4'-Demethylepipodophyllotoxin (BioDeep_00000000526)

 

Secondary id: BioDeep_00000600165

PANOMIX_OTCML-2023


代谢物信息卡片


(5S,5aR,8aR,9R)-5-hydroxy-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one

化学式: C21H20O8 (400.1158)
中文名称: 4'-去甲基表鬼臼毒素, 4-去甲基表鬼臼毒素
谱图信息: 最多检出来源 Viridiplantae(plant) 17.28%

Reviewed

Last reviewed on 2024-08-14.

Cite this Page

4'-Demethylepipodophyllotoxin. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/4_-demethylepipodophyllotoxin (retrieved 2024-12-22) (BioDeep RN: BioDeep_00000000526). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: COC1=CC(=CC(=C1O)OC)C2C3C(COC3=O)C(C4=CC5=C(C=C24)OCO5)O
InChI: InChI=1S/C21H20O8/c1-25-15-3-9(4-16(26-2)20(15)23)17-10-5-13-14(29-8-28-13)6-11(10)19(22)12-7-27-21(24)18(12)17/h3-6,12,17-19,22-23H,7-8H2,1-2H3/t12-,17+,18-,19+/m0/s1

描述信息

4-demethylepipodophyllotoxin is an organic heterotetracyclic compound that is the 9- epimer of 4-demethylpodophyllotoxin. It has a role as an antineoplastic agent. It is a furonaphthodioxole, an organic heterotetracyclic compound and a member of phenols.
An organic heterotetracyclic compound that is the 9- epimer of 4-demethylpodophyllotoxin.
4'-Demethylepipodophyllotoxin (4'-DMEP) is an intermediate compound that inhibits microtubule assembly.
4'-Demethylepipodophyllotoxin (4'-DMEP) is an intermediate compound that inhibits microtubule assembly.

同义名列表

37 个代谢物同义名

Furo(3,4:6,7)naphtho(2,3-d)-1,3-dioxol-6(5ah)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R-(5-alpha,5a-beta,8a-alpha,9-beta))-; (5R-(5alpha,5abeta,8aalpha,9beta))-5,8,8a,9-Tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-furo(3,4:6,7)naphtho(2,3-d)-1,3-dioxol-6(5aH)-one; (10R,11R,15R,16S)-16-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.0^{3,7}.0^{11,15}]hexadeca-1,3(7),8-trien-12-one; (10R,11R,15R,16S)-16-hydroxy-10-(4-hydroxy-3,5-dimethoxyphenyl)-4,6,13-trioxatetracyclo[7.7.0.03,7.011,15]hexadeca-1,3(7),8-trien-12-one; FURO(3,4:6,7)NAPHTHO(2,3-D)-1,3-DIOXOL-6(5AH)-ONE, 5,8,8A,9-TETRAHYDRO-9-HYDROXY-5-(4-HYDROXY-3,5-DIMETHOXYPHENYL)-, (5R,5AR,8AR,9S)-; Furo[3,4:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-, (5R,5aR,8aR,9S)-; (5R,5aR,8aR,9S)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-furo[3,4:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one; (5R,5aR,8aR,9S)-5,8,8a,9-tetrahydro-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)furo[3,4:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one; (5R,5aR,8aR,9S)-9-hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3,4:6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-one; (5s,5ar,8ar,9r)-9-(3,5-Dimethoxy-4-Oxidanyl-Phenyl)-5-Oxidanyl-5a,6,8a,9-Tetrahydro-5h-[2]benzofuro[6,5-F][1,3]benzodioxol-8-One; (5R,5aR,8aR,9S)-9-Hydroxy-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3,4:6,7]naphtho[2,3-d][1,3]dioxol-6(5aH)-on; (5S,5aR,8aR,9R)-5-hydroxy-9-(4-hydroxy-3,5-dimethoxy-phenyl)-5a,6,8a,9-tetrahydro-5H-isobenzofuro[6,5-f][1,3]benzodioxol-8-one; 4-Demethylepipodophyllotoxin; Teniposide Related Compound A; Etoposide Impurity E; Podophyllotoxin Impurity B; 4-O-demethylepipodophyllotoxin;4-DMEP; (-)-4-demethyl-epipodophyllotoxin; 4'-Demethylepipodophyllotoxin; 4-O-demethyl-4-epipodophyllotoxin; (-)-4-Demethylepipodophyllotoxin; 4-demethyl-9-epipodophyllotoxin; Epipodophyllotoxin, 4-demethyl-; 4-O-demethylepipodophyllotoxin; 4-demethyl epipodophyllotoxin; 4-Demethyl-epipodophyllotoxin; epi-4-demethylpodophyllotoxin; 4-Demethylepipodophyllotoxin; Demethylpodophyllotoxin, 4-; YVCVYCSAAZQOJI-JHQYFNNDSA-N; etoposide aglycone; UNII-X0S6I23X6L; Tox21_113196; X0S6I23X6L; 4-DMEP; DMEP; 89O; 4'-O-demethylepipodophyllotoxin; 4'-DMEP; 4'-Demethylepipodophyllotoxin



数据库引用编号

10 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)

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 14 ABCB1, AXIN2, BCL2, CASP3, CAT, GTPBP1, HMGB1, HPRT1, MDM2, PARK7, PIK3CA, RPL11, SGCB, TUBB4B
Peripheral membrane protein 1 HMGB1
Endoplasmic reticulum membrane 1 BCL2
Nucleus 9 ADK, AXIN2, BCL2, CASP3, HMGB1, MDM2, PARK7, TOP1, TUBB4B
cytosol 14 ADK, AXIN2, BCL2, CASP3, CAT, GTPBP1, HPRT1, MDM2, PARK7, PIK3CA, PRKCQ, RPL11, TNNT2, TUBB4B
centrosome 1 AXIN2
nucleoplasm 8 ADK, CASP3, CD2, HMGB1, MDM2, PARK7, RPL11, TOP1
Cell membrane 4 ABCB1, CD2, HMGB1, PARK7
Lipid-anchor 1 PARK7
lamellipodium 1 PIK3CA
Multi-pass membrane protein 2 ABCB1, TM2D1
cell surface 3 ABCB1, CD2, HMGB1
glutamatergic synapse 2 CASP3, MDM2
Golgi apparatus 1 CD2
neuronal cell body 1 CASP3
sarcolemma 1 SGCB
synaptic vesicle 1 PARK7
endosome 1 HMGB1
plasma membrane 11 ABCB1, ADK, AXIN2, CD2, HMGB1, MDM2, PARK7, PIK3CA, PRKCQ, SGCB, TM2D1
Membrane 7 ABCB1, BCL2, CAT, GTPBP1, PARK7, RPL11, TM2D1
apical plasma membrane 1 ABCB1
axon 1 PARK7
extracellular exosome 6 ABCB1, CAT, HPRT1, PARK7, RPL11, TUBB4B
endoplasmic reticulum 3 BCL2, HMGB1, PARK7
extracellular space 1 HMGB1
perinuclear region of cytoplasm 2 PARK7, PIK3CA
adherens junction 1 PARK7
intercalated disc 1 PIK3CA
mitochondrion 3 BCL2, CAT, PARK7
protein-containing complex 5 BCL2, CAT, CD2, MDM2, RPL11
intracellular membrane-bounded organelle 1 CAT
postsynaptic density 2 CASP3, MDM2
Single-pass type I membrane protein 1 CD2
Secreted 1 HMGB1
extracellular region 4 CAT, CD2, HMGB1, TUBB4B
cytoplasmic side of plasma membrane 1 CD2
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 1 BCL2
mitochondrial outer membrane 1 BCL2
mitochondrial matrix 2 CAT, PARK7
Extracellular side 1 HMGB1
centriolar satellite 1 PRKCQ
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 CD2
Extracellular vesicle 1 TUBB4B
perikaryon 1 TOP1
beta-catenin destruction complex 1 AXIN2
microtubule cytoskeleton 1 TUBB4B
nucleolus 3 MDM2, RPL11, TOP1
P-body 1 TOP1
cell-cell junction 1 CD2
Single-pass type II membrane protein 1 SGCB
Apical cell membrane 1 ABCB1
Cell membrane, sarcolemma 1 SGCB
Membrane raft 1 PARK7
pore complex 1 BCL2
Cytoplasm, cytoskeleton 2 SGCB, TUBB4B
focal adhesion 1 CAT
microtubule 1 TUBB4B
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
PML body 1 PARK7
mitochondrial intermembrane space 1 PARK7
sarcomere 1 TNNT2
chromatin 1 PARK7
mitotic spindle 1 TUBB4B
Chromosome 2 HMGB1, TOP1
cytoskeleton 2 SGCB, TUBB4B
Nucleus, nucleolus 3 MDM2, RPL11, TOP1
intercellular bridge 1 TUBB4B
Cytoplasm, cytoskeleton, flagellum axoneme 1 TUBB4B
sperm flagellum 1 TUBB4B
fibrillar center 1 TOP1
axonemal microtubule 1 TUBB4B
Nucleus, nucleoplasm 2 MDM2, TOP1
cell body 1 PARK7
myelin sheath 1 BCL2
cytoplasmic exosome (RNase complex) 1 GTPBP1
ficolin-1-rich granule lumen 2 CAT, HMGB1
secretory granule lumen 2 CAT, HMGB1
transcription repressor complex 2 HMGB1, MDM2
male germ cell nucleus 1 TOP1
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
endocytic vesicle membrane 1 MDM2
azurophil granule lumen 1 TUBB4B
immunological synapse 1 PRKCQ
aggresome 1 PRKCQ
[Isoform 2]: Cytoplasm 1 ADK
ribonucleoprotein complex 1 RPL11
endoplasmic reticulum-Golgi intermediate compartment 1 HMGB1
[Isoform 1]: Nucleus 1 ADK
protein-DNA complex 1 TOP1
external side of apical plasma membrane 1 ABCB1
death-inducing signaling complex 1 CASP3
dystrophin-associated glycoprotein complex 1 SGCB
sarcoglycan complex 1 SGCB
condensed chromosome 1 HMGB1
cytosolic ribosome 1 RPL11
ribosome 1 RPL11
cardiac myofibril 1 TNNT2
troponin complex 1 TNNT2
catalase complex 1 CAT
alphav-beta3 integrin-HMGB1 complex 1 HMGB1
cytosolic large ribosomal subunit 1 RPL11
BAD-BCL-2 complex 1 BCL2
cardiac Troponin complex 1 TNNT2
striated muscle thin filament 1 TNNT2
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA


文献列表

  • Shenghu Guo, Yuchao Chen, Yongxing Zhu, Mei Tian. Transcriptome analysis reveals differentially expressed genes involved in somatic embryogenesis and podophyllotoxin biosynthesis of Sinopodophyllum hexandrum (Royle) T. S. Ying. Protoplasma. 2023 Feb; ?(?):. doi: 10.1007/s00709-023-01843-9. [PMID: 36840780]
  • Jian-Long Li, Wei Zhao, Chen Zhou, Ya-Xuan Zhang, Hong-Mei Li, Ya-Ling Tang, Xin-Hua Liang, Tao Chen, Ya-Jie Tang. Comparison of carbon-sulfur and carbon-amine bond in therapeutic drug: 4β-S-aromatic heterocyclic podophyllum derivatives display antitumor activity. Scientific reports. 2015 Oct; 5(?):14814. doi: 10.1038/srep14814. [PMID: 26443888]
  • Warren Lau, Elizabeth S Sattely. Six enzymes from mayapple that complete the biosynthetic pathway to the etoposide aglycone. Science (New York, N.Y.). 2015 Sep; 349(6253):1224-8. doi: 10.1126/science.aac7202. [PMID: 26359402]
  • Xiao-Yu Zhang, Wen-Guang Li, Yong-Jie Wu, Xuan Tian. Antioxidative and antitumor activity of derivatives of 4-beta-amino-4'-demethylepipodophyllotoxin and their structure-activity relationship. Die Pharmazie. 2007 Jun; 62(6):432-8. doi: . [PMID: 17663190]
  • J H Holmes, I Kanfer, H Zwarenstein. Effect of benzodiazepine derivatives on human blood cholinesterase in vitro. Research communications in chemical pathology and pharmacology. 1978 Aug; 21(2):367-70. doi: . [PMID: 29327]