Harmalol (BioDeep_00000006198)

 

Secondary id: BioDeep_00000278288

human metabolite Endogenous natural product


代谢物信息卡片


1-Methyl-4,9-dihydro-3H-beta-carbolin-7-ol hydrochloride

化学式: C12H12N2O (200.095)
中文名称: 去甲骆驼蓬碱
谱图信息: 最多检出来源 Viridiplantae(plant) 10.24%

分子结构信息

SMILES: CC1=c2[nH]c3c(c2CCN1)C=CC(=O)C=3
InChI: InChI=1S/C12H12N2O/c1-7-12-10(4-5-13-7)9-3-2-8(15)6-11(9)14-12/h2-3,6,14-15H,4-5H2,1H3

描述信息

Harmalol is found in fruits. Harmalol is an alkaloid from Passiflora incarnata (maypops). Harmaline is a reversible inhibitor of MAO-A (RIMA). Harmine is a reversible inhibitor of MAO-A (RIMA). It is important to note that unlike synthetic pharmaceutical MAOIs such as phenelzine, harmine is reversible and selective meaning it does not have nearly as high a risk for the "cheese syndrome" caused by consuming tyramine-containing foods, which is a risk associated with monoamine oxidase A inhibitors, but not monoamine oxidase B inhibitors. Several alkaloids that function as monoamine oxidase inhibitors (MAOIs) are found in the seeds of Peganum harmala (also known as Harmal or Syrian Rue), including harmine, harmaline, and harmalol, which are members of a group of substances with a similar chemical structure collectively known as harmala alkaloids. These alkaloids are of interest for their use in Amazonian shamanism, where they are derived from other plants. The harmala alkaloid harmine which was once known as Telepathine and Banisterine is a naturally occurring beta-carboline alkaloid that is structurally related to harmaline, and also found in the vine Banisteriopsis caapi. Tetrahydroharmine is also found in B. caapi, but not P. harmala. Dr. Alexander Shulgin has suggesed that harmaline may be a breakdown product of harmine. Harmine and harmaline are reversible MAOIs of the MAO-A isoform of the enzyme, and can stimulate the central nervous system by inhibiting the metabolism of monoamine compounds such as serotonin and norepinephrine. The harmala alkaloids occur in Peganum harmala in concentrations of roughly 3\\%, though tests have documented anywhere from 2-7\\%, as natural sources tend to vary widely in chemical makeup. Harmala alkaloids are also found in the Banisteriopsis caapi vine, the key plant ingredient in the sacramental beverage Ayahuasca, in concentrations that range between 0.31-8.43\\% for harmine, 0.03-0.83\\% for harmaline and 0.05-2.94\\% for tetrahydroharmine. Other psychoactive plants are often added to Ayahuasca to achieve visionary states of consciousness; for example leaves from Psychotria viridis, which is a source of dimethyltryptamine (DMT). The harmala alkaloids serve to potentiate these brewed compounds by preventing their breakdown in the digestive tract. The harmala alkaloids are not especially psychoactive on their own, even at high dosages, when vomiting and diarrhea become the main effect
Alkaloid from Passiflora incarnata (maypops)

同义名列表

20 个代谢物同义名

1-Methyl-4,9-dihydro-3H-beta-carbolin-7-ol hydrochloride; 4,9-dihydro-1-Methyl-3H-pyrido[3,4-b]indol-7-ol, 9ci; 4,9-dihydro-1-Methyl-3H-pyrido(3,4-b)indol-7-ol; 3,4-dihydro-1-Methyl-2H-pyrido[3,4-b]indol-7-ol; 4,9-dihydro-1-Methyl-3H-pyrido[3,4-b]indol-7-ol; 3,4-Dihydro-7-hydroxy-1-methyl-beta-carboline; 3,4-dihydro-7-Hydroxy-1-methyl-b-carboline; 1-Methyl-4,9-dihydro-3H-beta-carbolin-7-ol; 1-methyl-3H,4H,9H-pyrido[3,4-b]indol-7-ol; 1-Methyl-4,9-dihydro-3H-b-carbolin-7-ol; 1-Methyl-4,9-dihydro-3H-β-carbolin-7-ol; harmalol hydrochloride, dihydrate; harmalol lactate, dihydrate; harmalol dihydrochloride; Harmalol hydrochloride; harmalol trihydrate; Harmidol; Harmolol; harmalol; Harmalol



数据库引用编号

20 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(1)

代谢反应

1 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

64 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 14 AHR, ARNT, CASP3, CASP8, CASP9, CAT, CYP1A1, CYP2D6, CYP3A4, HELB, MAPK14, MITF, TYR, TYRP1
Peripheral membrane protein 3 ACHE, CYP1A1, CYP1B1
Endosome membrane 1 TYRP1
Endoplasmic reticulum membrane 5 CYP1A1, CYP1B1, CYP2D6, CYP3A4, HSP90B1
Nucleus 11 ACHE, AHR, ARNT, CASP3, CASP8, CASP9, FASLG, HELB, HSP90B1, MAPK14, MITF
cytosol 9 AHR, CASP3, CASP8, CASP9, CAT, HELB, HSP90B1, MAPK14, MITF
nuclear body 2 ARNT, HELB
nucleoplasm 7 AHR, ARNT, CASP3, CASP8, HELB, MAPK14, MITF
RNA polymerase II transcription regulator complex 1 ARNT
Cell membrane 2 ACHE, FASLG
lamellipodium 1 CASP8
Synapse 1 ACHE
cell surface 1 ACHE
glutamatergic synapse 2 CASP3, MAPK14
Golgi apparatus 1 ACHE
lysosomal membrane 1 MITF
mitochondrial inner membrane 1 CYP1A1
neuromuscular junction 1 ACHE
neuronal cell body 1 CASP3
smooth endoplasmic reticulum 1 HSP90B1
Lysosome 1 TYR
plasma membrane 4 ACHE, BCHE, F2, FASLG
Membrane 7 ACHE, CAT, CYP1B1, CYP2D6, CYP3A4, FASLG, HSP90B1
caveola 1 FASLG
extracellular exosome 4 CAT, F2, FASLG, HSP90B1
Lysosome membrane 1 MITF
endoplasmic reticulum 2 CYP2D6, HSP90B1
extracellular space 4 ACHE, BCHE, F2, FASLG
lysosomal lumen 1 FASLG
perinuclear region of cytoplasm 4 ACHE, FASLG, HSP90B1, TYR
mitochondrion 8 CASP8, CASP9, CAT, CYP1A1, CYP1B1, CYP2D6, HELB, MAPK14
protein-containing complex 6 AHR, CASP8, CASP9, CAT, HSP90B1, MITF
intracellular membrane-bounded organelle 6 CAT, CYP1A1, CYP1B1, CYP2D6, CYP3A4, TYR
Microsome membrane 4 CYP1A1, CYP1B1, CYP2D6, CYP3A4
postsynaptic density 1 CASP3
Single-pass type I membrane protein 2 TYR, TYRP1
Secreted 4 ACHE, BCHE, F2, FASLG
extracellular region 7 ACHE, BCHE, CAT, F2, FASLG, HSP90B1, MAPK14
Single-pass membrane protein 1 CYP2D6
mitochondrial outer membrane 1 CASP8
mitochondrial matrix 1 CAT
Extracellular side 1 ACHE
Cytoplasmic vesicle lumen 1 FASLG
transcription regulator complex 2 AHR, ARNT
external side of plasma membrane 1 FASLG
Melanosome membrane 2 TYR, TYRP1
midbody 1 HSP90B1
Golgi-associated vesicle 1 TYR
Single-pass type II membrane protein 1 FASLG
Cell projection, lamellipodium 1 CASP8
Mitochondrion inner membrane 1 CYP1A1
focal adhesion 2 CAT, HSP90B1
Peroxisome 1 CAT
basement membrane 1 ACHE
intracellular vesicle 1 TYRP1
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 2 F2, HSP90B1
nuclear speck 1 MAPK14
chromatin 3 AHR, ARNT, MITF
Chromosome 1 HELB
cytoskeleton 1 CASP8
spindle pole 1 MAPK14
blood microparticle 2 BCHE, F2
Lipid-anchor, GPI-anchor 1 ACHE
site of double-strand break 1 HELB
aryl hydrocarbon receptor complex 2 AHR, ARNT
Melanosome 3 HSP90B1, TYR, TYRP1
cell body 1 CASP8
side of membrane 1 ACHE
sperm plasma membrane 1 HSP90B1
ficolin-1-rich granule lumen 2 CAT, MAPK14
secretory granule lumen 2 CAT, MAPK14
Golgi lumen 1 F2
endoplasmic reticulum lumen 3 BCHE, F2, HSP90B1
Lysosome lumen 1 FASLG
nuclear envelope lumen 1 BCHE
apoptosome 1 CASP9
clathrin-coated endocytic vesicle membrane 1 TYRP1
Sarcoplasmic reticulum lumen 1 HSP90B1
synaptic cleft 1 ACHE
CD95 death-inducing signaling complex 1 CASP8
death-inducing signaling complex 2 CASP3, CASP8
ripoptosome 1 CASP8
endocytic vesicle lumen 1 HSP90B1
catalase complex 1 CAT
endoplasmic reticulum chaperone complex 1 HSP90B1
[Isoform H]: Cell membrane 1 ACHE
nuclear aryl hydrocarbon receptor complex 2 AHR, ARNT
cytosolic aryl hydrocarbon receptor complex 1 AHR
[Tumor necrosis factor ligand superfamily member 6, soluble form]: Secreted 1 FASLG
[FasL intracellular domain]: Nucleus 1 FASLG
caspase complex 1 CASP9


文献列表

  • Silvia Biggi, Michael Pancher, Claudia Stincardini, Silvia Luotti, Tania Massignan, Andrea Dalle Vedove, Andrea Astolfi, Pamela Gatto, Graziano Lolli, Maria Letizia Barreca, Valentina Bonetto, Valentina Adami, Emiliano Biasini. Identification of compounds inhibiting prion replication and toxicity by removing PrPC from the cell surface. Journal of neurochemistry. 2020 01; 152(1):136-150. doi: 10.1111/jnc.14805. [PMID: 31264722]
  • Sarita Sarkar, Kakali Bhadra. Therapeutic Role of Harmalol Targeting Nucleic Acids: Biophysical Perspective and in vitro Cytotoxicity. Mini reviews in medicinal chemistry. 2018; 18(19):1624-1639. doi: 10.2174/1389557518666171211164830. [PMID: 29231137]
  • Marcos Tascón, Fernando Benavente, Nora M Vizioli, Leonardo G Gagliardi. A rapid and simple method for the determination of psychoactive alkaloids by CE-UV: application to Peganum Harmala seed infusions. Drug testing and analysis. 2017 Apr; 9(4):596-602. doi: 10.1002/dta.1989. [PMID: 27377797]
  • Lei Zhang, Liang Teng, Can Gong, Wei Liu, Xuemei Cheng, Shenghua Gu, Zhongping Deng, Zhengtao Wang, Changhong Wang. Simultaneous determination of harmine, harmaline and their metabolites harmol and harmalol in beagle dog plasma by UPLC-ESI-MS/MS and its application to a pharmacokinetic study. Journal of pharmaceutical and biomedical analysis. 2013 Nov; 85(?):162-8. doi: 10.1016/j.jpba.2013.07.019. [PMID: 23948761]
  • Bahram Hemmateenejad, Mojtaba Shamsipur, Fayezeh Samari, Taghi Khayamian, Malihe Ebrahimi, Zahra Rezaei. Combined fluorescence spectroscopy and molecular modeling studies on the interaction between harmalol and human serum albumin. Journal of pharmaceutical and biomedical analysis. 2012 Aug; 67-68(?):201-8. doi: 10.1016/j.jpba.2012.04.012. [PMID: 22560122]
  • Sun Young Park, Young Hun Kim, Young Hee Kim, Geuntae Park, Sang-Joon Lee. Beta-carboline alkaloids harmaline and harmalol induce melanogenesis through p38 mitogen-activated protein kinase in B16F10 mouse melanoma cells. BMB reports. 2010 Dec; 43(12):824-9. doi: 10.5483/bmbrep.2010.43.12.824. [PMID: 21189160]
  • Akihisa Abe, Hiroyuki Yamada. Harmol induces apoptosis by caspase-8 activation independently of Fas/Fas ligand interaction in human lung carcinoma H596 cells. Anti-cancer drugs. 2009 Jun; 20(5):373-81. doi: 10.1097/cad.0b013e32832a2dd9. [PMID: 19318910]
  • A Movafeghi, M Abedini, F Fathiazad, M Aliasgharpour, Y Omidi. Floral nectar composition of Peganum harmala L. Natural product research. 2009; 23(3):301-8. doi: 10.1080/14786410802076291. [PMID: 19235031]
  • Najma Arshad, Karin Zitterl-Eglseer, Shahida Hasnain, Michael Hess. Effect of Peganum harmala or its beta-carboline alkaloids on certain antibiotic resistant strains of bacteria and protozoa from poultry. Phytotherapy research : PTR. 2008 Nov; 22(11):1533-8. doi: 10.1002/ptr.2528. [PMID: 18814210]
  • C S Lee, E S Han, Y Y Jang, J H Han, H W Ha, D E Kim. Protective effect of harmalol and harmaline on MPTP neurotoxicity in the mouse and dopamine-induced damage of brain mitochondria and PC12 cells. Journal of neurochemistry. 2000 Aug; 75(2):521-31. doi: 10.1046/j.1471-4159.2000.0750521.x. [PMID: 10899927]
  • R S Zand, D J Jenkins, E P Diamandis. Steroid hormone activity of flavonoids and related compounds. Breast cancer research and treatment. 2000 Jul; 62(1):35-49. doi: 10.1023/a:1006422302173. [PMID: 10989984]
  • S Y Tse, I T Mak, B F Dickens. Antioxidative properties of harmane and beta-carboline alkaloids. Biochemical pharmacology. 1991 Jul; 42(3):459-64. doi: 10.1016/0006-2952(91)90305-o. [PMID: 1859459]