Dihydrocucurbitacin B (BioDeep_00000000573)

 

Secondary id: BioDeep_00000865179

PANOMIX_OTCML-2023 natural product


代谢物信息卡片


[(6R)-6-[(2S,8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxoheptan-2-yl] acetate

化学式: C32H48O8 (560.3349)
中文名称: 二氢葫芦素 B, 二氢葫芦素B
谱图信息: 最多检出来源 Homo sapiens(otcml) 7.42%

分子结构信息

SMILES: CC(=O)OC(C)(C)CCC(=O)C(C)(C1C(CC2(C1(CC(=O)C3(C2CC=C4C3CC(C(=O)C4(C)C)O)C)C)C)O)O
InChI: InChI=1S/C32H48O8/c1-17(33)40-27(2,3)13-12-23(36)32(9,39)25-21(35)15-29(6)22-11-10-18-19(14-20(34)26(38)28(18,4)5)31(22,8)24(37)16-30(25,29)7/h10,19-22,25,34-35,39H,11-16H2,1-9H3/t19-,20+,21-,22+,25+,29+,30-,31+,32+/m1/s1

描述信息

23,24-dihydrocucurbitacin B is a 23,24-dihydrocucurbitacin in which a lanostane skeleton is multi-substituted with hydroxy, methyl and oxo substituents, with unsaturation at position 5; a hydroxy function at C-25 is acetylated. It is a 23,24-dihydrocucurbitacin, a secondary alpha-hydroxy ketone and a tertiary alpha-hydroxy ketone. It is functionally related to a cucurbitacin B.
Dihydrocucurbitacin B is a natural product found in Bryonia alba, Citrullus colocynthis, and other organisms with data available.
Dihydrocucurbitacin B, a triterpene isolated from Cayaponia tayuya roots, inhibits nuclear factor of activated T cells (NFAT), induces cell cycle arrested in the G0 phase, and inhibits delayed type hypersensitivity[1].
Dihydrocucurbitacin B, a triterpene isolated from Cayaponia tayuya roots, inhibits nuclear factor of activated T cells (NFAT), induces cell cycle arrested in the G0 phase, and inhibits delayed type hypersensitivity[1].

同义名列表

11 个代谢物同义名

[(6R)-6-[(2S,8S,9R,10R,13R,14S,16R,17R)-2,16-dihydroxy-4,4,9,13,14-pentamethyl-3,11-dioxo-2,7,8,10,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-2-methyl-5-oxoheptan-2-yl] acetate; 19-NORLANOST-5-ENE-3,11,22-TRIONE, 25-(ACETYLOXY)-2,16,20-TRIHYDROXY-9-METHYL-, (2.BETA.,9.BETA.,10.ALPHA.,16.ALPHA.)-; (2.BETA.,9.BETA.,10.ALPHA.,16.ALPHA.)-25-(ACETYLOXY)-2,16,20-TRIHYDROXY-9-METHYL-19-NORLANOST-5-ENE-3,11,22-TRIONE; (2S,4R)-2,16beta,20-trihydroxy-9beta,10,14-trimethyl-1,11,22-trioxo-4,9-cyclo-9,10-secocholest-5-en-25-yl acetate; 2beta,16alpha,20,25-tetrahydroxy-9-methyl-3,11,22-trioxo-19-nor-9beta,10alpha-lanost-5-en-25-yl acetate; 2beta,16alpha,20,25-tetrahydroxy-9-methyl-19-nor-9beta,10alpha-lanost-5-ene-3,11,22-trione, 25-acetate; (10alpha)-25-(Acetyloxy)-2beta,16alpha,20-trihydroxy-9beta-methyl-19-norlanost-5-ene-3,11,22-trione; 25-acetoxy-2beta,16alpha,20-trihydroxy-10alpha-cucurbit-5-ene-3,11,22-trione; 23,24-dihydrocucurbitacin B; Cucurbitacin B, dihydro-; Dihydrocucurbitacin B



数据库引用编号

12 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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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)

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 12 ANXA5, CCNB1, ELANE, MTOR, NOS2, PCSK9, PHB2, PIK3CA, PTGS1, PTGS2, SREBF2, STAT3
Peripheral membrane protein 4 ANXA5, MTOR, PTGS1, PTGS2
Endosome membrane 1 LDLR
Endoplasmic reticulum membrane 4 MTOR, PTGS1, PTGS2, SREBF2
Nucleus 6 CCNB1, MTOR, NOS2, PHB2, SREBF2, STAT3
cytosol 9 ANXA5, CCNB1, ELANE, IL1B, MTOR, NOS2, PIK3CA, SREBF2, STAT3
dendrite 1 MTOR
phagocytic vesicle 2 ELANE, MTOR
centrosome 1 CCNB1
nucleoplasm 5 CCNB1, MTOR, NOS2, SREBF2, STAT3
RNA polymerase II transcription regulator complex 1 STAT3
Cell membrane 2 LDLR, PHB2
Cytoplasmic side 1 MTOR
lamellipodium 1 PIK3CA
Multi-pass membrane protein 1 SREBF2
Golgi apparatus membrane 2 MTOR, SREBF2
cell surface 4 ELANE, LDLR, PCSK9, PHB2
glutamatergic synapse 1 PHB2
Golgi apparatus 3 LDLR, PCSK9, PTGS1
Golgi membrane 2 MTOR, SREBF2
lysosomal membrane 2 MTOR, PCSK9
mitochondrial inner membrane 1 PHB2
sarcolemma 1 ANXA5
Cytoplasm, cytosol 2 IL1B, NOS2
Lysosome 4 IL1B, LDLR, MTOR, PCSK9
endosome 1 PCSK9
plasma membrane 8 IFNLR1, LDLR, LTB, NOS2, PCSK9, PHB2, PIK3CA, STAT3
presynaptic active zone 1 PHB2
Membrane 7 ANXA5, CCNB1, IFNLR1, LDLR, LTB, MTOR, PHB2
axon 1 PHB2
basolateral plasma membrane 1 LDLR
caveola 1 PTGS2
extracellular exosome 3 ANXA5, ELANE, PTGS1
Lysosome membrane 1 MTOR
endoplasmic reticulum 3 PCSK9, PTGS2, SREBF2
extracellular space 7 ELANE, IL10, IL1B, IL2, IL4, LTB, PCSK9
perinuclear region of cytoplasm 3 NOS2, PCSK9, PIK3CA
intercalated disc 1 PIK3CA
mitochondrion 1 PHB2
protein-containing complex 2 PHB2, PTGS2
intracellular membrane-bounded organelle 2 PTGS1, SREBF2
Microsome membrane 3 MTOR, PTGS1, PTGS2
postsynaptic density 1 PHB2
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 2 IFNLR1, LDLR
Secreted 5 IL10, IL1B, IL2, IL4, PCSK9
extracellular region 7 ANXA5, ELANE, IL10, IL1B, IL2, IL4, PCSK9
Mitochondrion outer membrane 1 MTOR
Single-pass membrane protein 1 LDLR
mitochondrial outer membrane 2 MTOR, PHB2
mitochondrial matrix 1 CCNB1
transcription regulator complex 1 STAT3
photoreceptor outer segment 1 PTGS1
external side of plasma membrane 2 ANXA5, LDLR
low-density lipoprotein particle 1 LDLR
Cytoplasm, P-body 1 NOS2
P-body 1 NOS2
Early endosome 2 LDLR, PCSK9
Membrane, clathrin-coated pit 1 LDLR
apical part of cell 1 LDLR
clathrin-coated pit 1 LDLR
COPII-coated ER to Golgi transport vesicle 1 PCSK9
Single-pass type II membrane protein 1 LTB
Cytoplasm, perinuclear region 1 NOS2
Mitochondrion inner membrane 1 PHB2
focal adhesion 1 ANXA5
GABA-ergic synapse 1 PHB2
Peroxisome 1 NOS2
peroxisomal matrix 1 NOS2
Nucleus, PML body 1 MTOR
PML body 1 MTOR
collagen-containing extracellular matrix 2 ANXA5, ELANE
secretory granule 2 ELANE, IL1B
Nucleus inner membrane 1 PTGS2
Nucleus outer membrane 1 PTGS2
nuclear inner membrane 1 PTGS2
nuclear outer membrane 1 PTGS2
Late endosome 2 LDLR, PCSK9
receptor complex 1 LDLR
Zymogen granule membrane 1 ANXA5
neuron projection 2 PTGS1, PTGS2
chromatin 2 SREBF2, STAT3
cell periphery 1 PHB2
spindle pole 1 CCNB1
nuclear envelope 1 MTOR
Endomembrane system 3 LDLR, MTOR, PTGS1
sorting endosome 1 LDLR
endoplasmic reticulum lumen 2 PCSK9, PTGS2
nuclear matrix 1 PHB2
transcription repressor complex 1 ELANE
phosphatidylinositol 3-kinase complex 1 PIK3CA
phosphatidylinositol 3-kinase complex, class IA 1 PIK3CA
specific granule lumen 1 ELANE
Secreted, extracellular exosome 1 IL1B
azurophil granule lumen 1 ELANE
ER to Golgi transport vesicle membrane 1 SREBF2
outer kinetochore 1 CCNB1
vesicle membrane 1 ANXA5
clathrin-coated endocytic vesicle membrane 1 LDLR
endolysosome membrane 2 LDLR, PCSK9
SREBP-SCAP-Insig complex 1 SREBF2
somatodendritic compartment 1 LDLR
Cytoplasmic vesicle, phagosome 2 ELANE, MTOR
extrinsic component of external side of plasma membrane 1 PCSK9
Cytoplasmic vesicle, COPII-coated vesicle membrane 1 SREBF2
PCSK9-LDLR complex 2 LDLR, PCSK9
cortical cytoskeleton 1 NOS2
cyclin B1-CDK1 complex 1 CCNB1
PCSK9-AnxA2 complex 1 PCSK9
endothelial microparticle 1 ANXA5
mitochondrial prohibitin complex 1 PHB2
phosphatidylinositol 3-kinase complex, class IB 1 PIK3CA
[Isoform 2]: Mitochondrion inner membrane 1 PHB2
[Isoform 1]: Mitochondrion inner membrane 1 PHB2
interleukin-28 receptor complex 1 IFNLR1
[Sterol regulatory element-binding protein 2]: Endoplasmic reticulum membrane 1 SREBF2
[Processed sterol regulatory element-binding protein 2]: Nucleus 1 SREBF2


文献列表

  • Xianjing Zhang, Huihui Li, Wenqiong Wang, Tong Chen, Lijiang Xuan. Lipid-Lowering Activities of Cucurbitacins Isolated from Trichosanthes cucumeroides and Their Synthetic Derivatives. Journal of natural products. 2020 12; 83(12):3536-3544. doi: 10.1021/acs.jnatprod.0c00364. [PMID: 33269591]
  • Yushuang Liu, Guangying Chen, Xiaoyu Chen, Shi-Xin Chen, Li-She Gan, Tao Yuan. Colocynthenins A-D, Ring-A seco-Cucurbitane Triterpenoids from the Fruits of Citrullus colocynthis. Journal of natural products. 2018 09; 81(9):2115-2119. doi: 10.1021/acs.jnatprod.8b00461. [PMID: 30183289]
  • Karen Luise Lang, Izabella Thaís Silva, Lara Almida Zimmermann, Vanessa Rocha Machado, Marina Rodrigues Teixeira, María Ivana Lapuh, Mariana Alejandra Galetti, Jorge Alejandro Palermo, Gabriela Myriam Cabrera, Lílian Sibelle Campos Bernardes, Cláudia Maria Oliveira Simões, Eloir Paulo Schenkel, Miguel Soriano Balparda Caro, Fernando Javier Durán. Synthesis and cytotoxic activity evaluation of dihydrocucurbitacin B and cucurbitacin B derivatives. Bioorganic & medicinal chemistry. 2012 May; 20(9):3016-30. doi: 10.1016/j.bmc.2012.03.001. [PMID: 22472043]
  • Chuan Chen, Shigao Qiang, Liguang Lou, Weimin Zhao. Cucurbitane-type triterpenoids from the stems of Cucumis melo. Journal of natural products. 2009 May; 72(5):824-9. doi: 10.1021/np800692t. [PMID: 19348465]
  • Jian-Chao Chen, Gao-Hong Zhang, Zhong-Quan Zhang, Ming-Hua Qiu, Yong-Tang Zheng, Liu-Meng Yang, Kai-Bei Yu. Octanorcucurbitane and cucurbitane triterpenoids from the tubers of Hemsleya endecaphylla with HIV-1 inhibitory activity. Journal of natural products. 2008 Jan; 71(1):153-5. doi: 10.1021/np0704396. [PMID: 18088099]
  • M Yamada, J Takahashi. Effect of dietary DL-ethionine on postnatal growth, and activities of liver and kidney enzymes of male chickens, Gallus domesticus. Comparative biochemistry and physiology. C: Comparative pharmacology. 1977; 58(2C):177-81. doi: 10.1016/0306-4492(77)90101-0. [PMID: 23931]