Dmask (BioDeep_00000000519)

 

Secondary id: BioDeep_00000173730, BioDeep_00000268069, BioDeep_00000866033, BioDeep_00001867517, BioDeep_00001883577

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


2-Butenoic acid, 3-methyl-, 1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester, (+)-

化学式: C21H22O6 (370.1416)
中文名称: BETA,BETA-二甲基丙烯酰阿卡宁, BATA,BATA-二甲基丙烯酰紫草素, β,β-二甲基丙烯酰紫草素, β,β-二甲基丙烯酰阿卡宁, (β,β-二甲基丙烯酰基)紫草素, β,β′－二甲基丙烯酰阿卡宁
谱图信息: 最多检出来源 Homo sapiens(blood) 66.95%

分子结构信息

SMILES: C/C(C)=C\C(OC(C(C1=O)=CC(C2=C1C(O)=CC=C2O)=O)C/C=C(C)\C)=O
InChI: InChI=1S/C21H22O6/c1-11(2)5-8-17(27-18(25)9-12(3)4)13-10-16(24)19-14(22)6-7-15(23)20(19)21(13)26/h5-7,9-10,17,22-23H,8H2,1-4H3

描述信息

Dmask is a natural product found in Arnebia hispidissima with data available.
Beta,beta-Dimethylacrylshikonin is a hydroxy-1,4-naphthoquinone.
beta,beta-Dimethylacrylshikonin is a natural product found in Alkanna cappadocica, Lithospermum erythrorhizon, and other organisms with data available.
(Rac)-Arnebin 1 ((Rac)-β,β-Dimethylacrylalkannin) is the racemate of β,β-Dimethylacrylalkannin and/or β,β-Dimethylacrylshikonin. β,β-Dimethylacrylalkannin and β,β-Dimethylacrylshikonin are napthoquinones isolated from Arnebia nobilis. β,β-Dimethylacrylshikonin has anti-tumor activity[1].
(Rac)-Arnebin 1 ((Rac)-β,β-Dimethylacrylalkannin) is the racemate of β,β-Dimethylacrylalkannin and/or β,β-Dimethylacrylshikonin. β,β-Dimethylacrylalkannin and β,β-Dimethylacrylshikonin are napthoquinones isolated from Arnebia nobilis. β,β-Dimethylacrylshikonin has anti-tumor activity[1].
(Rac)-Arnebin 1 ((Rac)-β,β-Dimethylacrylalkannin) is the racemate of β,β-Dimethylacrylalkannin and/or β,β-Dimethylacrylshikonin. β,β-Dimethylacrylalkannin and β,β-Dimethylacrylshikonin are napthoquinones isolated from Arnebia nobilis. β,β-Dimethylacrylshikonin has anti-tumor activity[1].
β,β-Dimethylacrylalkannin (Arnebin 1) is a napthoquinone isolated from Alkanna cappadocica , increases collagen and involucrin content in skin cells[1].
β,β-Dimethylacrylalkannin (Arnebin 1) is a napthoquinone isolated from Alkanna cappadocica , increases collagen and involucrin content in skin cells[1].
β,β-Dimethylacrylalkannin (Arnebin 1) is a napthoquinone isolated from Alkanna cappadocica , increases collagen and involucrin content in skin cells[1].
β,β-Dimethylacrylshikonin (Isoarnebin I) is a naphthoquinone derivative isolated from Lithospermum erythrorhizon Sieb. et Zucc. , promotes angiogenesis by inducing eNOS, VEGF and HIF-1α expression through the PI3K-dependent pathway.β,β-Dimethylacrylshikonin has anti-tumor activity[1].
β,β-Dimethylacrylshikonin (Isoarnebin I) is a naphthoquinone derivative isolated from Lithospermum erythrorhizon Sieb. et Zucc. , promotes angiogenesis by inducing eNOS, VEGF and HIF-1α expression through the PI3K-dependent pathway.β,β-Dimethylacrylshikonin has anti-tumor activity[1].
β,β-Dimethylacrylshikonin (Isoarnebin I) is a naphthoquinone derivative isolated from Lithospermum erythrorhizon Sieb. et Zucc. , promotes angiogenesis by inducing eNOS, VEGF and HIF-1α expression through the PI3K-dependent pathway.β,β-Dimethylacrylshikonin has anti-tumor activity[1].

同义名列表

46 个代谢物同义名

2-Butenoic acid, 3-methyl-, 1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester, (+)-; 2-Butenoic acid, 3-methyl-, 1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester; Crotonic acid, 3-methyl-, ester with 5,8-dihydroxy-2-(1-hydroxy-4-methyl-3-pentenyl)-1,4-naphthoquinone; 2-Butenoic acid, 1-(5,8-dihydro- 1,4-dihydroxy-5,8-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester; 1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbut-2-enoate; 1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-4-methyl-3-pentenyl 3-methyl-2-butenoate #; 5,8-Dihydroxy-2-[1-(beta,beta-dimethylacryloyloxy)-4-methyl-3-pentenyl]-1,4-naphthalenedione; [1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-methylbut-2-enoate; Dimethylacrylshikonin;(Beta,beta-dimethylacryl)shikonin; beta, beta-dimethylacrylshikonin, (+)-isomer; beta, beta-dimethylacrylshikonin, (-)-isomer; (c)micro,(c)micro-Dimethylacrylalkannin; Shikonin .beta.,.beta.-dimethylacrylate; .beta.,.beta.-Dimethylacrylshikonin; (beta,beta-Dimethylacryl)shikonin; beta, beta-dimethylacrylshikonin; Alkanin,.beta.-dimethylacrylate; Alkanin b,b-dimethylacrylate; β,β-dimethyl-acry-lalkannin; β,β-Dimethylacrylalkannin; β,β-Dimethylacrylshikonin; (Rac)-Arnebin 1; Isoarnebin I; NCI60_000890; Arnebin 1; arnebin I; Arnebin; Dmask; β, β-dimethylacrylalkannin; Alkannin beta,beta-dimethylacrylate; 2-Butenoic acid, 3-methyl-, 1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester, (R)-; 2-Butenoic acid, 3-methyl-, (1R)-1-(1,4-dihydro-5,8-dihydroxy-1,4-dioxo-2-naphthalenyl)-4-methyl-3-pentenyl ester; (1R)-1-(5,8-Dihydroxy-1,4-dioxo-1,4-dihydro-2-naphthalenyl)-4-methyl-3-pentenyl 3-methyl-2-butenoate, AldrichCPR; (R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-en-1-yl 3-methylbut-2-enoate; (R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 3-methylbut-2-enoate; [(1R)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 3-methylbut-2-enoate; |A,|A inverted exclamation marka pound-dimethylacrylalkannin; Shikonin beta,beta-dimethylacrylate; beta,beta-Dimethylacrylshikonin; b, b-Dimethylacrylshikonin; Dimethylacrylshikonin; dimethylacrylalkannin; beta,beta-Dimethylacrylshikonin; (Rac)-β,β-Dimethylacrylalkannin; (Rac)-β,β-?Dimethylacrylshikonin; Alkannin beta,beta-dimethylacrylate



数据库引用编号

30 个数据库交叉引用编号

分类词条

相关代谢途径

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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)

23 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 15 AIMP2, ANXA5, ATF4, BCL2, BCL2L1, BRAF, CASP3, EIF4EBP1, MAPK8, MTOR, PRKAA2, SGCB, STAT3, TRAF2, XIAP
Peripheral membrane protein 4 ANXA5, CYP1B1, GORASP1, MTOR
Endoplasmic reticulum membrane 4 BCL2, CYP1B1, MTOR, NRAS
Mitochondrion membrane 1 BCL2L1
Nucleus 13 AIMP2, ATF4, BCL2, BRAF, CASP3, CD274, EIF4EBP1, MAPK8, MTOR, PARP1, PRKAA2, STAT3, XIAP
cytosol 16 AIMP2, ANXA5, ATF4, BCL2, BCL2L1, BRAF, CASP3, EIF4EBP1, MAPK8, MTOR, NRAS, PARP1, PRKAA2, STAT3, TRAF2, XIAP
dendrite 2 MTOR, PRKAA2
nuclear body 1 PARP1
phagocytic vesicle 1 MTOR
centrosome 2 ATF4, BCL2L1
nucleoplasm 10 ATF4, CASP3, CD274, MAPK8, MTOR, PARP1, PRKAA2, STAT3, TRAF2, XIAP
RNA polymerase II transcription regulator complex 2 ATF4, STAT3
Cell membrane 4 ATF4, BRAF, CD274, NRAS
Lipid-anchor 1 NRAS
Cytoplasmic side 4 BCL2L1, GORASP1, MTOR, NRAS
Early endosome membrane 1 CD274
Golgi apparatus membrane 3 GORASP1, MTOR, NRAS
Synapse 1 MAPK8
cell cortex 1 TRAF2
glutamatergic synapse 2 BRAF, CASP3
Golgi apparatus 3 GORASP1, NRAS, PRKAA2
Golgi membrane 3 GORASP1, MTOR, NRAS
lysosomal membrane 1 MTOR
mitochondrial inner membrane 1 BCL2L1
neuronal cell body 2 CASP3, PRKAA2
postsynapse 1 BRAF
sarcolemma 2 ANXA5, SGCB
Cytoplasm, cytosol 3 AIMP2, BCL2L1, PARP1
Lysosome 1 MTOR
Presynapse 1 BRAF
plasma membrane 5 BRAF, CD274, NRAS, SGCB, STAT3
synaptic vesicle membrane 1 BCL2L1
Membrane 8 AIMP2, ANXA5, BCL2, CYP1B1, MTOR, NRAS, PARP1, PRKAA2
axon 2 MAPK8, PRKAA2
extracellular exosome 3 ANXA5, CD274, NRAS
Lysosome membrane 1 MTOR
endoplasmic reticulum 2 BCL2, BCL2L1
mitochondrion 5 BCL2, BCL2L1, BRAF, CYP1B1, PARP1
protein-containing complex 4 ATF4, BCL2, PARP1, TRAF2
intracellular membrane-bounded organelle 2 BRAF, CYP1B1
Microsome membrane 2 CYP1B1, MTOR
postsynaptic density 1 CASP3
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 1 CD274
extracellular region 1 ANXA5
cytoplasmic side of plasma membrane 1 TRAF2
Mitochondrion outer membrane 3 BCL2, BCL2L1, MTOR
Single-pass membrane protein 2 BCL2, BCL2L1
mitochondrial outer membrane 3 BCL2, BCL2L1, MTOR
Mitochondrion matrix 1 BCL2L1
mitochondrial matrix 1 BCL2L1
transcription regulator complex 2 PARP1, STAT3
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 2 ATF4, BCL2L1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 BCL2L1
Nucleus membrane 2 BCL2, BCL2L1
Bcl-2 family protein complex 2 BCL2, BCL2L1
nuclear membrane 2 BCL2, BCL2L1
CD40 receptor complex 1 TRAF2
external side of plasma membrane 2 ANXA5, CD274
actin cytoskeleton 1 CD274
nucleolus 1 PARP1
Single-pass type II membrane protein 1 SGCB
Cell membrane, sarcolemma 1 SGCB
Membrane raft 1 TRAF2
pore complex 1 BCL2
Cytoplasm, cytoskeleton 1 SGCB
focal adhesion 1 ANXA5
cis-Golgi network 1 GORASP1
Nucleus, PML body 1 MTOR
PML body 1 MTOR
collagen-containing extracellular matrix 1 ANXA5
nuclear speck 2 ATF4, PRKAA2
Zymogen granule membrane 1 ANXA5
neuron projection 2 ATF4, BRAF
chromatin 3 ATF4, PARP1, STAT3
Chromosome 1 PARP1
cytoskeleton 1 SGCB
Nucleus, nucleolus 1 PARP1
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
site of double-strand break 1 PARP1
serine/threonine protein kinase complex 1 TRAF2
nuclear envelope 2 MTOR, PARP1
Recycling endosome membrane 1 CD274
Endomembrane system 1 MTOR
tertiary granule membrane 1 NRAS
cytoplasmic stress granule 1 PRKAA2
Nucleus speckle 1 ATF4
cell body 1 BRAF
myelin sheath 1 BCL2
ubiquitin ligase complex 1 TRAF2
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
vesicle membrane 2 ANXA5, TRAF2
protein-DNA complex 1 PARP1
basal dendrite 1 MAPK8
death-inducing signaling complex 1 CASP3
[Isoform 1]: Cell membrane 1 CD274
[Isoform 4]: Secreted 1 CD274
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
dendrite membrane 1 ATF4
dystrophin-associated glycoprotein complex 1 SGCB
sarcoglycan complex 1 SGCB
nucleotide-activated protein kinase complex 1 PRKAA2
Cytoplasmic vesicle, phagosome 1 MTOR
site of DNA damage 1 PARP1
IRE1-TRAF2-ASK1 complex 1 TRAF2
nuclear periphery 1 ATF4
endothelial microparticle 1 ANXA5
TRAF2-GSTP1 complex 1 TRAF2
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
BAD-BCL-2 complex 1 BCL2
ATF4-CREB1 transcription factor complex 1 ATF4
ATF1-ATF4 transcription factor complex 1 ATF4
CHOP-ATF4 complex 1 ATF4
Lewy body core 1 ATF4
tumor necrosis factor receptor superfamily complex 1 TRAF2
[Isoform Bcl-X(L)]: Mitochondrion inner membrane 1 BCL2L1
[Isoform 2]: Endomembrane system 1 CD274


文献列表

  • Weijia Yang, Minchun Yang, Hui Yao, Yelin Ma, Xuanxuan Ren, Long Teng, Tao Wang. Protective role of arnebin-1 in rats with nonalcoholic fatty liver disease. The Journal of international medical research. 2019 Mar; 47(3):1250-1263. doi: 10.1177/0300060518813058. [PMID: 30678506]
  • Zohreh Jahanafrooz, Alexander Stallinger, Ines Anders, Florian Kleinegger, Birgit Lohberger, Christin Durchschein, Rudolf Bauer, Alexander Deutsch, Beate Rinner, Nadine Kretschmer. Influence of silibinin and β-β-dimethylacrylshikonin on chordoma cells. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2018 Oct; 49(?):32-40. doi: 10.1016/j.phymed.2018.06.005. [PMID: 30217260]
  • Sukanya Pandeti, Deepti Arha, Akansha Mishra, Sabbu Sathish Reddy, Arvind K Srivastava, Tadigoppula Narender, Akhilesh K Tamrakar. Glucose uptake stimulatory potential and antidiabetic activity of the Arnebin-1 from Arnabia nobelis. European journal of pharmacology. 2016 Oct; 789(?):449-457. doi: 10.1016/j.ejphar.2016.08.010. [PMID: 27521155]
  • Hai-bing Wang, Xiao-qiong Ma. β, β-Dimethylacrylshikonin induces mitochondria-dependent apoptosis of human lung adenocarcinoma cells in vitro via p38 pathway activation. Acta pharmacologica Sinica. 2015 Jan; 36(1):131-8. doi: 10.1038/aps.2014.108. [PMID: 25434989]
  • Zhi Zeng, Bang-Hao Zhu. Arnebin-1 promotes the angiogenesis of human umbilical vein endothelial cells and accelerates the wound healing process in diabetic rats. Journal of ethnopharmacology. 2014 Jul; 154(3):653-62. doi: 10.1016/j.jep.2014.04.038. [PMID: 24794013]
  • Nadine Kretschmer, Beate Rinner, Alexander J A Deutsch, Birgit Lohberger, Heike Knausz, Olaf Kunert, Martina Blunder, Herbert Boechzelt, Helmut Schaider, Rudolf Bauer. Naphthoquinones from Onosma paniculata induce cell-cycle arrest and apoptosis in melanoma Cells. Journal of natural products. 2012 May; 75(5):865-9. doi: 10.1021/np2006499. [PMID: 22530779]
  • Xiu-Jin Shen, Hai-Bing Wang, Xiao-Qiong Ma, Jiang-Hua Chen. β,β-Dimethylacrylshikonin induces mitochondria dependent apoptosis through ERK pathway in human gastric cancer SGC-7901 cells. PloS one. 2012; 7(7):e41773. doi: 10.1371/journal.pone.0041773. [PMID: 22848597]
  • Yingying Fan, Shaoju Jin, Jun He, Zhenjun Shao, Jiao Yan, Ting Feng, Hong Li. Effect of β,β-dimethylacrylshikonin on inhibition of human colorectal cancer cell growth in vitro and in vivo. International journal of molecular sciences. 2012; 13(7):9184-9193. doi: 10.3390/ijms13079184. [PMID: 22942759]
  • T Kundakovic, N Fokialakis, S Dobric, H Pratsinis, D Kletsas, N Kovacevic, I Chinou. Evaluation of the anti-inflammatory and cytotoxic activities of naphthazarine derivatives from Onosma leptantha. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2006 Mar; 13(4):290-4. doi: 10.1016/j.phymed.2004.10.009. [PMID: 16492534]
  • B Z Ahn, K U Baik, G R Kweon, K Lim, B D Hwang. Acylshikonin analogues: synthesis and inhibition of DNA topoisomerase-I. Journal of medicinal chemistry. 1995 Mar; 38(6):1044-7. doi: 10.1021/jm00006a025. [PMID: 7699697]
  • S Wahab, R N Tandon, Z Jacob, B Chandra, O P Srivastava. Comparative in vitro and in vivo effect of lactones and arnebins on Trichophyton mentagrophytes and Candida albicans. The Indian journal of medical research. 1982 Dec; 76 Suppl(?):77-82. doi: ". [PMID: 6764457]