Dicentrine (BioDeep_00000000504)

 

Secondary id: BioDeep_00000171521, BioDeep_00000267970

natural product PANOMIX_OTCML-2023 Antitumor activity


代谢物信息卡片


(12S)-16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaene

化学式: C20H21NO4 (339.1471)
中文名称: 荷苞牡丹碱, 荷包牡丹碱, D-荷包牡丹碱
谱图信息: 最多检出来源 Viridiplantae(plant) 100%

分子结构信息

SMILES: CN1C2C3=C(C(C=C(OC)C(OC)=C4)=C4C2)C5=C(OCO5)C=C3CC1
InChI: InChI=1S/C20H21NO4/c1-21-5-4-11-7-17-20(25-10-24-17)19-13-9-16(23-3)15(22-2)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3

描述信息

Dicentrine is an aporphine alkaloid.
Dicentrine is a natural product found in Cissampelos pareira, Stephania abyssinica, and other organisms with data available.
Dicentrine is an anticancer compound isolated from Lindera, a species of flowering plants.
Dicentrine is a natural product isolated from the plant Stephania epigaea Lo with antihypertensive effect. Dicentrine is an α1-adrenoceptor antagonist which has effective against human hyperplastic prostates[1].

同义名列表

36 个代谢物同义名

(12S)-16,17-dimethoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14,16,18-hexaene; 5H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (S)- (9CI); 5H-BENZO(G)-1,3-BENZODIOXOLO(6,5,4-DE)QUINOLINE, 6,7,7A,8-TETRAHYDRO-10,11-DIMETHOXY-7-METHYL-, (7AS)-; 5H-Benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (S)-; 5H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (S)-; 10,11-Dimethoxy-7-methyl-6,7,7a,8-tetrahydro-5H-[1,3]benzodioxolo[6,5,4-de]benzo[g]quinoline-, (S)-; 5H-Benzo[g]-1,5,4-de]quinoline, 6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (S)-; 6a-alpha-Aporphine, 9,10-dimethoxy-1,2-(methylenedioxy)-; 9,10-Dimethoxy-1,2-(methylenedioxy)-6a.alpha.-aporphine; 6aalpha-Aporphine, 9,10-dimethoxy-1,2-(methylenedioxy)-; 6a.alpha.-Aporphine,10-dimethoxy-1,2-(methylenedioxy)-; 4-27-00-06486 (Beilstein Handbook Reference); 9,10-Dimethoxy-1,2-(methylenedioxy)aporphine; 1,2-Methylenedioxy-9,10-dimethoxyaporphine; dicentrine nitrate, (S)-isomer; 9,2-(methylenedioxy)aporphine; YJWBWQWUHVXPNC-AWEZNQCLSA-N; (S)-form;(+)-Dicentrine; O,N-Dimethyllitseferine; dicentrine, (R)-isomer; DICENTRINE D-FORM [MI]; (R)-(-)-dicentrine; dicentrine, (-)-; DICENTRINE, (+)-; DICENTRINE [MI]; UNII-J2ZGT5M0N7; (+)-dicentrine; Dicentrine-(+); L-dicentrine; D-Dicentrine; J2ZGT5M0N7; Dicentrine; Dicentrin; Eximine; (+/-)-Dicentrine; Dicentrine



数据库引用编号

23 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)

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 13 ADRA1A, AHR, AIMP2, AXIN2, BCL2L1, BIRC3, BRCA1, CASP8, EGFR, ELANE, MAPK8, PTGS2, TNK1
Peripheral membrane protein 2 PTGS2, TNK1
Endosome membrane 1 EGFR
Endoplasmic reticulum membrane 2 EGFR, PTGS2
Mitochondrion membrane 1 BCL2L1
Nucleus 10 ADRA1A, AHR, AIMP2, AXIN2, BIRC3, BRCA1, CASP8, EGFR, JUND, MAPK8
cytosol 9 ADRA1A, AHR, AIMP2, AXIN2, BCL2L1, BIRC3, CASP8, ELANE, MAPK8
dendrite 2 HTR2A, HTR2C
nuclear body 1 BRCA1
phagocytic vesicle 1 ELANE
centrosome 2 AXIN2, BCL2L1
nucleoplasm 7 ADRA1A, AHR, BIRC3, BRCA1, CASP8, JUND, MAPK8
RNA polymerase II transcription regulator complex 1 JUND
Cell membrane 7 ADRA1A, EGFR, HTR2A, HTR2C, OPRD1, TRPA1, TRPV1
Cytoplasmic side 1 BCL2L1
lamellipodium 1 CASP8
ruffle membrane 1 EGFR
Cell projection, axon 1 HTR2A
Early endosome membrane 1 EGFR
Multi-pass membrane protein 6 ADRA1A, HTR2A, HTR2C, OPRD1, TRPA1, TRPV1
Synapse 2 HTR2C, MAPK8
cell junction 1 EGFR
cell surface 2 EGFR, ELANE
dendritic shaft 1 HTR2A
glutamatergic synapse 2 EGFR, HTR2A
Golgi membrane 1 EGFR
mitochondrial inner membrane 1 BCL2L1
neuronal cell body 2 HTR2A, TRPV1
presynaptic membrane 2 HTR2A, OPRD1
Cytoplasm, cytosol 2 AIMP2, BCL2L1
Presynapse 1 HTR2A
endosome 1 EGFR
plasma membrane 10 ADRA1A, AXIN2, BRCA1, EGFR, HTR2A, HTR2C, OPRD1, TNK1, TRPA1, TRPV1
synaptic vesicle membrane 2 BCL2L1, OPRD1
Membrane 7 AIMP2, BRCA1, EGFR, OPRD1, TNK1, TRPA1, TRPV1
apical plasma membrane 1 EGFR
axon 2 HTR2A, MAPK8
basolateral plasma membrane 1 EGFR
caveola 3 ADRA1A, HTR2A, PTGS2
extracellular exosome 1 ELANE
endoplasmic reticulum 2 BCL2L1, PTGS2
extracellular space 3 EGFR, ELANE, IL6
perinuclear region of cytoplasm 1 EGFR
mitochondrion 2 BCL2L1, CASP8
protein-containing complex 6 AHR, BIRC3, BRCA1, CASP8, EGFR, PTGS2
intracellular membrane-bounded organelle 1 ADRA1A
Microsome membrane 1 PTGS2
Single-pass type I membrane protein 1 EGFR
Secreted 1 IL6
extracellular region 2 ELANE, IL6
Mitochondrion outer membrane 1 BCL2L1
Single-pass membrane protein 1 BCL2L1
mitochondrial outer membrane 2 BCL2L1, CASP8
Mitochondrion matrix 1 BCL2L1
mitochondrial matrix 1 BCL2L1
transcription regulator complex 2 AHR, JUND
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 BCL2L1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 BCL2L1
Nucleus membrane 2 ADRA1A, BCL2L1
Bcl-2 family protein complex 1 BCL2L1
nuclear membrane 3 ADRA1A, BCL2L1, EGFR
external side of plasma membrane 1 TRPV1
beta-catenin destruction complex 1 AXIN2
cytoplasmic vesicle 1 HTR2A
postsynaptic membrane 2 HTR2A, TRPV1
Cell projection, lamellipodium 1 CASP8
Membrane raft 1 EGFR
focal adhesion 1 EGFR
GABA-ergic synapse 1 TRPV1
intracellular vesicle 1 EGFR
collagen-containing extracellular matrix 1 ELANE
secretory granule 1 ELANE
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Postsynaptic cell membrane 1 TRPV1
receptor complex 1 EGFR
Cell projection, neuron projection 1 TRPV1
neuron projection 2 OPRD1, PTGS2
chromatin 2 AHR, JUND
stereocilium bundle 1 TRPA1
Chromosome 1 BRCA1
cytoskeleton 1 CASP8
[Isoform 5]: Cytoplasm 1 BRCA1
Membrane, caveola 2 ADRA1A, HTR2A
lateral element 1 BRCA1
aryl hydrocarbon receptor complex 1 AHR
cell body fiber 1 HTR2A
Cell projection, dendrite 1 HTR2A
cell body 1 CASP8
ubiquitin ligase complex 1 BRCA1
basal plasma membrane 1 EGFR
synaptic membrane 1 EGFR
endoplasmic reticulum lumen 2 IL6, PTGS2
transcription repressor complex 2 ELANE, JUND
male germ cell nucleus 1 BRCA1
axon terminus 1 OPRD1
specific granule lumen 1 ELANE
XY body 1 BRCA1
azurophil granule lumen 1 ELANE
postsynaptic density membrane 1 OPRD1
neuronal dense core vesicle 1 OPRD1
neurofilament 1 HTR2A
clathrin-coated endocytic vesicle membrane 1 EGFR
ribonucleoprotein complex 1 BRCA1
basal dendrite 1 MAPK8
CD95 death-inducing signaling complex 1 CASP8
death-inducing signaling complex 1 CASP8
ripoptosome 1 CASP8
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
intracellular non-membrane-bounded organelle 1 BRCA1
dendrite membrane 1 OPRD1
DNA repair complex 1 BRCA1
Cytoplasmic vesicle, phagosome 1 ELANE
BRCA1-C complex 1 BRCA1
Cell projection, dendritic spine membrane 1 TRPV1
dendritic spine membrane 1 TRPV1
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
transcription factor AP-1 complex 1 JUND
interleukin-6 receptor complex 1 IL6
nuclear aryl hydrocarbon receptor complex 1 AHR
G protein-coupled serotonin receptor complex 2 HTR2A, HTR2C
cytosolic aryl hydrocarbon receptor complex 1 AHR
BRCA1-A complex 1 BRCA1
BRCA1-B complex 1 BRCA1
BRCA1-BARD1 complex 1 BRCA1
gamma-tubulin ring complex 1 BRCA1
nuclear ubiquitin ligase complex 1 BRCA1
spine apparatus 1 OPRD1
[Isoform Bcl-X(L)]: Mitochondrion inner membrane 1 BCL2L1


文献列表

  • Tharita Kitisripanya, Jukrapun Komaikul, Nirachara Tawinkan, Chuennapha Atsawinkowit, Waraporn Putalun. Dicentrine production in callus and cell suspension cultures of Stephania venosa. Natural product communications. 2013 Apr; 8(4):443-5. doi: . [PMID: 23738448]
  • Deise Prehs Montrucchio, Marina Machado Córdova, Adair Roberto Soares Santos. Plant derived aporphinic alkaloid S-(+)-dicentrine induces antinociceptive effect in both acute and chronic inflammatory pain models: evidence for a role of TRPA1 channels. PloS one. 2013; 8(7):e67730. doi: 10.1371/journal.pone.0067730. [PMID: 23861794]
  • Deise Prehs Montrucchio, Obdulio Gomes Miguel, Sandra Maria Warumby Zanin, Gabriel Araujo da Silva, Alcíbia Maia Cardozo, Adair Roberto Soares Santos. Antinociceptive effects of a chloroform extract and the alkaloid dicentrine isolated from fruits of Ocotea puberula. Planta medica. 2012 Sep; 78(14):1543-8. doi: 10.1055/s-0032-1315026. [PMID: 22815198]
  • Yi-Chun Lai, Tzong-Fu Kuo, Chien-Kuang Chen, Han-Ju Tsai, Shoei-Sheng Lee. Metabolism of dicentrine: identification of the phase I and phase II metabolites in miniature pig urine. Drug metabolism and disposition: the biological fate of chemicals. 2010 Oct; 38(10):1714-22. doi: 10.1124/dmd.110.033795. [PMID: 20622045]
  • Walmir S Garcez, Fernanda R Garcez, Lilliam M G E da Silva, Lidilhone Hamerski. Larvicidal activity against Aedes aegypti of some plants native to the West-Central region of Brazil. Bioresource technology. 2009 Dec; 100(24):6647-50. doi: 10.1016/j.biortech.2009.06.092. [PMID: 19664915]
  • Waraporn Putalun, Gorawit Yusakul, Denpong Patanasethanont. Dicentrine production from a hairy roots culture of Stephania suberosa. Zeitschrift fur Naturforschung. C, Journal of biosciences. 2009 Sep; 64(9-10):692-6. doi: 10.1515/znc-2009-9-1014. [PMID: 19957438]
  • V Badireenath Konkimalla, Venkatramana Laxminarayana Suhas, Nagasuma R Chandra, Erich Gebhart, Thomas Efferth. Diagnosis and therapy of oral squamous cell carcinoma. Expert review of anticancer therapy. 2007 Mar; 7(3):317-29. doi: 10.1586/14737140.7.3.317. [PMID: 17338652]
  • R L Huang, C C Chen, Y L Huang, J C Ou, C P Hu, C F Chen, C Chang. Anti-tumor effects of d-dicentrine from the root of Lindera megaphylla. Planta medica. 1998 Apr; 64(3):212-5. doi: 10.1055/s-2006-957411. [PMID: 9581516]
  • K S Chen, Y C Wu, C M Teng, F N Ko, T S Wu. Bioactive alkaloids from Illigera luzonensis. Journal of natural products. 1997 Jun; 60(6):645-7. doi: 10.1021/np9700735. [PMID: 9214740]
  • T H Tsai, T R Tsai, C J Chou, C F Chen. Determination of dicentrine in rat plasma by high-performance liquid chromatography and its application to pharmacokinetics. Journal of chromatography. B, Biomedical applications. 1996 Jun; 681(2):277-81. doi: 10.1016/0378-4347(95)00553-6. [PMID: 8811437]
  • S M Yu, Y F Kang, C C Chen, C M Teng. Effects of dicentrine on haemodynamic, plasma lipid, lipoprotein level and vascular reactivity in hyperlipidaemic rats. British journal of pharmacology. 1993 Apr; 108(4):1055-61. doi: 10.1111/j.1476-5381.1993.tb13505.x. [PMID: 8485617]
  • S M Yu, S Y Hsu, F N Ko, C C Chen, Y L Huang, T F Huang, C M Teng. Haemodynamic effects of dicentrine, a novel alpha 1-adrenoceptor antagonist: comparison with prazosin in spontaneously hypertensive and normotensive Wistar-Kyoto rats. British journal of pharmacology. 1992 Aug; 106(4):797-801. doi: 10.1111/j.1476-5381.1992.tb14415.x. [PMID: 1356567]
  • C M Teng, S M Yu, F N Ko, C C Chen, Y L Huang, T F Huang. Dicentrine, a natural vascular alpha 1-adrenoceptor antagonist, isolated from Lindera megaphylla. British journal of pharmacology. 1991 Nov; 104(3):651-6. doi: 10.1111/j.1476-5381.1991.tb12484.x. [PMID: 1686739]