Harmol (BioDeep_00000230791)

 

Secondary id: BioDeep_00000019007, BioDeep_00001891224

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


1-Methyl-9H-pyrido[3,4-b]indol-7-ol Monohydrochloride Dihydrate

化学式: C12H10N2O (198.079309)
中文名称: 哈尔酚
谱图信息: 最多检出来源 Viridiplantae(plant) 0.56%

分子结构信息

SMILES: CC1=C2C(=C3C=CC(=O)C=C3N2)C=CN1
InChI: InChI=1S/C12H10N2O/c1-7-12-10(4-5-13-7)9-3-2-8(15)6-11(9)14-12/h2-6,13-14H,1H3

描述信息

Harmol is a 9H-beta-carboline carrying a methyl substituent at C-1 and a hydroxy group at C-7; major microspecies at pH 7.3. It has a role as an antifungal agent, an apoptosis inducer and an autophagy inducer. It is a harmala alkaloid and an indole alkaloid. It is functionally related to a beta-carboline.
Harmol is a natural product found in Fontinalis squamosa, Passiflora foetida, and other organisms with data available.
Annotation level-1
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.454
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.443
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.442
Harmol categorized as a β-carboline alkaloid. Harmol is a potent MAO inhibitor used as an analytical reference standard[1].
Harmol categorized as a β-carboline alkaloid. Harmol is a potent MAO inhibitor used as an analytical reference standard[1].

同义名列表

47 个代谢物同义名

1-Methyl-9H-pyrido[3,4-b]indol-7-ol Monohydrochloride Dihydrate; 1-Methyl-2,9-dihydro-7H-pyrido[3,4-b]indol-7-one; 9H-Pyrido(3,4-b)indol-7-ol, 1-methyl- (8CI)(9CI); 1-methyl-2,9-dihydropyrido[3,4-b]indol-7-one; 7-Hydroxy-1-methyl-9H-pyrido[3,4-b]indole; 1-Methyl-9H-beta-carbolin-7-ol (harmalol); 1-methyl-2,9-dihydro-beta-carbolin-7-one; 1-Methyl-9H-pyrido[3,4-b]indol-7-ol, 9CI; 1-methyl-9~{H}-pyrido[3,4-b]indol-7-ol; 9H-Pyrido[3,4-b]indol-7-ol, 1-methyl-; .beta.-Carboline, 7-hydroxy-1-methyl-; 9H-Pyrido(3,4-b)indol-7-ol, 1-methyl-; 1-Methyl-9H-pyrido(3,4-b)indol-7-ol; 1-methyl-9H-pyrido[3,4-b]indol-7-ol; 7-hydroxyl-1-methyl-beta-carboline; beta 7-Hydroxy-1-methyl--Carboline; 1-methyl-7-hydroxy-beta-carboline; 1-Methyl-9H-beta-carbolin-7-ol #; 1-Methyl-9H-beta-carbolin-7-ol; 1-Methyl-9H-?-carbolin-7-ol; 1-methylbeta-carbolin-7-ol; harmol hydrochloride; harmol hydrobromride; Methylpyridoindolol; Prestwick2_000612; Prestwick3_000612; Prestwick1_000612; Prestwick0_000612; Spectrum3_001531; Spectrum2_000504; Spectrum4_000214; Spectrum5_000853; UNII-7PQ075MCA6; NCIOpen2_000349; 7-Hydroxyharman; DivK1c_006548; BPBio1_000600; KBio3_002442; KBio1_001492; NCI60_013489; KBio2_005955; KBio2_000819; KBio2_003387; 7PQ075MCA6; A1-00784; Harmol; HFI



数据库引用编号

46 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

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)

103 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

  • 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]
  • 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]
  • Akihisa Abe, Hiroko Kokuba. Harmol induces autophagy and subsequent apoptosis in U251MG human glioma cells through the downregulation of survivin. Oncology reports. 2013 Apr; 29(4):1333-42. doi: 10.3892/or.2013.2242. [PMID: 23338618]
  • 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]
  • 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]
  • Jordi Riba, Ethan H McIlhenny, Marta Valle, José Carlos Bouso, Steven A Barker. Metabolism and disposition of N,N-dimethyltryptamine and harmala alkaloids after oral administration of ayahuasca. Drug testing and analysis. 2012 Jul; 4(7-8):610-6. doi: 10.1002/dta.1344. [PMID: 22514127]
  • Gregory J Anger, Alex M Cressman, Micheline Piquette-Miller. Expression of ABC Efflux transporters in placenta from women with insulin-managed diabetes. PloS one. 2012; 7(4):e35027. doi: 10.1371/journal.pone.0035027. [PMID: 22558111]
  • Ting Zhao, Yu-qi He, Jun Wang, Ke-min Ding, Chang-hong Wang, Zheng-tao Wang. Inhibition of human cytochrome P450 enzymes 3A4 and 2D6 by β-carboline alkaloids, harmine derivatives. Phytotherapy research : PTR. 2011 Nov; 25(11):1671-7. doi: 10.1002/ptr.3458. [PMID: 21433154]
  • Hironori Tsuchiya. Comparative Effects of α-, β-, and γ-Carbolines on Platelet Aggregation and Lipid Membranes. Journal of toxicology. 2011; 2011(?):151596. doi: 10.1155/2011/151596. [PMID: 21876689]
  • Nahida Tabassum, Feroz Ahmad. Role of natural herbs in the treatment of hypertension. Pharmacognosy reviews. 2011 Jan; 5(9):30-40. doi: 10.4103/0973-7847.79097. [PMID: 22096316]
  • Akihisa Abe, Hiroyuki Yamada, Shota Moriya, Keisuke Miyazawa. The β-carboline alkaloid harmol induces cell death via autophagy but not apoptosis in human non-small cell lung cancer A549 cells. Biological & pharmaceutical bulletin. 2011; 34(8):1264-72. doi: 10.1248/bpb.34.1264. [PMID: 21804216]
  • 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]
  • Gislaine Z Réus, Roberto B Stringari, Bruna de Souza, Fabrícia Petronilho, Felipe Dal-Pizzol, Jaime E Hallak, Antônio W Zuardi, José A Crippa, João Quevedo. Harmine and imipramine promote antioxidant activities in prefrontal cortex and hippocampus. Oxidative medicine and cellular longevity. 2010 Sep; 3(5):325-31. doi: 10.4161/oxim.3.5.13109. [PMID: 21150338]
  • T Herraiz, D González, C Ancín-Azpilicueta, V J Arán, H Guillén. beta-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO). Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2010 Mar; 48(3):839-45. doi: 10.1016/j.fct.2009.12.019. [PMID: 20036304]
  • Xi-yuan Zheng, Zi-jia Zhang, Gui-xin Chou, Tao Wu, Xue-mei Cheng, Chang-hong Wang, Zheng-tao Wang. Acetylcholinesterase inhibitive activity-guided isolation of two new alkaloids from seeds of Peganum nigellastrum Bunge by an in vitro TLC- bioautographic assay. Archives of pharmacal research. 2009 Sep; 32(9):1245-51. doi: 10.1007/s12272-009-1910-x. [PMID: 19784581]
  • 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]
  • Ji-Hyun Im, Yong-Ri Jin, Jung-Jin Lee, Ji-Yeon Yu, Xiang-Hua Han, Se-Hyuk Im, Jin Tae Hong, Hwan-Soo Yoo, Myoung-Yun Pyo, Yeo-Pyo Yun. Antiplatelet activity of beta-carboline alkaloids from Perganum harmala: a possible mechanism through inhibiting PLCgamma2 phosphorylation. Vascular pharmacology. 2009 May; 50(5-6):147-52. doi: 10.1016/j.vph.2008.11.008. [PMID: 19073282]
  • 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]
  • R G Santos, J Landeira-Fernandez, R J Strassman, V Motta, A P M Cruz. Effects of ayahuasca on psychometric measures of anxiety, panic-like and hopelessness in Santo Daime members. Journal of ethnopharmacology. 2007 Jul; 112(3):507-13. doi: 10.1016/j.jep.2007.04.012. [PMID: 17532158]
  • Sabira Begum, Syed Imran Hassan, Bina S Siddiqui. Synthesis and antimycobacterial activity of some beta-carboline alkaloids. Natural product research. 2004 Aug; 18(4):341-7. doi: 10.1080/14786410310001622040. [PMID: 15214487]
  • Kian Hong Ng, Beng Gek Lim, Kim Ping Wong. Sulfate conjugating and transport functions of MDCK distal tubular cells. Kidney international. 2003 Mar; 63(3):976-86. doi: 10.1046/j.1523-1755.2003.00818.x. [PMID: 12631078]
  • Mercedes Yritia, Jordi Riba, Jordi Ortuño, Ariel Ramirez, Araceli Castillo, Yolanda Alfaro, Rafael de la Torre, Manel J Barbanoj. Determination of N,N-dimethyltryptamine and beta-carboline alkaloids in human plasma following oral administration of Ayahuasca. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2002 Nov; 779(2):271-81. doi: 10.1016/s1570-0232(02)00397-5. [PMID: 12361741]
  • J W Boles, C D Klaassen. Effects of molybdate on the sulfation of harmol and alpha-naphthol. Toxicology. 1998 May; 127(1-3):121-7. doi: 10.1016/s0300-483x(98)00029-8. [PMID: 9699799]
  • D J Morgan, A Guttmann, R G Watson, H Ghabrial, S L Elliott, R A Smallwood. Effect of erythrocyte binding on elimination of harmol by the isolated perfused rat liver. Journal of pharmaceutical sciences. 1996 Jan; 85(1):40-4. doi: 10.1021/js950282e. [PMID: 8926581]
  • J Moncrieff. Extractionless determination of diclofenac sodium in serum using reversed-phase high-performance liquid chromatography with fluorimetric detection. Journal of chromatography. 1992 May; 577(1):185-9. doi: 10.1016/0378-4347(92)80618-z. [PMID: 1400740]
  • 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]
  • Z Gregus, C White, S Howell, C D Klaassen. Effect of glutathione depletion on sulfate activation and sulfate ester formation in rats. Biochemical pharmacology. 1988 Nov; 37(22):4307-12. doi: 10.1016/0006-2952(88)90611-9. [PMID: 3196355]
  • G J Mulder. Kinetics of sulfation in the rat in vivo and in the perfused rat liver. Federation proceedings. 1986 Jul; 45(8):2229-34. doi: NULL. [PMID: 3087784]
  • M H de Vries, G M Groothuis, G J Mulder, H Nguyen, D K Meijer. Secretion of the organic anion harmol sulfate from liver into blood. Evidence for a carrier-mediated mechanism. Biochemical pharmacology. 1985 Jun; 34(12):2129-35. doi: 10.1016/0006-2952(85)90406-x. [PMID: 4004931]
  • E J Glazenburg, I M Jekel-Halsema, A Baranczyk-Kuzma, K R Krijgsheld, G J Mulder. D-cysteine as a selective precursor for inorganic sulfate in the rat in vivo. Effect of D-cysteine on the sulfation of harmol. Biochemical pharmacology. 1984 Feb; 33(4):625-8. doi: 10.1016/0006-2952(84)90318-6. [PMID: 6704178]
  • J H Meerman, H M Sterenborg, G J Mulder. Use of pentachlorophenol as long-term inhibitor of sulfation of phenols and hydroxamic acids in the rat in vivo. Biochemical pharmacology. 1983 May; 32(10):1587-93. doi: 10.1016/0006-2952(83)90332-5. [PMID: 6860346]
  • K P Wong, T Yeo. Importance of extrahepatic sulphate conjugation. Biochemical pharmacology. 1982 Dec; 31(24):4001-3. doi: 10.1016/0006-2952(82)90647-5. [PMID: 6818973]
  • K R Krijgsheld, H J Koster, E Scholtens, G J Mulder. Cholestatic effect of harmol glucuronide in the rat. Prevention of harmol-induced cholestasis by increased formation of harmol sulfate. The Journal of pharmacology and experimental therapeutics. 1982 Jun; 221(3):731-4. doi: NULL. [PMID: 7086685]
  • H Koster, I Halsema, E Scholtens, J H Meerman, K S Pang, G J Mulder. Selective inhibition of sulfate conjugation in the rat: pharmacokinetics and characterization of the inhibitory effect of 2,6-dichloro-4-nitrophenol. Biochemical pharmacology. 1982 May; 31(10):1919-24. doi: 10.1016/0006-2952(82)90498-1. [PMID: 7104024]
  • G J Mulder, K Keulemans. Metabolism of inorganic sulphate in the isolated perfused rat liver. Effect of sulphate concentration on the rate of sulphation by phenol sulphotransferase. The Biochemical journal. 1978 Dec; 176(3):959-65. doi: 10.1042/bj1760959. [PMID: 747664]
  • G J Mulder, E Scholtens. The availability of inorganic sulphate in blood for sulphate conjugation of drugs in rat liver in vivo. (35S)Sulphate incorporation into harmol sulphate. The Biochemical journal. 1978 May; 172(2):247-51. doi: 10.1042/bj1720247. [PMID: 666743]
  • G J Mulder, B Bleeker. UDP glucuronyltransferase and phenolsulfotransferase from rat liver in vivo and in vitro--IV. Species differences in harmol conjugation and elimination in bile and urine in vivo. Biochemical pharmacology. 1975 Aug; 24(16):1481-4. doi: 10.1016/0006-2952(75)90022-2. [PMID: 811225]
  • G J Mulder, A H Pilon. UDP glucuronyltransferase and phenolsulfotransferase from rat liver in vivo and in vitro. III. The effect of phenolphthalein and its sulfate and glucuronide conjugate on conjugation and biliary excretion of harmol. Biochemical pharmacology. 1975 Feb; 24(4):517-21. doi: 10.1016/0006-2952(75)90138-0. [PMID: 803377]