmala alkaloid.
Harman is a natural product found in Ophiopogon, Strychnos johnsonii, and other organisms with data available.
An indole alkaloid fundamental parent with a structure of 9H-beta-carboline carrying a methyl substituent at C-1. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, Passiflora incarnata, Peganum harmala, Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke. It is a specific, reversible inhibitor of monoamine oxidase A.
Isolated from roots of Panax ginseng and Codonopsis lanceolata (todok). Struct. has now been shown to be identical with 1-Acetyl-b-carboline CHK59-M
Harman is found in chicory. Harman is an alkaloid from the may pop (Passiflora incarnata, Passifloraceae) and many other Passiflora sp

[Raw Data] CB042_Harman_pos_30eV_CB000019.txt
[Raw Data] CB042_Harman_pos_20eV_CB000019.txt
[Raw Data] CB042_Harman_pos_40eV_CB000019.txt
[Raw Data] CB042_Harman_pos_10eV_CB000019.txt
[Raw Data] CB042_Harman_pos_50eV_CB000019.txt
[Raw Data] CB042_Harman_neg_50eV_000012.txt
[Raw Data] CB042_Harman_neg_30eV_000012.txt
[Raw Data] CB042_Harman_neg_40eV_000012.txt
[Raw Data] CB042_Harman_neg_20eV_000012.txt
[Raw Data] CB042_Harman_neg_10eV_000012.txt

Harman. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=486-84-0 (retrieved 2024-06-29) (CAS RN: 486-84-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4].
Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4].
Harmane, a β-Carboline alkaloid (BCA), is a potent neurotoxin that causes severe action tremors and psychiatric manifestations. Harmane shows 1000-fold selectivity for I1-Imidazoline receptor (IC50=30 nM) over α2-adrenoceptor (IC50=18 μM). Harmane is also a potent and selective inhibitor of monoamine oxidase (MAO) (IC50s=0.5 and 5 μM for human MAO A/B, respectively). Harmane exhibits comutagenic effect[1][2][3][4].

同义名列表

69 个代谢物同义名

InChI=1/C12H10N2/c1-8-12-10(6-7-13-8)9-4-2-3-5-11(9)14-12/h2-7,14H,1H; 5-23-08-00261 (Beilstein Handbook Reference); Harmane ( 1-Methyl-9H-pyrido[3,4-b]indole); 1-Methyl-9H-pyrido[3,4-b]indole, 9CI; 1-Methyl-9H-beta-carboline (Harman); 9H-Pyrido(3,4-b)indole, 1-methyl-; 9H-Pyrido[3,4-b]indole, 1-methyl-; 1-Methyl-9H-pyrido(3,4-b)indole; 1-Methyl-9H-Pyrido[3,4-6]indole; 1-Methyl-9H-pyrido[3,4-b]indole; Na-Formyl-1-methyl-b-carboline; 1-Methyl-9H-pyrid(3,4-b)indole; 1-Methyl-9H-pyrid[3,4-b]indole; 1-Methyl-9H-beta-carboline #; 1-Methyl-9H-beta-carboline; 1-Methyl-9H-I(2)-carboline; 1-Methyl-.beta.-carboline; PYRIDOBINDOLE, L-METHYL-; 2-Methyl-beta-carboline; 1-methyl-beta-carboline; 1-Methyl-9H-β-carboline; 1-Methyl-9H-b-carboline; L-Methyl-Pyridobindole; L-methylpyridobindole; 1-Methyl-b-carboline; Passiflorin-13C2,15N; 1-Methyl-β-carboline; harman hydrochloride; methylbeta-carboline; 3-Methyl-4-carboline; 1-methyl-2-carboline; Cyanoaceticacid-Osu; Harmane, free base; Prestwick3_000620; 1-Methylnorharman; Harman-d3 (Major); Prestwick2_000620; Prestwick1_000620; Prestwick0_000620; Spectrum3_000905; Spectrum4_001003; UNII-82D6J0535P; Harman-13C2,15N; Harmane, 98\\%; Lopac0_000605; DivK1c_006705; BPBio1_000616; Oprea1_152883; Tox21_500605; KBio3_001850; KBio2_001606; Passiflorine; Zygofabagine; KBio1_001649; KBio2_004174; KBio2_006742; HARMAN [MI]; Passiflorin; 82D6J0535P; Locuturine; Harman-d3; Locuturin; Loturine; Aribine; Harmane; Aribin; Harman; CN9; Harman



数据库引用编号

52 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)

283 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 7 ADIG, CA1, CA3, MAPK14, PRKAA2, SIRT1, SLC6A3
Peripheral membrane protein 2 ACHE, CYP1B1
Endoplasmic reticulum membrane 2 CYP1B1, DRD1
Mitochondrion membrane 1 MAOA
Nucleus 7 ACHE, ADIG, DRD1, MAPK14, MPO, PRKAA2, SIRT1
cytosol 6 CA1, CA3, MAOA, MAPK14, PRKAA2, SIRT1
dendrite 4 DRD2, HTR2A, MAOB, PRKAA2
nucleoplasm 4 MAPK14, MPO, PRKAA2, SIRT1
Cell membrane 5 ACHE, DRD1, DRD2, HTR2A, SLC6A3
Cytoplasmic side 2 MAOA, MAOB
Cell projection, axon 2 HTR2A, SLC6A3
Multi-pass membrane protein 6 CACNA1I, DRD1, DRD2, HTR2A, RYR2, SLC6A3
Golgi apparatus membrane 1 DRD2
Synapse 2 ACHE, DRD2
cell surface 2 ACHE, SLC6A3
dendritic shaft 1 HTR2A
glutamatergic synapse 4 DRD1, DRD2, HTR2A, MAPK14
Golgi apparatus 2 ACHE, PRKAA2
Golgi membrane 2 DRD2, INS
neuromuscular junction 1 ACHE
neuronal cell body 4 HTR2A, MAOB, PRKAA2, SLC6A3
presynaptic membrane 4 DRD1, DRD2, HTR2A, SLC6A3
sarcolemma 1 RYR2
smooth endoplasmic reticulum 1 RYR2
Lysosome 1 MPO
Presynapse 1 HTR2A
acrosomal vesicle 1 DRD2
plasma membrane 9 ACHE, BCHE, CACNA1I, DRD1, DRD2, F2, HTR2A, RYR2, SLC6A3
synaptic vesicle membrane 1 DRD2
Membrane 8 ACHE, ADIG, CACNA1I, CYP1B1, MAOA, PRKAA2, RYR2, SLC6A3
axon 4 DRD2, HTR2A, PRKAA2, SLC6A3
caveola 1 HTR2A
extracellular exosome 3 CA1, F2, MPO
extracellular space 5 ACHE, BCHE, F2, INS, MPO
perinuclear region of cytoplasm 1 ACHE
mitochondrion 5 CYP1B1, MAOA, MAOB, MAPK14, SIRT1
protein-containing complex 1 RYR2
intracellular membrane-bounded organelle 2 CYP1B1, MPO
Microsome membrane 1 CYP1B1
chromatin silencing complex 1 SIRT1
Secreted 5 ACHE, ADIG, BCHE, F2, INS
extracellular region 7 ACHE, ADIG, BCHE, F2, INS, MAPK14, MPO
Mitochondrion outer membrane 2 MAOA, MAOB
Single-pass membrane protein 2 ADIG, MAOA
mitochondrial outer membrane 2 MAOA, MAOB
neuronal cell body membrane 1 SLC6A3
Extracellular side 1 ACHE
ciliary membrane 2 DRD1, DRD2
dendritic spine 2 DRD1, DRD2
perikaryon 1 DRD2
Z disc 1 RYR2
cytoplasmic vesicle 1 HTR2A
nucleolus 1 SIRT1
postsynaptic membrane 4 DRD1, DRD2, HTR2A, SLC6A3
heterochromatin 1 SIRT1
Membrane raft 1 SLC6A3
GABA-ergic synapse 2 DRD1, DRD2
flotillin complex 1 SLC6A3
basement membrane 1 ACHE
sarcoplasmic reticulum 1 RYR2
Cell projection, dendritic spine 1 DRD1
Nucleus, PML body 1 SIRT1
PML body 1 SIRT1
collagen-containing extracellular matrix 1 F2
secretory granule 1 MPO
lateral plasma membrane 1 DRD2
nuclear speck 2 MAPK14, PRKAA2
nuclear inner membrane 1 SIRT1
Cell projection, neuron projection 1 SLC6A3
neuron projection 1 SLC6A3
cilium 2 DRD1, DRD2
chromatin 1 SIRT1
spindle pole 1 MAPK14
blood microparticle 2 BCHE, F2
non-motile cilium 2 DRD1, DRD2
Lipid-anchor, GPI-anchor 1 ACHE
sperm flagellum 1 DRD2
fibrillar center 1 SIRT1
nuclear envelope 1 SIRT1
endosome lumen 1 INS
Lipid droplet 1 ADIG
Membrane, caveola 1 HTR2A
cell body fiber 1 HTR2A
Cell projection, dendrite 2 DRD1, HTR2A
cytoplasmic stress granule 1 PRKAA2
euchromatin 1 SIRT1
side of membrane 1 ACHE
azurophil granule 1 MPO
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 2 INS, MAPK14
Golgi lumen 2 F2, INS
endoplasmic reticulum lumen 3 BCHE, F2, INS
axon terminus 2 DRD2, SLC6A3
voltage-gated calcium channel complex 1 CACNA1I
endocytic vesicle 1 DRD2
transport vesicle 1 INS
azurophil granule lumen 1 MPO
Sarcoplasmic reticulum membrane 1 RYR2
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 INS
mitochondrial envelope 1 MAOB
Single-pass type IV membrane protein 2 MAOA, MAOB
nuclear envelope lumen 1 BCHE
neurofilament 1 HTR2A
calcium channel complex 1 RYR2
junctional sarcoplasmic reticulum membrane 1 RYR2
phagocytic vesicle lumen 1 MPO
synaptic cleft 1 ACHE
eNoSc complex 1 SIRT1
rDNA heterochromatin 1 SIRT1
dopaminergic synapse 2 DRD2, SLC6A3
nucleotide-activated protein kinase complex 1 PRKAA2
Cell projection, cilium membrane 1 DRD1
G protein-coupled receptor complex 2 DRD1, DRD2
[Isoform H]: Cell membrane 1 ACHE
G protein-coupled serotonin receptor complex 1 HTR2A
[SirtT1 75 kDa fragment]: Cytoplasm 1 SIRT1


文献列表

  • Bao Tan Nguyen, Nguyen Thi Hai Yen, Ninh Khac Thanh Tung, Gil-Saeng Jeong, Jong Seong Kang, Nguyen Phuoc Long, Hyung Min Kim. Lipid class-dependent alterations of Caenorhabditis elegans under harmane exposure. Journal of pharmaceutical and biomedical analysis. 2023 Jul; 231(?):115401. doi: 10.1016/j.jpba.2023.115401. [PMID: 37105045]
  • Soching Luikham, Mavani A, Jhimli Bhattacharyya. Deciphering binding affinity, energetics, and base specificity of plant alkaloid Harmane with AT and GC hairpin duplex DNA. Luminescence : the journal of biological and chemical luminescence. 2022 May; 37(5):691-701. doi: 10.1002/bio.4210. [PMID: 35156295]
  • 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]
  • 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]
  • Vivek Lawana, Se Young Um, Rachel M Foguth, Jason R Cannon. Neuromelanin formation exacerbates HAA-induced mitochondrial toxicity and mitophagy impairments. Neurotoxicology. 2020 12; 81(?):147-160. doi: 10.1016/j.neuro.2020.10.005. [PMID: 33058929]
  • Chen-Xia Zhang, Jun Xi, Tian-Pei Zhao, Yu-Xiang Ma, Xue-De Wang. β-carbolines norharman and harman in vegetable oils in China. Food additives & contaminants. Part B, Surveillance. 2020 Sep; 13(3):193-199. doi: 10.1080/19393210.2020.1759701. [PMID: 32364007]
  • Renata Zawirska-Wojtasiak, Agnieszka Fedoruk-Wyszomirska, Paulina Piechowska, Sylwia Mildner-Szkudlarz, Joanna Bajerska, Elżbieta Wojtowicz, Krzysztof Przygoński, Dorota Gurda, Wiktoria Kubicka, Eliza Wyszko. β-Carbolines in Experiments on Laboratory Animals. International journal of molecular sciences. 2020 Jul; 21(15):. doi: 10.3390/ijms21155245. [PMID: 32722000]
  • Falco Beer, Felix Urbat, Charles M A P Franz, Melanie Huch, Sabine E Kulling, Mirko Bunzel, Diana Bunzel. The Human Fecal Microbiota Metabolizes Foodborne Heterocyclic Aromatic Amines by Reuterin Conjugation and Further Transformations. Molecular nutrition & food research. 2019 05; 63(10):e1801177. doi: 10.1002/mnfr.201801177. [PMID: 30815965]
  • Paulina Piechowska, Renata Zawirska-Wojtasiak, Sylwia Mildner-Szkudlarz. Bioactive β-Carbolines in Food: A Review. Nutrients. 2019 Apr; 11(4):. doi: 10.3390/nu11040814. [PMID: 30978920]
  • Ram B Jain. Concentrations of selected heterocyclic aromatic amines among US population aged ≥ 6 years: data from NHANES 2013-2014. Environmental science and pollution research international. 2018 Jul; 25(20):19859-19874. doi: 10.1007/s11356-018-2210-0. [PMID: 29737487]
  • Haroon Khan, Seema Patel, Mohammad A Kamal. Pharmacological and Toxicological Profile of Harmane-β-Carboline Alkaloid: Friend or Foe. Current drug metabolism. 2017; 18(9):853-857. doi: 10.2174/1389200218666170607100947. [PMID: 28595532]
  • Shuping Li, Liang Teng, Wei Liu, Xuemei Cheng, Bo Jiang, Zhengtao Wang, Chang-Hong Wang. Pharmacokinetic study of harmane and its 10 metabolites in rat after intravenous and oral administration by UPLC-ESI-MS/MS. Pharmaceutical biology. 2016 Sep; 54(9):1768-81. doi: 10.3109/13880209.2015.1127978. [PMID: 26730489]
  • Tomás Herraiz, Juan Galisteo. Naturally-occurring tetrahydro-β-carboline alkaloids derived from tryptophan are oxidized to bioactive β-carboline alkaloids by heme peroxidases. Biochemical and biophysical research communications. 2014 Aug; 451(1):42-7. doi: 10.1016/j.bbrc.2014.07.047. [PMID: 25035927]
  • Sudhakar Manda, Shabana I Khan, Surendra K Jain, Shabber Mohammed, Babu L Tekwani, Ikhlas A Khan, Ram A Vishwakarma, Sandip B Bharate. Synthesis, antileishmanial and antitrypanosomal activities of N-substituted tetrahydro-β-carbolines. Bioorganic & medicinal chemistry letters. 2014 Aug; 24(15):3247-50. doi: 10.1016/j.bmcl.2014.06.030. [PMID: 24980054]
  • Shuping Li, Wei Liu, Liang Teng, Xuemei Cheng, Zhengtao Wang, Changhong Wang. Metabolites identification of harmane in vitro/in vivo in rats by ultra-performance liquid chromatography combined with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis. 2014 Apr; 92(?):53-62. doi: 10.1016/j.jpba.2014.01.003. [PMID: 24486683]
  • Celesztina Domonkos, Ilona Fitos, Júlia Visy, Ferenc Zsila. Fatty acid modulated human serum albumin binding of the β-carboline alkaloids norharmane and harmane. Molecular pharmaceutics. 2013 Dec; 10(12):4706-16. doi: 10.1021/mp400531n. [PMID: 24171410]
  • Karen L Smith, Gemma K Ford, David S Jessop, David P Finn. Behavioural, neurochemical and neuroendocrine effects of the endogenous β-carboline harmane in fear-conditioned rats. Journal of psychopharmacology (Oxford, England). 2013 Feb; 27(2):162-70. doi: 10.1177/0269881112460108. [PMID: 23015542]
  • Mohammad Nasehi, Morteza Piri, Mojgan Abdollahian, Mohammad Reza Zarrindast. Involvement of nitrergic system of CA1in harmane induced learning and memory deficits. Physiology & behavior. 2013 Jan; 109(?):23-32. doi: 10.1016/j.physbeh.2012.10.006. [PMID: 23103833]
  • G- B Zhang, B Zhang, X- X Zhang, F- H Bing. Homonojirimycin, an alkaloid from dayflower inhibits the growth of influenza A virus in vitro. Acta virologica. 2013; 57(1):85-6. doi: 10.4149/av_2013_01_85. [PMID: 23530829]
  • Arkadiusz Szterk, Marek Roszko, Krystian Małek, Marcin Kurek, Monika Zbieć, Bożena Waszkiewicz-Robak. Profiles and concentrations of heterocyclic aromatic amines formed in beef during various heat treatments depend on the time of ripening and muscle type. Meat science. 2012 Dec; 92(4):587-95. doi: 10.1016/j.meatsci.2012.06.004. [PMID: 22762996]
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  • Bharathi Avula, Yan-Hong Wang, Chidananda Swamy Rumalla, Troy J Smillie, Ikhlas A Khan. Simultaneous determination of alkaloids and flavonoids from aerial parts of Passiflora species and dietary supplements using UPLC-UV-MS and HPTLC. Natural product communications. 2012 Sep; 7(9):1177-80. doi: . [PMID: 23074901]
  • Mohammad Nasehi, Shahrbano Sharifi, Mohammad Reza Zarrindast. Involvement of the cholinergic system of CA1 on harmane-induced amnesia in the step-down passive avoidance test. Journal of psychopharmacology (Oxford, England). 2012 Aug; 26(8):1151-61. doi: 10.1177/0269881111421972. [PMID: 21965190]
  • Bijan Kumar Paul, Nikhil Guchhait. Differential interactions of a biological photosensitizer with liposome membranes having varying surface charges. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology. 2012 Apr; 11(4):661-73. doi: 10.1039/c2pp05346b. [PMID: 22266915]
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  • Bijan Kumar Paul, Nikhil Guchhait. Modulation of prototropic activity and rotational relaxation dynamics of a cationic biological photosensitizer within the motionally constrained bio-environment of a protein. The journal of physical chemistry. B. 2011 Sep; 115(34):10322-34. doi: 10.1021/jp2015275. [PMID: 21790166]
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