Hydroquinidine (BioDeep_00000003597)

 

Secondary id: BioDeep_00000229964

natural product PANOMIX_OTCML-2023


代谢物信息卡片


NCGC00385753-01_C20H26N2O2_Cinchonan-9-ol, 10,11-dihydro-6-methoxy-, (9S)-

化学式: C20H26N2O2 (326.1994)
中文名称: 氢化奎尼定
谱图信息: 最多检出来源 Viridiplantae(plant) 8.05%

分子结构信息

SMILES: CCC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)OC)O
InChI: InChI=1S/C20H26N2O2/c1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18/h4-6,8,11,13-14,19-20,23H,3,7,9-10,12H2,1-2H3

描述信息

Same as: D08048
C - Cardiovascular system > C01 - Cardiac therapy > C01B - Antiarrhythmics, class i and iii > C01BA - Antiarrhythmics, class ia
D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D010276 - Parasympatholytics
D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.751
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.749
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.745
relative retention time with respect to 9-anthracene Carboxylic Acid is 0.742
Hydroquinidine (Dihydroquinidine) is a derivative of Quinidine (an antiarrhythmic agent). Hydroquinidine prolongs the QT interval and has antiarrhythmic efficacy[1][2][3].
Hydroquinidine (Dihydroquinidine) is a derivative of Quinidine (an antiarrhythmic agent). Hydroquinidine prolongs the QT interval and has antiarrhythmic efficacy[1][2][3].

同义名列表

6 个代谢物同义名

Hydroquinidine; NCGC00385753-01_C20H26N2O2_Cinchonan-9-ol, 10,11-dihydro-6-methoxy-, (9S)-; Dihydroquinidine; (+)-Hydroquinidine; Hydroconquinine; Hydroquinidine



数据库引用编号

86 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 14 ADRA1A, ANXA5, AXIN2, CDK1, CDK6, MCM2, PSMA1, PSMB5, PSMC2, PSME2, RRM2, YWHAB, YWHAH, YWHAQ
Peripheral membrane protein 1 ANXA5
Endoplasmic reticulum membrane 1 CDK1
Nucleus 13 ADRA1A, AXIN2, CDK1, CDK6, MCM2, MCM7, PSMA1, PSMB5, PSMC2, PSMD2, RRM2, YWHAB, YWHAQ
cytosol 16 ADRA1A, ANXA5, AXIN2, CDK1, CDK6, MCM2, MCM7, PSMA1, PSMB5, PSMC2, PSMD2, PSME2, RRM2, YWHAB, YWHAH, YWHAQ
centrosome 5 AXIN2, CDK1, CDK6, PSMA1, PSMB5
nucleoplasm 12 ADRA1A, CDK1, CDK6, MCM2, MCM7, PSMA1, PSMB5, PSMC2, PSMD2, PSME2, SCN5A, SCNN1G
Cell membrane 2 ADRA1A, SCN5A
Multi-pass membrane protein 4 ADRA1A, KCNA3, SCN5A, SCNN1G
Synapse 1 YWHAQ
cell junction 1 SCN5A
cell surface 1 SCN5A
glutamatergic synapse 1 KCNA3
presynaptic membrane 1 KCNA3
sarcolemma 2 ANXA5, SCN5A
Presynapse 1 YWHAH
plasma membrane 6 ADRA1A, AXIN2, KCNA3, SCN5A, SCNN1G, YWHAH
Membrane 11 ANXA5, CDK1, KCNA3, MCM2, MCM7, PSMC2, PSMD2, PSME2, SCN5A, YWHAB, YWHAQ
apical plasma membrane 1 SCNN1G
axon 1 KCNA3
caveola 2 ADRA1A, SCN5A
extracellular exosome 10 ANXA5, CDK1, PSMA1, PSMB5, PSMD2, PSME2, SCNN1G, YWHAB, YWHAH, YWHAQ
endoplasmic reticulum 1 SCN5A
perinuclear region of cytoplasm 3 KCNA3, SCN5A, YWHAB
intercalated disc 2 SCN5A, YWHAH
mitochondrion 2 CDK1, YWHAH
protein-containing complex 1 YWHAQ
intracellular membrane-bounded organelle 1 ADRA1A
extracellular region 3 ANXA5, PSMC2, PSMD2
mitochondrial matrix 1 CDK1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 2 CDK1, CDK6
Nucleus membrane 1 ADRA1A
nuclear membrane 1 ADRA1A
external side of plasma membrane 2 ANXA5, SCNN1G
T-tubule 1 SCN5A
Z disc 1 SCN5A
beta-catenin destruction complex 1 AXIN2
nucleolus 1 SCN5A
midbody 1 CDK1
P-body 1 PSMC2
postsynaptic membrane 1 KCNA3
Apical cell membrane 1 SCNN1G
Cytoplasm, perinuclear region 1 SCN5A
Membrane raft 1 KCNA3
focal adhesion 3 ANXA5, YWHAB, YWHAQ
collagen-containing extracellular matrix 1 ANXA5
lateral plasma membrane 1 SCN5A
ruffle 1 CDK6
Zymogen granule membrane 1 ANXA5
chromatin 2 MCM2, MCM7
mitotic spindle 1 CDK1
Chromosome 2 MCM2, MCM7
cytoplasmic ribonucleoprotein granule 1 PSMC2
chromosome, telomeric region 3 CDK1, MCM2, MCM7
proteasome core complex, beta-subunit complex 1 PSMB5
[Isoform 2]: Cell membrane 1 KCNA3
Membrane, caveola 1 ADRA1A
sodium channel complex 1 SCNN1G
Melanosome 1 YWHAB
Cell membrane, sarcolemma, T-tubule 1 SCN5A
voltage-gated potassium channel complex 1 KCNA3
ficolin-1-rich granule lumen 2 PSMC2, PSMD2
proteasome accessory complex 2 PSMC2, PSMD2
proteasome complex 5 PSMA1, PSMB5, PSMC2, PSMD2, PSME2
secretory granule lumen 2 PSMC2, PSMD2
proteasome regulatory particle 1 PSMD2
calyx of Held 1 KCNA3
proteasome core complex 2 PSMA1, PSMB5
proteasome core complex, alpha-subunit complex 1 PSMA1
vesicle membrane 1 ANXA5
spindle microtubule 1 CDK1
[Isoform 1]: Cell membrane 1 KCNA3
nuclear origin of replication recognition complex 1 MCM2
voltage-gated sodium channel complex 1 SCN5A
CMG complex 2 MCM2, MCM7
cyclin-dependent protein kinase holoenzyme complex 2 CDK1, CDK6
cyclin A1-CDK1 complex 1 CDK1
cyclin A2-CDK1 complex 1 CDK1
cyclin B1-CDK1 complex 1 CDK1
vacuolar membrane 1 YWHAB
endothelial microparticle 1 ANXA5
proteasome regulatory particle, base subcomplex 2 PSMC2, PSMD2
[Isoform 3]: Cytoplasm, perinuclear region 1 KCNA3
ribonucleoside-diphosphate reductase complex 1 RRM2
cyclin D1-CDK6 complex 1 CDK6
MCM complex 2 MCM2, MCM7
cyclin D3-CDK6 complex 1 CDK6
Vacuole membrane 1 YWHAB
proteasome activator complex 1 PSME2
cyclin D2-CDK6 complex 1 CDK6
cerebellar granule cell to Purkinje cell synapse 1 YWHAH
proteasome storage granule 1 PSMD2


文献列表

  • Zhiping Che, Jinming Yang, Di Sun, Yuee Tian, Shengming Liu, Xiaomin Lin, Jia Jiang, Genqiang Chen. Synthesis of Novel (9S)-Acyloxy Derivatives of Quinidine and Dihydroquinidine as Insecticidal Agents. Chemistry & biodiversity. 2020 Apr; 17(4):e1900696. doi: 10.1002/cbdv.201900696. [PMID: 32134169]
  • Dongsheng Xu, Qiqin Wang, Elena Sánchez-López, Zhengjin Jiang, María Luisa Marina. Preparation of an O-[2-(methacryloyloxy)-ethylcarbamoyl]-10,11-dihydroquinidine-silica hybrid monolithic column for the enantioseparation of amino acids by nano-liquid chromatography. Journal of chromatography. A. 2019 May; 1593(?):63-72. doi: 10.1016/j.chroma.2019.01.065. [PMID: 30712817]
  • Adele Murauer, Markus Ganzera. Quantitative determination of major alkaloids in Cinchona bark by Supercritical Fluid Chromatography. Journal of chromatography. A. 2018 Jun; 1554(?):117-122. doi: 10.1016/j.chroma.2018.04.038. [PMID: 29699870]
  • Huihui Wu, Qiqin Wang, Meng Ruan, Kun Peng, Peijie Zhu, Jacques Crommen, Hai Han, Zhengjin Jiang. Enantioseparation of N-derivatized amino acids by micro-liquid chromatography/laser induced fluorescence detection using quinidine-based monolithic columns. Journal of pharmaceutical and biomedical analysis. 2016 Mar; 121(?):244-252. doi: 10.1016/j.jpba.2015.12.011. [PMID: 26732881]
  • Demetri Orphanos, Crist N Filer. Ethyl-³H analogues of plant natural products: Biologically active proxy radioligands via vinyl group tritiation. Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine. 2016 Jan; 107(?):203-205. doi: 10.1016/j.apradiso.2015.10.013. [PMID: 26520478]
  • Philippe Rasoanaivo, Colin W Wright, Merlin L Willcox, Ben Gilbert. Whole plant extracts versus single compounds for the treatment of malaria: synergy and positive interactions. Malaria journal. 2011 Mar; 10 Suppl 1(?):S4. doi: 10.1186/1475-2875-10-s1-s4. [PMID: 21411015]
  • Xiaoyi Wei, Gengliang Yang, Li Qi, Yi Chen. Determination of nicardipine and amlodipine in human plasma using on-line solid-phase extraction with a monolithic weak cation-exchange column. Talanta. 2009 Jan; 77(3):1197-202. doi: 10.1016/j.talanta.2008.08.034. [PMID: 19064112]
  • David C Warhurst, John C Craig, Ipemida S Adagu, David J Meyer, Sylvia Y Lee. The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids. Malaria journal. 2003 Sep; 2(?):26. doi: 10.1186/1475-2875-2-26. [PMID: 14505493]
  • C K Mannesse, T J M van der Cammen. [Adverse drug reactions in three older patients, even without changes in medication]. Nederlands tijdschrift voor geneeskunde. 2003 Mar; 147(13):585-7. doi: NULL. [PMID: 12701389]
  • Veronica Harvey, Hamed Benghuzzi, Michell Tucci, Aaron Puckett, Zelma Cason. Proliferation and morphological transformation of RMK cells exposed to hydroquinine containing ionomers. Biomedical sciences instrumentation. 2002; 38(?):185-90. doi: NULL. [PMID: 12085599]
  • H Roche, G Bogé. In vivo effects of phenolic compounds on blood parameters of a marine fish (Dicentrarchus labrax). Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2000 Mar; 125(3):345-53. doi: 10.1016/s0742-8413(99)00119-x. [PMID: 11790355]
  • E Ludwig, J Schmid, K Beschke, T Ebner. Activation of human cytochrome P-450 3A4-catalyzed meloxicam 5'-methylhydroxylation by quinidine and hydroquinidine in vitro. The Journal of pharmacology and experimental therapeutics. 1999 Jul; 290(1):1-8. doi: . [PMID: 10381752]
  • I Meineke, S Rohde, U Gundert-Remy. An inexpensive and sensitive method for the determination of quinidine in plasma by high-performance liquid chromatography with ultraviolet detection. Therapeutic drug monitoring. 1995 Feb; 17(1):75-8. doi: 10.1097/00007691-199502000-00012. [PMID: 7725381]
  • F Nielsen, K K Nielsen, K Brøsen. Determination of quinidine, dihydroquinidine, (3S)-3-hydroxyquinidine and quinidine N-oxide in plasma and urine by high-performance liquid chromatography. Journal of chromatography. B, Biomedical applications. 1994 Oct; 660(1):103-10. doi: 10.1016/0378-4347(94)00259-2. [PMID: 7858702]
  • S Lévy, C Moyal, E Dolla, R Cointe, P Bru, P Lauribe, F Paganelli, P Chanu, R Gérard. [Comparison of the efficacy of 2 delayed-action preparations of hydroquinidine and quinidine in the prevention of pacing induced ventricular tachycardia]. Archives des maladies du coeur et des vaisseaux. 1993 Sep; 86(9):1359-63. doi: . [PMID: 8129554]
  • G L Hoyer, D C Clawson, L A Brookshier, P E Nolan, F I Marcus. High-performance liquid chromatographic method for the quantitation of quinidine and selected quinidine metabolites. Journal of chromatography. 1991 Dec; 572(1-2):159-69. doi: 10.1016/0378-4347(91)80480-z. [PMID: 1818051]
  • F Chézalviel, J Weissenburger, O Ertzbischoff, J M Poirier, X Harlé, J M Davy, M Biour, G Cheymol. Comparison of the cardiac electrophysiological effects of flecainide and hydroquinidine in anesthetized dog: concentration-response relationship. Journal of cardiovascular pharmacology. 1990 Jan; 15(1):50-6. doi: 10.1097/00005344-199001000-00008. [PMID: 1688982]
  • K M Kavanagh, D G Wyse, L B Mitchell, T Gilhooly, A M Gillis, H J Duff. Contribution of quinidine metabolites to electrophysiologic responses in human subjects. Clinical pharmacology and therapeutics. 1989 Sep; 46(3):352-8. doi: 10.1038/clpt.1989.150. [PMID: 2776394]
  • M Chimienti, M B Regazzi, M T La Rovere, J A Salerno, M Previtali, V Montericcio, R Rondanelli, C Montemartini. Comparison of the effectiveness of dihydroquinidine and quinidine on ventricular ectopy after acute and chronic administration. Cardiovascular drugs and therapy. 1988 Dec; 2(5):679-86. doi: 10.1007/bf00054209. [PMID: 2484920]
  • K A Thompson, J J Murray, I A Blair, R L Woosley, D M Roden. Plasma concentrations of quinidine, its major metabolites, and dihydroquinidine in patients with torsades de pointes. Clinical pharmacology and therapeutics. 1988 Jun; 43(6):636-42. doi: 10.1038/clpt.1988.88. [PMID: 3378385]
  • M Ferriere, J P Selles, G Panis, R Panis, I Lacheretz, J Seguin, H Jaber, J P Daures, C Gorget. Intramyocardial distribution of hydroquinidine in the dog. Cardiovascular research. 1988 May; 22(5):372-4. doi: 10.1093/cvr/22.5.372. [PMID: 3191521]
  • M P Quaglio, A M Bellini. [Simultaneous determination of quinidine and hydroquinidine in in the presence of benzodiazepine in human plasma]. Il Farmaco; edizione pratica. 1988 Feb; 43(2):47-55. doi: NULL. [PMID: 3396688]
  • K A Thompson, I A Blair, R L Woosley, D M Roden. Comparative in vitro electrophysiology of quinidine, its major metabolites and dihydroquinidine. The Journal of pharmacology and experimental therapeutics. 1987 Apr; 241(1):84-90. doi: . [PMID: 3572799]
  • P Jaillon, J M Poirier, B Lecocq, C Jarreau, M Pays, M O Richard, G Cheymol. Pharmacokinetics of hydroxy-3(S)-dihydroquinidine in healthy volunteers after intravenous and oral administration. European journal of drug metabolism and pharmacokinetics. 1986 Jul; 11(3):233-8. doi: 10.1007/bf03189851. [PMID: 3816879]
  • M Chimienti, C Panciroli, J A Salerno, M Regazzi-Bonora, M Previtali, D Cristiani, R Rondanelli, P Bobba. Dihydroquinidine versus disopyramide: efficacy in patients with chronic stable ventricular ectopy. Clinical cardiology. 1984 Oct; 7(10):538-46. doi: 10.1002/clc.4960071005. [PMID: 6386253]
  • R Camsonne, M A Moulin, F Albessard, M Perault. A simple fluorescence high-performance liquid chromatographic assay for dihydroquinidine in serum. Therapeutic drug monitoring. 1984; 6(4):471-3. doi: 10.1097/00007691-198412000-00017. [PMID: 6515710]
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  • P A Reece, M Peikert. Simple and selective high-performance liquid chromatographic method for estimating plasma quinidine levels. Journal of chromatography. 1980 Feb; 181(2):207-17. doi: 10.1016/s0378-4347(00)81606-0. [PMID: 7372754]
  • C G AGNOLI. [The antagonistic effect acetylcholine on block of terminal conduction in the rabbit serum induced by hydroquinidine]. Bollettino della Societa italiana di biologia sperimentale. 1960 Feb; 36(?):Comunicazioni 149-51. doi: NULL. [PMID: 13855507]