ARNEBIN-7 (BioDeep_00000000479)

   

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


5,8-dihydroxy-2-(4-methylpent-3-en-1-yl)-1,4-dihydronaphthalene-1,4-dione

化学式: C16H16O4 (272.1049)
中文名称: 去氧紫草素, 去氧紫根素
谱图信息: 最多检出来源 Viridiplantae(plant) 19.51%

分子结构信息

SMILES: CC(=CCCC1=CC(=O)C2=C(C=CC(=C2C1=O)O)O)C
InChI: InChI=1S/C16H16O4/c1-9(2)4-3-5-10-8-13(19)14-11(17)6-7-12(18)15(14)16(10)20/h4,6-8,17-18H,3,5H2,1-2H3

描述信息

Deoxyshikonin is a hydroxy-1,4-naphthoquinone.
Deoxyshikonin is a natural product found in Arnebia hispidissima, Alkanna cappadocica, and other organisms with data available.
See also: Arnebia guttata root (part of); Arnebia euchroma root (part of); Lithospermum erythrorhizon root (part of).
Deoxyshikonin is isolated from Arnebia euchroma with antitumor activity. Deoxyshikonin increases the expression of VEGF-C and VEGF-A mRNA in HMVEC-dLy, promotes HIF-1α and HIF-1β subunit interaction and binds to specific DNA sequences targeted by HIF, indicates a prolymphangiogenesis as well as a proangiogenesis effect in vitro[1]. Deoxyshikonin shows significant synergic antimicrobial activity against S. pneumonia (MIC=17 μg/mL), also shows significantly inhibitory activities against MRSA[2].
Deoxyshikonin increases the expression of VEGF-C and VEGF-A mRNA in HMVEC-dLy, promotes HIF-1α and HIF-1β subunit interaction and binds to specific DNA sequences targeted by HIF. Deoxyshikonin inhibited colorectal cancer (CRC) through the PI3K/Akt/mTOR pathway. Deoxyshikonin has proangiogenesis effect and antitumor activity. Deoxyshikonin is an antibacterial agent against methicillin-resistant S. aureus (MRSA) and S. pneumonia (MIC=17 μg/mL)[1][2][3].
Deoxyshikonin is isolated from Arnebia euchroma with antitumor activity. Deoxyshikonin increases the expression of VEGF-C and VEGF-A mRNA in HMVEC-dLy, promotes HIF-1α and HIF-1β subunit interaction and binds to specific DNA sequences targeted by HIF, indicates a prolymphangiogenesis as well as a proangiogenesis effect in vitro[1]. Deoxyshikonin shows significant synergic antimicrobial activity against S. pneumonia (MIC=17 μg/mL), also shows significantly inhibitory activities against MRSA[2].

同义名列表

16 个代谢物同义名

1,4-Naphthalenedione, 5,8-dihydroxy-2-(4-methyl-3-pentenyl)-; 5,8-dihydroxy-2-(4-methylpent-3-enyl)naphthalene-1,4-dione; 5,8-dihydroxy-2-(4-methylpent-3-enyl)-1,4-naphthoquinone; 5,8-Dihydroxy-2-(4-methyl-3-pentenyl)naphthoquinone; Deoxyshikonin; NSC 179184; 43043-74-9; ARNEBIN-7; Arnebin 7; NSC179184; 5,8-dihydroxy-2-(4-methylpent-3-en-1-yl)-1,4-dihydronaphthalene-1,4-dione; 1,4-Naphthalenedione,5,8-dihydroxy-2-(4-methyl-3-penten-1-yl)-; Arnebin VII;Deoxyalkannin;Anhydroalkanin;Arnebin 7;NSC 179184; 5,8-Dihydroxy-2-(4-methyl-3-pentenyl)-1,4-naphthalenedione; 5,8-Dihydroxy-2-(4-methyl-3-pentenyl)naphthoquinone #; VOMDIEGPEURZJO-UHFFFAOYSA-N



数据库引用编号

13 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

2 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(1)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(1)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

36 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 ABCB1, AIMP2, ANG, CASP3, CASP7, CASP9, CYP2B6, FOXO1, HIF1A, MTOR, NOL3, PIK3CA, PKM, SIRT1, XIAP
Peripheral membrane protein 3 CYP1B1, CYP2B6, MTOR
Endoplasmic reticulum membrane 5 CYP1A2, CYP1B1, CYP2B6, HMOX1, MTOR
Nucleus 13 AIMP2, ANG, CASP3, CASP7, CASP9, FOXO1, HIF1A, HMOX1, KDR, MTOR, PKM, SIRT1, XIAP
cytosol 14 AIMP2, ANG, CASP3, CASP7, CASP9, FOXO1, HIF1A, HMOX1, MTOR, NOL3, PIK3CA, PKM, SIRT1, XIAP
dendrite 1 MTOR
nuclear body 1 HIF1A
phagocytic vesicle 1 MTOR
nucleoplasm 8 CASP3, CASP7, FOXO1, HIF1A, HMOX1, MTOR, SIRT1, XIAP
RNA polymerase II transcription regulator complex 1 HIF1A
Cell membrane 2 ABCB1, KDR
Lipid-anchor 1 NOL3
Cytoplasmic side 2 HMOX1, MTOR
lamellipodium 1 PIK3CA
Multi-pass membrane protein 1 ABCB1
Golgi apparatus membrane 1 MTOR
cell junction 1 KDR
cell surface 1 ABCB1
glutamatergic synapse 1 CASP3
Golgi apparatus 1 KDR
Golgi membrane 1 MTOR
growth cone 1 ANG
lysosomal membrane 1 MTOR
neuronal cell body 2 ANG, CASP3
Cytoplasm, cytosol 2 AIMP2, CASP7
Lysosome 1 MTOR
endosome 1 KDR
plasma membrane 3 ABCB1, KDR, PIK3CA
Membrane 6 ABCB1, AIMP2, CYP1B1, HMOX1, MTOR, NOL3
apical plasma membrane 1 ABCB1
axon 1 CCK
extracellular exosome 2 ABCB1, PKM
Lysosome membrane 1 MTOR
endoplasmic reticulum 2 HMOX1, KDR
extracellular space 4 ANG, CASP7, CCK, HMOX1
perinuclear region of cytoplasm 2 HMOX1, PIK3CA
intercalated disc 1 PIK3CA
mitochondrion 6 CASP9, CYP1B1, FOXO1, NOL3, PKM, SIRT1
protein-containing complex 2 CASP9, HIF1A
intracellular membrane-bounded organelle 3 CYP1A2, CYP1B1, CYP2B6
Microsome membrane 4 CYP1A2, CYP1B1, CYP2B6, MTOR
postsynaptic density 1 CASP3
chromatin silencing complex 1 SIRT1
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Secreted 2 ANG, CCK
extracellular region 4 ANG, CCK, KDR, PKM
Mitochondrion outer membrane 1 MTOR
mitochondrial outer membrane 2 HMOX1, MTOR
[Isoform 2]: Secreted 1 KDR
anchoring junction 1 KDR
motile cilium 1 HIF1A
external side of plasma membrane 1 KDR
Extracellular vesicle 1 PKM
actin cytoskeleton 1 ANG
nucleolus 3 ANG, NOL3, SIRT1
axon cytoplasm 1 HIF1A
sarcoplasm 1 NOL3
Early endosome 1 KDR
vesicle 1 PKM
Apical cell membrane 1 ABCB1
heterochromatin 1 SIRT1
Membrane raft 1 KDR
basement membrane 1 ANG
sarcoplasmic reticulum 1 NOL3
Nucleus, PML body 2 MTOR, SIRT1
PML body 2 MTOR, SIRT1
collagen-containing extracellular matrix 1 PKM
nuclear speck 1 HIF1A
nuclear inner membrane 1 SIRT1
receptor complex 1 KDR
cilium 1 PKM
chromatin 3 FOXO1, HIF1A, SIRT1
Chromosome 1 ANG
Secreted, extracellular space 1 CASP7
Nucleus, nucleolus 1 ANG
fibrillar center 1 SIRT1
nuclear envelope 2 MTOR, SIRT1
Endomembrane system 1 MTOR
sorting endosome 1 KDR
Cytoplasm, Stress granule 1 ANG
cytoplasmic stress granule 1 ANG
Nucleus speckle 1 HIF1A
euchromatin 2 HIF1A, SIRT1
[Isoform 3]: Cytoplasm 1 NOL3
ficolin-1-rich granule lumen 1 PKM
secretory granule lumen 1 PKM
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
endocytic vesicle 1 ANG
Single-pass type IV membrane protein 1 HMOX1
apoptosome 1 CASP9
[Isoform 2]: Cytoplasm 1 NOL3
[Isoform 1]: Nucleus, nucleolus 1 NOL3
external side of apical plasma membrane 1 ABCB1
death-inducing signaling complex 1 CASP3
eNoSc complex 1 SIRT1
rDNA heterochromatin 1 SIRT1
aminoacyl-tRNA synthetase multienzyme complex 1 AIMP2
Rough endoplasmic reticulum 1 PKM
Cytoplasmic vesicle, phagosome 1 MTOR
angiogenin-PRI complex 1 ANG
[Isoform M2]: Cytoplasm 1 PKM
[Isoform M1]: Cytoplasm 1 PKM
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
caspase complex 1 CASP9
[SirtT1 75 kDa fragment]: Cytoplasm 1 SIRT1


文献列表

  • Kamil Wierzchowski, Bartosz Nowak, Mateusz Kawka, Patryk Więckowicz, Katarzyna Dąbkowska-Susfał, Agnieszka Pietrosiuk, Katarzyna Sykłowska-Baranek, Maciej Pilarek. Selective Impact of MTMS-Based Xerogel Morphology on Boosted Proliferation and Enhanced Naphthoquinone Production in Cultures of Rindera graeca Transgenic Roots. International journal of molecular sciences. 2022 Nov; 23(22):. doi: 10.3390/ijms232213669. [PMID: 36430149]
  • Wan Song, Yibin Zhuang, Tao Liu. CYP82AR Subfamily Proteins Catalyze C-1' Hydroxylations of Deoxyshikonin in the Biosynthesis of Shikonin and Alkannin. Organic letters. 2021 04; 23(7):2455-2459. doi: 10.1021/acs.orglett.1c00360. [PMID: 33728922]
  • Jun Yeon Park, Myoung-Sook Shin, Gwi Seo Hwang, Noriko Yamabe, Jeong-Eun Yoo, Ki Sung Kang, Jin-Chul Kim, Jeong Gun Lee, Jungyeob Ham, Hye Lim Lee. Beneficial Effects of Deoxyshikonin on Delayed Wound Healing in Diabetic Mice. International journal of molecular sciences. 2018 Nov; 19(11):. doi: 10.3390/ijms19113660. [PMID: 30463303]
  • Alexandra G Durán, M Teresa Gutiérrez, Carlos Rial, Ascensión Torres, Rosa M Varela, Manuel M Valdivia, José M G Molinillo, Dominik Skoneczny, Leslie A Weston, Francisco A Macías. Bioactivity and quantitative analysis of isohexenylnaphthazarins in root periderm of two Echium spp.: E. plantagineum and E. gaditanum. Phytochemistry. 2017 Sep; 141(?):162-170. doi: 10.1016/j.phytochem.2017.06.004. [PMID: 28633108]
  • Jun Yeon Park, Jin Ho Kwak, Ki Sung Kang, Eun Bee Jung, Dong-Soo Lee, Sanghyun Lee, Yujung Jung, Ki Hyun Kim, Gwi Seo Hwang, Hye Lim Lee, Noriko Yamabe, Su-Nam Kim. Wound healing effects of deoxyshikonin isolated from Jawoongo: In vitro and in vivo studies. Journal of ethnopharmacology. 2017 Mar; 199(?):128-137. doi: 10.1016/j.jep.2016.10.031. [PMID: 27725239]