Bruceantin (BioDeep_00000000572)

   

PANOMIX_OTCML-2023 Chemicals and Drugs natural product


代谢物信息卡片


methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-3-[(E)-3,4-dimethylpent-2-enoyl]oxy-10,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate

化学式: C28H36O11 (548.2258)
中文名称: 鸦胆丁, 鸦胆亭, 鸦胆停
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 93.42%

分子结构信息

SMILES: CC(C)/C(=C/C(=O)O[C@@H]1[C@@H]2[C@]34CO[C@@]2([C@H]([C@@H]([C@@H]4[C@@]2(C)CC(=O)C(=C(C)[C@@H]2C[C@H]3OC1=O)O)O)O)C(=O)OC)/C
InChI: InChI=1S/C28H36O11/c1-11(2)12(3)7-17(30)39-20-22-27-10-37-28(22,25(35)36-6)23(33)19(32)21(27)26(5)9-15(29)18(31)13(4)14(26)8-16(27)38-24(20)34/h7,11,14,16,19-23,31-33H,8-10H2,1-6H3/b12-7+/t14-,16+,19+,20+,21+,22+,23-,26-,27+,28-/m0/s1

描述信息

Bruceantin is a triterpenoid.
Bruceantin is a natural product found in Brucea javanica and Brucea antidysenterica with data available.
Bruceantin is a triterpene quassinoid antineoplastic antibiotic isolated from the plant Brucea antidysenterica. Bruceantin inhibits the peptidyl transferase elongation reaction, resulting in decreased protein and DNA synthesis. Bruceantin also has antiamoebic and antimalarial activity. (NCI04)
C274 - Antineoplastic Agent > C1931 - Antineoplastic Plant Product > C1974 - Quassinoid Agent
C784 - Protein Synthesis Inhibitor
C1907 - Drug, Natural Product
Bruceantin (NSC165563) can be extracted from B. javanica and has inhibitory effects on B16 melanoma, colon cancer 38, L1210 and leukemia P388.
Bruceantin (NSC165563) can be extracted from B. javanica and has inhibitory effects on B16 melanoma, colon cancer 38, L1210 and leukemia P388.

同义名列表

21 个代谢物同义名

methyl (1R,2S,3R,6R,8R,13S,14R,15R,16S,17S)-3-[(E)-3,4-dimethylpent-2-enoyl]oxy-10,15,16-trihydroxy-9,13-dimethyl-4,11-dioxo-5,18-dioxapentacyclo[12.5.0.01,6.02,17.08,13]nonadec-9-ene-17-carboxylate; PICRAS-3-EN-21-OIC ACID, 15-(((2E)-3,4-DIMETHYL-1-OXO-2-PENTEN-1-YL)OXY)-13,20-EPOXY-3,11,12-TRIHYDROXY-2,16-DIOXO-, METHYL ESTER, (11.BETA.,12.ALPHA.,15.BETA.)-; Picras-3-en-21-oic acid, 15-((3,4-dimethyl-1-oxo-2-pentenyl)oxy)-13,20-epoxy-3,11,12-trihydroxy-2,16-dioxo-, methyl ester, (11beta,12alpha,15beta(E))- (9CI); Picras-3-en-21-oic acid, 15-((3,4-dimethyl-1-oxo-2-pentenyl)oxy)-13,20-epoxy-3,11,12-trihydroxy-2,16-dioxo-, methyl ester, (11beta,12alpha,15beta(E))-; Picras-3-en-21-oic acid,4-dimethyl-1-oxo-2-pentenyl)oxy]-13,20-epoxy-3,11,12-trihydroxy-2,16-dioxo-, methyl ester, [11.beta.,12.alpha.,15.beta.(E)]-; Picras-3-en-21-oic acid,4-dimethyl-1-oxo-2-pentenyl)oxy]-13,20-epoxy-3,11,12-trihydroxy-2,16-dioxo-, methyl ester, (11.beta.,12.alpha.,15.beta.(E))-; Picras-3-en-21-oic acid,4-dimethyl-1-oxo-2-pentenyl)oxy]-13,20-epoxy-3,11,12-trihydroxy-2,16-dioxo-, methyl ester [11.beta.,12.alpha.,15.beta.(E]-; 2H-3,11c-(Epoxymethano)phenanthro[10,1-bc]pyran, picras-3-en-21-oic acid deriv; 2H-3,1-bc]pyran, picras-3-en-21-oic acid deriv.; IRQXZTBHNKVIRL-GOTQHHPNSA-N; UNII-S3NW88DI4T; BRUCEANTIN [MI]; Bruceantine; Bruceantin; S3NW88DI4T; Neuro_000096; (-)-Bruceantin; NCI165563; NSC165563; Bruceantin; Bruceantin



数据库引用编号

20 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)

19 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 13 ANPEP, AR, BCL2, CCND1, DHFR, HIF1A, MCL1, MTOR, MYC, NFKB1, NQO1, PTEN, PTGS1
Peripheral membrane protein 4 GORASP1, MTOR, PTGS1, PTPMT1
Endosome membrane 1 FLT3
Endoplasmic reticulum membrane 3 BCL2, MTOR, PTGS1
Nucleus 11 AR, BCL2, CCND1, HIF1A, MCL1, MTOR, MYC, NFKB1, NQO1, PTEN, PTPMT1
cytosol 11 AR, BCL2, CCND1, DHFR, HIF1A, IDH2, MCL1, MTOR, NFKB1, NQO1, PTEN
dendrite 2 MTOR, NQO1
nuclear body 1 HIF1A
phagocytic vesicle 1 MTOR
trans-Golgi network 1 FUT4
centrosome 1 CCND1
nucleoplasm 9 AR, ATP2B1, CCND1, HIF1A, MCL1, MTOR, MYC, NFKB1, PTEN
RNA polymerase II transcription regulator complex 1 HIF1A
Cell membrane 2 ANPEP, ATP2B1
Cytoplasmic side 2 GORASP1, MTOR
Multi-pass membrane protein 1 ATP2B1
Golgi apparatus membrane 2 GORASP1, MTOR
Synapse 2 ATP2B1, NQO1
cell surface 1 FUT4
glutamatergic synapse 1 ATP2B1
Golgi apparatus 3 FUT4, GORASP1, PTGS1
Golgi membrane 3 FUT4, GORASP1, MTOR
lysosomal membrane 2 ANPEP, MTOR
mitochondrial inner membrane 1 PTPMT1
neuronal cell body 1 NQO1
presynaptic membrane 1 ATP2B1
Cytoplasm, cytosol 1 NQO1
Lysosome 1 MTOR
plasma membrane 5 ANPEP, AR, ATP2B1, FLT3, PTEN
synaptic vesicle membrane 1 ATP2B1
Membrane 9 AR, ATP2B1, BCL2, FLT3, FUT4, MCL1, MTOR, MYC, NQO1
apical plasma membrane 1 PTEN
basolateral plasma membrane 1 ATP2B1
extracellular exosome 4 ANPEP, ATP2B1, IDH2, PTGS1
Lysosome membrane 1 MTOR
endoplasmic reticulum 2 BCL2, FLT3
extracellular space 2 ANPEP, CTRL
bicellular tight junction 1 CCND1
mitochondrion 6 BCL2, DHFR, IDH2, MCL1, NFKB1, PTPMT1
protein-containing complex 4 AR, BCL2, HIF1A, MYC
intracellular membrane-bounded organelle 2 ATP2B1, PTGS1
Microsome membrane 2 MTOR, PTGS1
postsynaptic density 1 PTEN
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 1 FLT3
extracellular region 2 NFKB1, PTEN
cytoplasmic side of plasma membrane 1 PTEN
Mitochondrion outer membrane 2 BCL2, MTOR
Single-pass membrane protein 2 BCL2, MCL1
mitochondrial outer membrane 3 BCL2, MCL1, MTOR
mitochondrial matrix 1 IDH2
transcription regulator complex 1 NFKB1
motile cilium 1 HIF1A
photoreceptor outer segment 1 PTGS1
Cytoplasmic vesicle, secretory vesicle, synaptic vesicle membrane 1 ATP2B1
Nucleus membrane 2 BCL2, CCND1
Bcl-2 family protein complex 2 BCL2, MCL1
nuclear membrane 2 BCL2, CCND1
external side of plasma membrane 1 ANPEP
dendritic spine 1 PTEN
nucleolus 1 MYC
axon cytoplasm 1 HIF1A
Single-pass type II membrane protein 1 ANPEP
Mitochondrion inner membrane 1 PTPMT1
Matrix side 1 PTPMT1
pore complex 1 BCL2
cis-Golgi network 1 GORASP1
Peroxisome 1 IDH2
Cell projection, dendritic spine 1 PTEN
Nucleus, PML body 2 MTOR, PTEN
PML body 2 MTOR, PTEN
lateral plasma membrane 1 ATP2B1
nuclear speck 2 AR, HIF1A
receptor complex 1 FLT3
Cell projection, neuron projection 1 PTEN
neuron projection 2 PTEN, PTGS1
chromatin 4 AR, HIF1A, MYC, NFKB1
cell projection 2 ATP2B1, PTEN
cell periphery 1 FUT4
Nucleus, nucleolus 1 MYC
Basolateral cell membrane 1 ATP2B1
nuclear envelope 2 MTOR, MYC
Endomembrane system 2 MTOR, PTGS1
myosin complex 1 MCL1
Nucleus, nucleoplasm 2 MCL1, MYC
Golgi cisterna membrane 1 FUT4
Nucleus speckle 1 HIF1A
euchromatin 1 HIF1A
Presynaptic cell membrane 1 ATP2B1
myelin sheath 1 BCL2
secretory granule lumen 1 NFKB1
secretory granule membrane 1 ANPEP
endoplasmic reticulum lumen 1 FLT3
transcription repressor complex 1 CCND1
specific granule lumen 1 NFKB1
RNA polymerase II transcription repressor complex 1 MYC
Schmidt-Lanterman incisure 1 PTEN
Endoplasmic reticulum-Golgi intermediate compartment membrane 1 GORASP1
immunological synapse 1 ATP2B1
Golgi apparatus, cis-Golgi network membrane 1 GORASP1
endoplasmic reticulum-Golgi intermediate compartment 1 ANPEP
Rough endoplasmic reticulum 1 MYC
Cytoplasmic vesicle, phagosome 1 MTOR
cyclin-dependent protein kinase holoenzyme complex 1 CCND1
Myc-Max complex 1 MYC
myelin sheath adaxonal region 1 PTEN
BAD-BCL-2 complex 1 BCL2
photoreceptor ribbon synapse 1 ATP2B1
cyclin D1-CDK4 complex 1 CCND1
[Isoform alpha]: Secreted 1 PTEN
[Nuclear factor NF-kappa-B p105 subunit]: Cytoplasm 1 NFKB1
[Nuclear factor NF-kappa-B p50 subunit]: Nucleus 1 NFKB1
I-kappaB/NF-kappaB complex 1 NFKB1
NF-kappaB p50/p65 complex 1 NFKB1
cyclin D1-CDK6 complex 1 CCND1
nucleoplasmic reticulum 1 MYC


文献列表

  • Yulin Ren, A Douglas Kinghorn. Development of Potential Antitumor Agents from the Scaffolds of Plant-Derived Terpenoid Lactones. Journal of medicinal chemistry. 2020 12; 63(24):15410-15448. doi: 10.1021/acs.jmedchem.0c01449. [PMID: 33289552]
  • Yoshihide Usami, Kyoko Nakagawa-Goto, Jing-Yu Lang, Yoon Kim, Chin-Yu Lai, Masuo Goto, Nobuko Sakurai, Masahiko Taniguchi, Toshiyuki Akiyama, Susan L Morris-Natschke, Kenneth F Bastow, Gordon Cragg, David J Newman, Mihoyo Fujitake, Koichi Takeya, Mien-Chie Hung, Eva Y-H P Lee, Kuo-Hsiung Lee. Antitumor Agents. 282. 2'-(R)-O-acetylglaucarubinone, a quassinoid from Odyendyea gabonensis as a potential anti-breast and anti-ovarian cancer agent. Journal of natural products. 2010 Sep; 73(9):1553-8. doi: 10.1021/np100406d. [PMID: 20738103]
  • Jeong-Ah Kim, Edward K Lau, Li Pan, Esperanza J Carcache De Blanco. NF-kappaB inhibitors from Brucea javanica exhibiting intracellular effects on reactive oxygen species. Anticancer research. 2010 Sep; 30(9):3295-300. doi: . [PMID: 20944100]
  • John A Beutler, Moon-Il Kang, Francis Robert, Jason A Clement, Jerry Pelletier, Nancy H Colburn, Tawnya C McKee, Ekaterina Goncharova, James B McMahon, Curtis J Henrich. Quassinoid inhibition of AP-1 function does not correlate with cytotoxicity or protein synthesis inhibition. Journal of natural products. 2009 Mar; 72(3):503-6. doi: 10.1021/np800732n. [PMID: 19199792]
  • G T Tan, J M Pezzuto, A D Kinghorn, S H Hughes. Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. Journal of natural products. 1991 Jan; 54(1):143-54. doi: 10.1021/np50073a012. [PMID: 1710653]
  • C W Wright, M J O'Neill, J D Phillipson, D C Warhurst. Use of microdilution to assess in vitro antiamoebic activities of Brucea javanica fruits, Simarouba amara stem, and a number of quassinoids. Antimicrobial agents and chemotherapy. 1988 Nov; 32(11):1725-9. doi: 10.1128/aac.32.11.1725. [PMID: 2908094]
  • G Cragg, M Suffness. Metabolism of plant-derived anticancer agents. Pharmacology & therapeutics. 1988; 37(3):425-61. doi: 10.1016/0163-7258(88)90006-x. [PMID: 3290912]
  • M J O'Neill, D H Bray, P Boardman, K L Chan, J D Phillipson, D C Warhurst, W Peters. Plants as sources of antimalarial drugs, Part 4: Activity of Brucea javanica fruits against chloroquine-resistant Plasmodium falciparum in vitro and against Plasmodium berghei in vivo. Journal of natural products. 1987 Jan; 50(1):41-8. doi: 10.1021/np50049a007. [PMID: 3298551]
  • F D Gillin, D S Reiner, M Suffness. Bruceantin, a potent amoebicide from a plant, Brucea antidysenterica. Antimicrobial agents and chemotherapy. 1982 Aug; 22(2):342-5. doi: 10.1128/aac.22.2.342. [PMID: 6100431]
  • R E Perdue. KB cell culture I. Role in discovery of antitumor agents from higher plants. Journal of natural products. 1982 Jul; 45(4):418-26. doi: 10.1021/np50022a010. [PMID: 7130986]
  • K L Fong, D H Ho, R S Benjamin, N S Brown, A Bedikian, B S Yap, C L Wiseman, W Kramer, G P Bodey. Clinical pharmacology of bruceantin by radioimmunoassay. Cancer chemotherapy and pharmacology. 1982; 9(3):169-72. doi: 10.1007/bf00257747. [PMID: 7160053]
  • W J Suling, C W Woolley, W M Shannon. Disposition and metabolism of bruceantin in the mouse. Cancer chemotherapy and pharmacology. 1979; 3(3):171-6. doi: 10.1007/bf00262418. [PMID: 527207]