Mitraphylline (BioDeep_00000000413)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


SPIRO(3H-INDOLE-3,6(4AH)-(1H)PYRANO(3,4-F)INDOLIZINE)-4-CARBOXYLIC ACID, 1,2,5,5A,7,8,10,10A-OCTAHYDRO-1-METHYL-2-OXO-, METHYL ESTER, (1S,3R,4AS,5AS,10AR)-

化学式: C21H24N2O4 (368.1736)
中文名称: 帽柱叶碱, 帽柱木碱, 帽柱木菲碱
谱图信息: 最多检出来源 Homo sapiens(otcml) 15.12%

分子结构信息

SMILES: CC1C2CN3CCC4(C3CC2C(=CO1)C(=O)OC)C5=CC=CC=C5NC4=O
InChI: InChI=1S/C21H24N2O4/c1-12-14-10-23-8-7-21(16-5-3-4-6-17(16)22-20(21)25)18(23)9-13(14)15(11-27-12)19(24)26-2/h3-6,11-14,18H,7-10H2,1-2H3,(H,22,25)

描述信息

Mitraphylline is a member of indolizines.
Mitraphylline is a natural product found in Uncaria tomentosa, Mitragyna parvifolia, and other organisms with data available.
See also: Cats Claw (part of); Mitragyna speciosa leaf (part of).
Annotation level-1
Mitraphylline is the major pentacyclic oxindolic alkaloid presented in Uncaria tomentosa. Mitraphylline inhibits lipopolysaccharide-mediated activation of primary human neutrophils[1].
Mitraphylline is the major pentacyclic oxindolic alkaloid presented in Uncaria tomentosa. Mitraphylline inhibits lipopolysaccharide-mediated activation of primary human neutrophils[1].

同义名列表

20 个代谢物同义名

SPIRO(3H-INDOLE-3,6(4AH)-(1H)PYRANO(3,4-F)INDOLIZINE)-4-CARBOXYLIC ACID, 1,2,5,5A,7,8,10,10A-OCTAHYDRO-1-METHYL-2-OXO-, METHYL ESTER, (1S,3R,4AS,5AS,10AR)-; methyl (1S,4aS,5aS,6R,10aR)-1-methyl-2-oxospiro[1,4a,5,5a,7,8,10,10a-octahydropyrano[3,4-f]indolizine-6,3-1H-indole]-4-carboxylate; (1S,3R,4aS,5aS,10aR)-methyl 1-methyl-2-oxo-1,4a,5,5a,7,8,10,10a-octahydrospiro[indoline-3,6-pyrano[3,4-f]indolizine]-4-carboxylate; Formosanan-16-carboxylic acid, 19-methyl-2-oxo-, methyl ester, (19.alpha.)-; Formosanan-16-carboxylic acid, 19-methyl-2-oxo-, methyl ester, (19alpha)-; methyl (19alpha)-19-methyl-2-oxoformosanan-16-carboxylate; Methyl 19alpha-methyl-2-oxoformosanan-16-carboxylate; MITRAPHYLLINE (CONSTITUENT OF CATS CLAW) [DSC]; MITRAPHYLLINE (CONSTITUENT OF CATS CLAW); SEC-BUTYLMETHYLSULFIDE; Ajmalicine oxindole B; UNII-1H9SRL2456; Mitraphilline; Mitraphylline; Mitraphyllin; Rubradinine; Rubradinin; 1H9SRL2456; Isopteropodin; Mitraphylline



数据库引用编号

45 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)

62 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 9 ABCB1, BCL2, CAT, FDPS, FST, HPGDS, MAPK1, MAPK14, MARS1
Peripheral membrane protein 1 PTPMT1
Endosome membrane 1 CD14
Endoplasmic reticulum membrane 1 BCL2
Nucleus 6 BCL2, FST, MAPK1, MAPK14, NR1I2, PTPMT1
cytosol 7 BCL2, CAT, FDPS, HPGDS, MAPK1, MAPK14, MARS1
nuclear body 1 NR1I2
centrosome 1 MAPK1
nucleoplasm 5 FDPS, HPGDS, MAPK1, MAPK14, NR1I2
Cell membrane 6 ABCB1, CD14, FCGR3B, OPRD1, SELL, TNF
Multi-pass membrane protein 2 ABCB1, OPRD1
Synapse 1 MAPK1
cell surface 2 ABCB1, TNF
glutamatergic synapse 1 MAPK14
Golgi apparatus 2 CD14, MAPK1
mitochondrial inner membrane 1 PTPMT1
neuronal cell body 1 TNF
presynaptic membrane 1 OPRD1
Cytoplasm, cytosol 1 MARS1
plasma membrane 7 ABCB1, CD14, FCGR3B, MAPK1, OPRD1, SELL, TNF
synaptic vesicle membrane 1 OPRD1
Membrane 6 ABCB1, BCL2, CAT, FDPS, MARS1, OPRD1
apical plasma membrane 1 ABCB1
caveola 1 MAPK1
extracellular exosome 5 ABCB1, CAT, CD14, FCGR3B, MARS1
endoplasmic reticulum 1 BCL2
extracellular space 8 CD14, CXCL8, FST, IL17A, IL4, IL5, SELL, TNF
mitochondrion 5 BCL2, CAT, MAPK1, MAPK14, PTPMT1
protein-containing complex 2 BCL2, CAT
intracellular membrane-bounded organelle 2 CAT, HPGDS
Single-pass type I membrane protein 1 SELL
Secreted 5 CD14, CXCL8, IL17A, IL4, IL5
extracellular region 11 CAT, CD14, CXCL8, FCGR3B, FST, IL17A, IL4, IL5, MAPK1, MAPK14, TNF
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 2 BCL2, FCGR3B
mitochondrial outer membrane 1 BCL2
mitochondrial matrix 2 CAT, FDPS
transcription regulator complex 1 NR1I2
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 MAPK1
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 5 CD14, FCGR3B, IL17A, SELL, TNF
nucleolus 1 MARS1
Early endosome 1 MAPK1
recycling endosome 1 TNF
Single-pass type II membrane protein 1 TNF
Apical cell membrane 1 ABCB1
Mitochondrion inner membrane 1 PTPMT1
Matrix side 1 PTPMT1
Membrane raft 2 CD14, TNF
pore complex 1 BCL2
Cell junction, focal adhesion 1 MAPK1
Cytoplasm, cytoskeleton, spindle 1 MAPK1
focal adhesion 2 CAT, MAPK1
spindle 1 MAPK1
Peroxisome 2 CAT, FDPS
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
nuclear speck 1 MAPK14
Late endosome 1 MAPK1
neuron projection 1 OPRD1
chromatin 1 NR1I2
phagocytic cup 1 TNF
mitotic spindle 1 MAPK1
cytoskeleton 1 MAPK1
Nucleus, nucleolus 1 MARS1
spindle pole 1 MAPK14
Lipid-anchor, GPI-anchor 2 CD14, FCGR3B
Membrane, caveola 1 MAPK1
side of membrane 1 CD14
myelin sheath 1 BCL2
pseudopodium 1 MAPK1
intermediate filament cytoskeleton 1 NR1I2
lipopolysaccharide receptor complex 1 CD14
ficolin-1-rich granule lumen 3 CAT, MAPK1, MAPK14
secretory granule lumen 2 CAT, MAPK14
secretory granule membrane 3 CD14, FCGR3B, SELL
endoplasmic reticulum lumen 1 MAPK1
axon terminus 1 OPRD1
azurophil granule lumen 1 MAPK1
postsynaptic density membrane 1 OPRD1
neuronal dense core vesicle 1 OPRD1
external side of apical plasma membrane 1 ABCB1
aminoacyl-tRNA synthetase multienzyme complex 1 MARS1
dendrite membrane 1 OPRD1
[Tumor necrosis factor, soluble form]: Secreted 1 TNF
catalase complex 1 CAT
BAD-BCL-2 complex 1 BCL2
spine apparatus 1 OPRD1
[C-domain 2]: Secreted 1 TNF
[Tumor necrosis factor, membrane form]: Membrane 1 TNF
[C-domain 1]: Secreted 1 TNF


文献列表

  • Shyam H Kamble, Erin C Berthold, Tamara I King, Siva Rama Raju Kanumuri, Raluca Popa, Julius R Herting, Francisco León, Abhisheak Sharma, Lance R McMahon, Bonnie A Avery, Christopher R McCurdy. Pharmacokinetics of Eleven Kratom Alkaloids Following an Oral Dose of Either Traditional or Commercial Kratom Products in Rats. Journal of natural products. 2021 04; 84(4):1104-1112. doi: 10.1021/acs.jnatprod.0c01163. [PMID: 33620222]
  • Marcos Martins Gouvêa, Breno Henrique Pusceddu, Annibal Duarte Pereira Netto, Carlos Augusto de Freitas Peregrino, Elizabeth Valverde Macedo, Samanta Cardozo Mourão, Flávia Ferreira de Carvalho Marques. Isolation of mitraphylline from Uncaria tomentosa (Willd. ex Schult.) DC. barks and development of spectrophotometric method for total alkaloids determination in Cat's Claw samples. Phytochemical analysis : PCA. 2020 03; 31(2):262-272. doi: 10.1002/pca.2891. [PMID: 31769108]
  • Bruna C Azevedo, Mariana Roxo, Marcos C Borges, Herbenya Peixoto, Eduardo J Crevelin, Bianca W Bertoni, Silvia H T Contini, Adriana A Lopes, Suzelei C França, Ana M S Pereira, Michael Wink. Antioxidant Activity of an Aqueous Leaf Extract from Uncaria tomentosa and Its Major Alkaloids Mitraphylline and Isomitraphylline in Caenorhabditis elegans. Molecules (Basel, Switzerland). 2019 Sep; 24(18):. doi: 10.3390/molecules24183299. [PMID: 31510078]
  • Isabela Cristina G Honório, Juliana S Coppede, Piero G Delprete, Frederico Henrique S Costa, Mariana P C Telles, Ramilla S Braga, José Alexandre F Diniz-Filho, Valéria S C Correa, Suzelei C França, Ana Maria S Pereira, Bianca Waleria Bertoni. Genetic structure and chemical diversity in natural populations of Uncaria guianensis (Aubl.) J.F.Gmel. (Rubiaceae). PloS one. 2018; 13(10):e0205667. doi: 10.1371/journal.pone.0205667. [PMID: 30365495]
  • Isabela Cristina Gomes Honório, Bianca Waleria Bertoni, Mariana Pires de Campos Telles, Ramilla Dos Santos Braga, Suzelei de Castro França, Juliana da Silva Coppede, Valéria Siero Conde Correa, José Alexandre Felizola Diniz Filho, Ana Maria Soares Pereira. Genetic and chemical diversity of Uncaria tomentosa (Willd. ex. Schult.) DC. in the Brazilian Amazon. PloS one. 2017; 12(5):e0177103. doi: 10.1371/journal.pone.0177103. [PMID: 28475604]
  • Maninder Kaur, Manjinder Singh, Navriti Chadha, Om Silakari. Oxindole: A chemical prism carrying plethora of therapeutic benefits. European journal of medicinal chemistry. 2016 Nov; 123(?):858-894. doi: 10.1016/j.ejmech.2016.08.011. [PMID: 27543880]
  • Sergio Montserrat-de la Paz, Angeles Fernandez-Arche, Rocío de la Puerta, Ana M Quilez, Francisco J G Muriana, Maria Dolores Garcia-Gimenez, Beatriz Bermudez. Mitraphylline inhibits lipopolysaccharide-mediated activation of primary human neutrophils. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2016 Feb; 23(2):141-8. doi: 10.1016/j.phymed.2015.12.015. [PMID: 26926175]
  • Ashton D Lesiak, Robert B Cody, A John Dane, Rabi A Musah. Rapid detection by direct analysis in real time-mass spectrometry (DART-MS) of psychoactive plant drugs of abuse: the case of Mitragyna speciosa aka 'Kratom'. Forensic science international. 2014 Sep; 242(?):210-218. doi: 10.1016/j.forsciint.2014.07.005. [PMID: 25086346]
  • Vamshi K Manda, Bharathi Avula, Zulfiqar Ali, Ikhlas A Khan, Larry A Walker, Shabana I Khan. Evaluation of in vitro absorption, distribution, metabolism, and excretion (ADME) properties of mitragynine, 7-hydroxymitragynine, and mitraphylline. Planta medica. 2014 May; 80(7):568-76. doi: 10.1055/s-0034-1368444. [PMID: 24841968]
  • David Le, Melissa M Goggin, Gregory C Janis. Analysis of mitragynine and metabolites in human urine for detecting the use of the psychoactive plant kratom. Journal of analytical toxicology. 2012 Nov; 36(9):616-25. doi: 10.1093/jat/bks073. [PMID: 23024321]
  • R Rojas-Duran, G González-Aspajo, C Ruiz-Martel, G Bourdy, V H Doroteo-Ortega, J Alban-Castillo, G Robert, P Auberger, E Deharo. Anti-inflammatory activity of Mitraphylline isolated from Uncaria tomentosa bark. Journal of ethnopharmacology. 2012 Oct; 143(3):801-4. doi: 10.1016/j.jep.2012.07.015. [PMID: 22846434]
  • Gustavo Bertol, Luzia Franco, Brás Heleno de Oliveira. HPLC analysis of oxindole alkaloids in Uncaria tomentosa: sample preparation and analysis optimisation by factorial design. Phytochemical analysis : PCA. 2012 Mar; 23(2):143-51. doi: 10.1002/pca.1335. [PMID: 21809407]
  • Dolores García Giménez, Elena García Prado, Teresa Sáenz Rodríguez, Angeles Fernández Arche, Rocío De la Puerta. Cytotoxic effect of the pentacyclic oxindole alkaloid mitraphylline isolated from Uncaria tomentosa bark on human Ewing's sarcoma and breast cancer cell lines. Planta medica. 2010 Feb; 76(2):133-6. doi: 10.1055/s-0029-1186048. [PMID: 19724995]
  • E García Prado, M D García Gimenez, R De la Puerta Vázquez, J L Espartero Sánchez, M T Sáenz Rodríguez. Antiproliferative effects of mitraphylline, a pentacyclic oxindole alkaloid of Uncaria tomentosa on human glioma and neuroblastoma cell lines. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2007 Apr; 14(4):280-4. doi: 10.1016/j.phymed.2006.12.023. [PMID: 17296291]
  • Richa Pandey, Subhash C Singh, Madan M Gupta. Heteroyohimbinoid type oxindole alkaloids from Mitragyna parvifolia. Phytochemistry. 2006 Oct; 67(19):2164-9. doi: 10.1016/j.phytochem.2006.06.017. [PMID: 16872649]