Biflorin (BioDeep_00000007102)

 

Secondary id: BioDeep_00000871048

human metabolite PANOMIX_OTCML-2023 natural product


代谢物信息卡片


5,7-dihydroxy-2-methyl-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one

化学式: C16H18O9 (354.0951)
中文名称:
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 45.83%

分子结构信息

SMILES: CC1=CC(=O)C2=C(O)C([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C(O)C=C2O1
InChI: InChI=1S/C16H18O9/c1-5-2-6(18)10-8(24-5)3-7(19)11(13(10)21)16-15(23)14(22)12(20)9(4-17)25-16/h2-3,9,12,14-17,19-23H,4H2,1H3/t9-,12-,14+,15-,16+/m1/s1

描述信息

Biflorin is an o-naphthoquinone isolated from Capraria biflora L. (Scrophulariaceae, a perennial shrub widely distributed in several countries of tropical America). Biflorin has cytotoxic and antioxidant potential, strongly inhibiting the growth of five tested tumor cell lines, especially the skin, breast and colon cancer cells with IC50 of 0.40, 0.43 and 0.88 micro/ml for B16, MCF-7 and HCT-8, respectively, while the antioxidant activity was assayed against autoxidation of oleic acid in a water/alcohol system. (PMID: 16042338).
Constituent of Eugenia caryophyllata (clove)

同义名列表

5 个代谢物同义名

5,7-dihydroxy-2-methyl-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4H-chromen-4-one; 6,9-Dimethyl-3-(4-methyl-3-pentenyl)naphtho(1,8-BC)pyran-7,8-dione; 6beta-C-Glucopyranosyl-5,7-dihydroxy-2-methylchromone; Biflorin; Biflorin



数据库引用编号

17 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)

43 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 AIMP2, ANXA5, BRAF, CDH1, CDH2, NOS2, PTGS2, STAT1, TP53
Peripheral membrane protein 2 ANXA5, PTGS2
Endosome membrane 1 NOTCH1
Endoplasmic reticulum membrane 3 NOTCH1, NRAS, PTGS2
Nucleus 8 AIMP2, BRAF, CDH1, JUND, NOS2, NOTCH1, STAT1, TP53
cytosol 10 AIMP2, ANXA5, BRAF, CDH1, NOS2, NOTCH1, NRAS, PRKCQ, STAT1, TP53
dendrite 1 STAT1
trans-Golgi network 1 CDH1
centrosome 1 TP53
nucleoplasm 6 CDH1, JUND, NOS2, NOTCH1, STAT1, TP53
RNA polymerase II transcription regulator complex 2 JUND, STAT1
Cell membrane 5 BRAF, CDH1, CDH2, NOTCH1, NRAS
Lipid-anchor 1 NRAS
Cytoplasmic side 1 NRAS
lamellipodium 2 CDH1, CDH2
Golgi apparatus membrane 1 NRAS
cell junction 2 CDH1, CDH2
cell surface 3 CDH2, MSLN, NOTCH1
glutamatergic synapse 3 BRAF, CDH1, NOTCH1
Golgi apparatus 3 CDH1, MSLN, NRAS
Golgi membrane 2 NOTCH1, NRAS
postsynapse 2 BRAF, CDH1
sarcolemma 2 ANXA5, CDH2
Cytoplasm, cytosol 2 AIMP2, NOS2
Presynapse 1 BRAF
acrosomal vesicle 1 NOTCH1
endosome 1 CDH1
plasma membrane 8 BRAF, CDH1, CDH2, MSLN, NOS2, NOTCH1, NRAS, PRKCQ
Membrane 8 AIMP2, ANXA5, CDH1, CDH2, MSLN, NOTCH1, NRAS, TP53
apical plasma membrane 2 CDH2, NOTCH1
axon 1 STAT1
basolateral plasma membrane 1 CDH2
caveola 1 PTGS2
extracellular exosome 3 ANXA5, CDH1, NRAS
endoplasmic reticulum 3 NOTCH1, PTGS2, TP53
perinuclear region of cytoplasm 3 CDH1, NOS2, STAT1
Schaffer collateral - CA1 synapse 1 NOTCH1
adherens junction 3 CDH1, CDH2, NOTCH1
apicolateral plasma membrane 1 CDH2
intercalated disc 1 CDH2
mitochondrion 2 BRAF, TP53
protein-containing complex 3 PTGS2, STAT1, TP53
intracellular membrane-bounded organelle 1 BRAF
Microsome membrane 1 PTGS2
postsynaptic density 1 CDH2
Single-pass type I membrane protein 3 CDH1, CDH2, NOTCH1
extracellular region 4 ANXA5, CDH1, MSLN, NOTCH1
cytoplasmic side of plasma membrane 1 CDH1
Mitochondrion matrix 1 TP53
mitochondrial matrix 1 TP53
transcription regulator complex 2 JUND, TP53
centriolar satellite 1 PRKCQ
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 TP53
nuclear membrane 1 CDH1
external side of plasma membrane 1 ANXA5
actin cytoskeleton 1 CDH1
nucleolus 2 STAT1, TP53
Cytoplasm, P-body 1 NOS2
P-body 1 NOS2
apical part of cell 1 CDH2
cell-cell junction 1 CDH2
presynaptic active zone membrane 1 CDH2
Cell membrane, sarcolemma 1 CDH2
Cytoplasm, perinuclear region 1 NOS2
Cytoplasm, cytoskeleton 1 TP53
focal adhesion 2 ANXA5, CDH2
Cell junction, adherens junction 2 CDH1, CDH2
flotillin complex 1 CDH1
Peroxisome 1 NOS2
peroxisomal matrix 1 NOS2
Nucleus, PML body 1 TP53
PML body 1 TP53
collagen-containing extracellular matrix 2 ANXA5, CDH2
fascia adherens 1 CDH2
lateral plasma membrane 1 CDH1
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
receptor complex 1 NOTCH1
Zymogen granule membrane 1 ANXA5
neuron projection 3 BRAF, CDH2, PTGS2
chromatin 3 JUND, STAT1, TP53
Late endosome membrane 1 NOTCH1
Golgi apparatus, trans-Golgi network 1 CDH1
site of double-strand break 1 TP53
tertiary granule membrane 1 NRAS
cell body 1 BRAF
side of membrane 1 MSLN
germ cell nucleus 1 TP53
replication fork 1 TP53
plasma membrane raft 1 CDH2
endoplasmic reticulum lumen 3 CDH2, MSLN, PTGS2
nuclear matrix 1 TP53
transcription repressor complex 2 JUND, TP53
anaphase-promoting complex 1 CDH1
postsynaptic density membrane 1 NOTCH1
immunological synapse 1 PRKCQ
aggresome 1 PRKCQ
vesicle membrane 1 ANXA5
[Isoform 2]: Nucleus 1 CDH1
[Isoform 1]: Nucleus 1 TP53
postsynaptic specialization membrane 1 CDH2
apical junction complex 1 CDH1
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
Cell junction, desmosome 2 CDH1, CDH2
desmosome 2 CDH1, CDH2
catenin complex 2 CDH1, CDH2
transcription factor AP-1 complex 1 JUND
cortical cytoskeleton 1 NOS2
endothelial microparticle 1 ANXA5
ISGF3 complex 1 STAT1
[Notch 1 intracellular domain]: Nucleus 1 NOTCH1
MAML1-RBP-Jkappa- ICN1 complex 1 NOTCH1


文献列表

  • Aluísio Marques da Fonseca, Neidelenio Baltazar Soares, Regilany Paulo Colares, Mauro Macedo de Oliveira, Larissa Santos Oliveira, Gabrielle Silva Marinho, Mira Raya Paula de Lima, Matheus Nunes da Rocha, Hélcio Silva Dos Santos, Emmanuel Silva Marinho. Naphthoquinones biflorin and bis-biflorin (Capraria biflora) as possible inhibitors of the fungus Candida auris polymerase: molecular docking, molecular dynamics, MM/GBSA calculations and in silico drug-likeness study. Journal of biomolecular structure & dynamics. 2023 Jan; ?(?):1-14. doi: 10.1080/07391102.2022.2163702. [PMID: 36597918]
  • Seung Jun Yang, Jong Hoon Ryu, Dae Sik Jang, Liang Yang, Hyo-Kyung Han. A sensitive LC-MS/MS method for the quantitative determination of biflorin in rat plasma and its application to pharmacokinetic studies. Journal of pharmaceutical and biomedical analysis. 2015 Nov; 115(?):272-6. doi: 10.1016/j.jpba.2015.07.032. [PMID: 26263054]
  • Edson R B Santana, João P Ferreira-Neto, Ricardo Yara, Kêsia X F R Sena, Adriana Fontes, Cláudia S A Lima. Biological activity and photostability of biflorin micellar nanostructures. Molecules (Basel, Switzerland). 2015 May; 20(5):8595-604. doi: 10.3390/molecules20058595. [PMID: 25985360]
  • Gabrielle G N S Wisintainer, Evelyne R B Simões, Telma L G Lemos, Sidnei Moura, Luciana G S Souza, Aluisio M Fonseca, Manoel Odorico Moraes, Claudia Pessoa, Mariana Roesch-Ely, João A P Henriques. Biflorin: an o-naphthoquinone of clinical significance. Anais da Academia Brasileira de Ciencias. 2014 Dec; 86(4):1907-14. doi: 10.1590/0001-3765201420140085. [PMID: 25590726]
  • Adriana Andrade Carvalho, Patrícia Marçal da Costa, Luciana Gregório Da Silva Souza, Telma Leda G Lemos, Ana Paula Negreiros Nunes Alves, Cláudia Pessoa, Manoel Odorico de Moraes. Inhibition of metastatic potential of B16-F10 melanoma cell line in vivo and in vitro by biflorin. Life sciences. 2013 Aug; 93(5-6):201-7. doi: 10.1016/j.lfs.2013.05.018. [PMID: 23743169]
  • Marne C Vasconcellos, Dinara J Moura, Renato M Rosa, Miriana S Machado, Temenouga N Guecheva, Izabel Villela, Bruna F Immich, Raquel C Montenegro, Aluísio M Fonseca, Telma L G Lemos, Maria Elisabete A Moraes, Jenifer Saffi, Letícia V Costa-Lotufo, Manoel O Moraes, João A P Henriques. Evaluation of the cytotoxic and antimutagenic effects of biflorin, an antitumor 1,4 o-naphthoquinone isolated from Capraria biflora L. Archives of toxicology. 2010 Oct; 84(10):799-810. doi: 10.1007/s00204-010-0567-z. [PMID: 20571778]
  • L Cai, C D Wu. Compounds from Syzygium aromaticum possessing growth inhibitory activity against oral pathogens. Journal of natural products. 1996 Oct; 59(10):987-90. doi: 10.1021/np960451q. [PMID: 8904847]