Rescinnamine (BioDeep_00000000736)

 

Secondary id: BioDeep_00000404216, BioDeep_00000406602

human metabolite PANOMIX_OTCML-2023 blood metabolite Chemicals and Drugs natural product


代谢物信息卡片


methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-{[3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate

化学式: C35H42N2O9 (634.289)
中文名称: 利血那明
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 47.6%

分子结构信息

SMILES: COC(=O)C1C2CC3c4[nH]c5cc(OC)ccc5c4CCN3CC2CC(OC(=O)C=Cc2cc(OC)c(OC)c(OC)c2)C1OC
InChI: InChI=1S/C35H42N2O9/c1-40-21-8-9-22-23-11-12-37-18-20-15-29(46-30(38)10-7-19-13-27(41-2)33(43-4)28(14-19)42-3)34(44-5)31(35(39)45-6)24(20)17-26(37)32(23)36-25(22)16-21/h7-10,13-14,16,20,24,26,29,31,34,36H,11-12,15,17-18H2,1-6H3/t20-,24+,26-,29-,31+,34+/m1/s1

描述信息

Rescinnamine is only found in individuals that have used or taken this drug. It is an angiotensin-converting enzyme inhibitor used as an antihypertensive drug. It is an alkaloid obtained from Rauwolfia serpentina and other species of Rauwolfia. [Wikipedia]Rescinnamine Binds to and inhibits the angiotensin converting enzyme. Rescinnamine competes with angiotensin I for binding at the angiotensin-converting enzyme, blocking the conversion of angiotensin I to angiotensin II. Inhibition of ACE results in decreased plasma angiotensin II. As angiotensin II is a vasoconstrictor and a negative-feedback mediator for renin activity, lower concentrations result in a decrease in blood pressure and stimulation of baroreceptor reflex mechanisms, which leads to decreased vasopressor activity and to decreased aldosterone secretion.
C - Cardiovascular system > C02 - Antihypertensives > C02A - Antiadrenergic agents, centrally acting > C02AA - Rauwolfia alkaloids
C78274 - Agent Affecting Cardiovascular System > C270 - Antihypertensive Agent
Rescinnamine is an odorless white to cream colored crystalline powder. (NTP, 1992)
Rescinnamine is a methyl ester, an organic heteropentacyclic compound and an indole alkaloid. It has a role as an antihypertensive agent. It derives from a hydride of a yohimban.
Rescinnamine is a natural product found in Vinca major, Aspidosperma excelsum, and other organisms with data available.

同义名列表

119 个代谢物同义名

methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-{[3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3,13-diazapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁵,²⁰]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate; (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[1-oxo-3-(3,4,5-trimethoxyphenyl)prop-2-enoxy]-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylic acid methyl ester; Trimethoxycinnamoyl methyl reserpate; Methyl trimethoxycinnamoylreserpate; Rescinnamine; Rescinnamin; Reserpinine; Reserpinene; Recinnamine; Reserpinin; Anaprel; methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-{[3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4(9),5,7-tetraene-19-carboxylate; methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-{[3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate; Methyl 1alpha,2beta,3alpha,4,4aalpha,5,7,8,13,13bbeta,14,14aalpha-dodecahydro-2alpha,11-dimethoxy-3beta-(3,4,5-trimethoxycinnamoyloxy)benz(g)indolo(2,3-a)quinolizine-1beta-carboxylate; methyl (1R,15S,17R,18R,19S,20S)-6,18-dimethoxy-17-[(E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate; (3.BETA.,16.BETA.,17.ALPHA.,18.BETA.,20.ALPHA.)-11,17-DIMETHOXY-18-(((2E)-1-OXO-3-(3,4,5-TRIMETHOXYPHENYL)-2-PROPEN-1-YL)OXY)-YOHIMBAN-16-CARBOXYLIC ACID METHYL ESTER; Yohimban-16-carboxylic acid,17-dimethoxy-18-[[1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]oxy]-, methyl ester, (3.beta.,16.beta.,17.alpha.,18.beta.,20.alpha.)-; Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-(((2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)oxy)-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-; Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-((1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-oxy)-, methyl ester, (3beta,16beta,17alpha,18beta(E),20alpha)-; (3beta,16beta,17alpha,18beta,20alpha)-11,17-DIMETHOXY-18-(((2E)-1-OXO-3-(3,4,5-TRIMETHOXYPHENYL)-2-PROPEN-1-YL)OXY)-YOHIMBAN-16-CARBOXYLIC ACID METHYL ESTER; Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-((1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)oxy)-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-; methyl (3beta,16beta,17alpha,18beta,20alpha)-11,17-dimethoxy-18-({(2E)-3-[3,4,5-tris(methyloxy)phenyl]prop-2-enoyl}oxy)yohimban-16-carboxylate; Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-[[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl]oxy]-, methyl ester, (3b,16b,17a,18b,20a)-; Yohimban-16-carboxylicacid,11,17-dimethoxy-18-[[(2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propen-1-yl]oxy]-,methyl ester, (3b,16b,17a,18b,20a)-; 3beta,20alpha-Yohimban-16beta-carboxylic acid, 18beta-hydroxy-11,17alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate (ester), (E)-; 3-BETA,20-ALPHA-YOHIMBAN-16-BETA-CARBOXYLIC ACID, 18-BETA-HYDROXY-11, 17-ALPHA-DIMETHOXY-, METHYL ESTER, 3,4,5-TRIMETHOXYCINNAMATE (ESTER); 11,17alpha-Dimethoxy-18beta-((1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)oxy)-3beta,20alpha-yohimban-16beta-carboxylic acid methyl ester; 3-beta,20-alpha-Yohimban-16-beta-carboxylic acid, 18-beta-hydroxy-11,17-alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate (ester); 3beta,20alpha-Yohimban-16beta-carboxylic acid, 18beta-hydroxy-11,17alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate (ester); methyl 11,17alpha-dimethoxy-18beta-(((2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl)oxy)-3beta,20alpha-yohimban-16beta-carboxylate; methyl 11,17alpha-dimethoxy-18beta-{[(2E)-3-(3,4,5-trimethoxyphenyl)prop-2-enoyl]oxy}-3beta,20alpha-yohimban-16beta-carboxylate; Benz[g]indolo[2, 1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydro-3-hydroxy-2,11-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate; 11,17-DIMETHOXY-18-((1-OXO-3-(3,4,5-TRIMETHOXYPHENYL)-2-PROPENYL)OXY)-3,20-YOHIMBAN-16-CARBOXYLIC ACID METHYL ESTER; 11,17-Dimethoxy-18-[[1-oxo-3-3,4,5-trimethoxyphenyl)-2-propenyl]oxy]-3,20-yohimban-16-carboxylic acid methyl ester; 3.beta., 18.beta.-hydroxy-11,17.alpha.-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate (ester); Methyl 18.beta.-hydroxy-11,17.alpha.-dimethoxy-3.beta.,20.alpha.-yohimban-16.beta.-carboxylate; Methyl 18beta-hydroxy-11,17alpha-dimethoxy-3beta,20alpha-yohimban-16beta-carboxylate; 3,4,5-Trimethylcinnamic acid, ester with methyl reserpate; 3,4,5-trimethoxycinnamic acid ester of methyl reserpate; O-(3,4,5-Trimethoxy-trans-cinnamoyl) methyl reserpate; Methyl reserpate 3,4,5-trimethoxycinnamic acid ester; Reserpic acid methyl ester 3,4,5-trimethoxycinnamate; Trimethoxy cinnamoyl reserpate de methyl [French]; METHYL 18-O-(3,4,5-TRIMETHOXYCINNAMOYL) RESERPATE; Methyl 18-O-(3,4,5-trimethoxycinnamoyl)reserpate; METHYL 18-O-(3,4,5-TRIMETHOXYCINNAMOYL RESERPATE; 3,4,5-Trimethoxycinnamic acid, methyl reserpate; 3,5-Trimethoxycinnamic acid, methyl reserpate; 4-25-00-01323 (Beilstein Handbook Reference); METHYL 3,4,5-TRIMETHOXYCINNAMOYL RESERPATE; 3,4,5-Trimethoxycinnamoyl methyl reserpate; 3,4,5-Trimethylcinnamoyl methyl reserpate; Trimethoxy cinnamoyl reserpate de methyl; 3,5-Trimethoxycinnamoyl methyl reserpate; Rescinnamine [INN:BAN:JAN:NF]; Reserpinine (C35 alkaloid); RESCINNAMINE [ORANGE BOOK]; Rescinamina [INN-Spanish]; Resepinine (C35 alkaloid); Rescinnaminum (INN-Latin); Rescinamina (INN-Spanish); Rescinnaminum [INN-Latin]; Rescinnamine (JAN/INN); RESCINNAMINE [WHO-DD]; RESCINNAMINE (MART.); RESCINNAMINE [MART.]; RESCINNAMINE [VANDF]; RESCINNAMINE [HSDB]; Rescinnamina [DCIT]; RESCINNAMINE [INN]; RESCINNAMINE [JAN]; Rescinnamine (VAN); Tsuruselpi S (TN); Prestwick3_000568; Prestwick2_000568; RESCINNAMINE [MI]; UNII-Q6W1F7DJ2D; BPBio1_000392; MEGxp0_001952; Rescinnaminum; Rescinnamina; ACon1_002115; Normorescina; Tox21_110611; Tsuruselpi S; Recitensina; Reskinnamin; Rescinamina; Apoterin S; Raurescine; Q6W1F7DJ2D; Scinnamina; Cinnaloid; Resealoid; Rescaloid; AI3-52763; Raurescin; Rescinpal; Rescitens; Paresinan; Rescisan; Tenamine; Cinatabs; Rescidan; Rescamin; Cinamine; Raupyrol; Apoterin; Cinnasil; Resipal; Cartric; Moderil; C02AA01; Anapral; Tuareg; Rescin; Apolon; Rozex; Rescinnamine



数据库引用编号

27 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)

26 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 5 DBH, HDAC9, MSI2, SREBF1, TXNRD3
Endoplasmic reticulum membrane 1 SREBF1
Nucleus 5 HDAC9, MSH2, MSH6, SREBF1, TXNRD3
cytosol 5 MSH6, MSI2, RRM1, SREBF1, TXNRD3
nucleoplasm 5 HDAC9, MSH2, MSH6, SREBF1, TXNRD3
Multi-pass membrane protein 1 SREBF1
Golgi apparatus membrane 1 SREBF1
Synapse 1 DBH
Golgi apparatus 1 MSH6
Golgi membrane 1 SREBF1
neuronal cell body 1 RRM1
plasma membrane 1 BCHE
Membrane 3 DBH, MSH2, RRM1
endoplasmic reticulum 3 DBH, SREBF1, TXNRD3
extracellular space 2 BCHE, DBH
mitochondrion 2 RRM1, TXNRD3
protein-containing complex 1 SREBF1
intracellular membrane-bounded organelle 3 DBH, MSH6, MSI2
Secreted 2 BCHE, DBH
extracellular region 2 BCHE, DBH
transcription regulator complex 1 HDAC9
centriolar satellite 1 DBH
Single-pass type II membrane protein 1 DBH
chromatin 2 MSH6, SREBF1
cell projection 1 RRM1
Chromosome 2 MSH2, MSH6
chromosome, telomeric region 1 MSH2
blood microparticle 1 BCHE
nuclear envelope 2 RRM1, SREBF1
Cytoplasmic vesicle membrane 1 SREBF1
Microsome 1 TXNRD3
secretory granule lumen 1 DBH
secretory granule membrane 1 DBH
endoplasmic reticulum lumen 1 BCHE
histone methyltransferase complex 1 HDAC9
histone deacetylase complex 1 HDAC9
ER to Golgi transport vesicle membrane 1 SREBF1
nuclear envelope lumen 1 BCHE
Cytoplasmic vesicle, secretory vesicle membrane 1 DBH
Cytoplasmic vesicle, COPII-coated vesicle membrane 1 SREBF1
Cytoplasmic vesicle, secretory vesicle, chromaffin granule lumen 1 DBH
chromaffin granule lumen 1 DBH
transport vesicle membrane 1 DBH
[Soluble dopamine beta-hydroxylase]: Cytoplasmic vesicle, secretory vesicle lumen 1 DBH
Cytoplasmic vesicle, secretory vesicle, chromaffin granule membrane 1 DBH
chromaffin granule membrane 1 DBH
MutSbeta complex 1 MSH2
ribonucleoside-diphosphate reductase complex 1 RRM1
[Sterol regulatory element-binding protein 1]: Endoplasmic reticulum membrane 1 SREBF1
[Processed sterol regulatory element-binding protein 1]: Nucleus 1 SREBF1
[Isoform SREBP-1aDelta]: Nucleus 1 SREBF1
[Isoform SREBP-1cDelta]: Nucleus 1 SREBF1
MutSalpha complex 2 MSH2, MSH6


文献列表

  • Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
  • Brent Wiens, Vincenzo De Luca. Molecular and biochemical characterization of a benzenoid/phenylpropanoid meta/para-O-methyltransferase from Rauwolfia serpentina roots. Phytochemistry. 2016 Dec; 132(?):5-15. doi: 10.1016/j.phytochem.2016.10.004. [PMID: 27771009]
  • Mokutima A Eluwa, Matilda T Udoaffah, Moses B G Vulley, Theresa B Ekanem, Amabe O Akpantah, Olaitan A Asuquo, Moses B Ekong. Comparative study of teratogenic potentials of crude ethanolic root bark and leaf extract of Rauwolfia vomitoria (apocynaceae) on the fetal heart. North American journal of medical sciences. 2010 Dec; 2(12):592-5. doi: 10.4297/najms.2010.2592. [PMID: 22558573]
  • Atsuko Itoh, Tomoko Kumashiro, Machiko Yamaguchi, Naotaka Nagakura, Yoshiyuki Mizushina, Toyoyuki Nishi, Takao Tanahashi. Indole alkaloids and other constituents of Rauwolfia serpentina. Journal of natural products. 2005 Jun; 68(6):848-52. doi: 10.1021/np058007n. [PMID: 15974606]
  • Chung-Yi Wu, Jia-Tsrong Jan, Shiou-Hwa Ma, Chih-Jung Kuo, Hsueh-Fen Juan, Yih-Shyun E Cheng, Hsien-Hua Hsu, Hsuan-Cheng Huang, Douglass Wu, Ashraf Brik, Fu-Sen Liang, Rai-Shung Liu, Jim-Min Fang, Shui-Tein Chen, Po-Huang Liang, Chi-Huey Wong. Small molecules targeting severe acute respiratory syndrome human coronavirus. Proceedings of the National Academy of Sciences of the United States of America. 2004 Jul; 101(27):10012-7. doi: 10.1073/pnas.0403596101. [PMID: 15226499]
  • M A Anderson, T Wachs, J D Henion. Quantitative ionspray liquid chromatographic/tandem mass spectrometric determination of reserpine in equine plasma. Journal of mass spectrometry : JMS. 1997 Feb; 32(2):152-8. doi: 10.1002/(sici)1096-9888(199702)32:2<152::aid-jms456>3.0.co;2-w. [PMID: 9102199]
  • H KANEKO, R FUJIMOTO, K NAMBA, K HAYASHI. [Analysis of alkaloids in the domestic Rauwolfia serpentina root. II. Determination of reserpine and rescinnamine]. Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan. 1962 Nov; 82(?):1493-6. doi: ". [PMID: 13962199]
  • L VERCILLO, A GIRALDI, G MOREO. [Action of rescinnamine, Rauwolfia serpentina alkdloid, on renal hemodynamics in patients with arterial hypertension]. Rassegna internazionale di clinica e terapia. 1961 Jan; 41(?):51-8. doi: NULL. [PMID: 13780798]
  • J LA BARRIE, M J HANS. [Research on urinary metabolites of serotonin after the administration of decamethoxydeserpidine and rescinnamine]. Comptes rendus des seances de la Societe de biologie et de ses filiales. 1960; 154(?):474-5. doi: . [PMID: 14413108]
  • D BANES, A E HOUK, J WOLFF. The reserpine, rescinnamine, and deserpidine content of Rauwolfia roots. Journal of the American Pharmaceutical Association. American Pharmaceutical Association. 1958 Sep; 47(9):625-7. doi: . [PMID: 13575224]