Daunorubicin (BioDeep_00000398422)

Main id: BioDeep_00000002594

 

natural product Chemicals and Drugs Antibiotics


代谢物信息卡片


Daunorubicin

化学式: C27H29NO10 (527.1791)
中文名称: 柔红霉素
谱图信息: 最多检出来源 Homo sapiens(urine) 50%

分子结构信息

SMILES: c(=O)(c12)c(c5O[H])c(c(O[H])c(c35)C(C(C(C3(OC([H])(C([H])([H])4)OC([H])(C([H])(O[H])C([H])(N([H])[H])4)C([H])([H])[H])[H])([H])[H])(O[H])C(=O)C([H])([H])[H])([H])[H])c(c1c(c(c(c2OC([H])([H])[H])[H])[H])[H])=O
InChI: InChI=1S/C27H29NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3

描述信息

L - Antineoplastic and immunomodulating agents > L01 - Antineoplastic agents > L01D - Cytotoxic antibiotics and related substances > L01DB - Anthracyclines and related substances
C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor > C129824 - Antineoplastic Protein Inhibitor
D000970 - Antineoplastic Agents > D059003 - Topoisomerase Inhibitors > D059005 - Topoisomerase II Inhibitors
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C259 - Antineoplastic Antibiotic
C471 - Enzyme Inhibitor > C129825 - Antineoplastic Enzyme Inhibitor > C1748 - Topoisomerase Inhibitor
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C2842 - DNA Binding Agent
A natural product found in Actinomadura roseola.
D004791 - Enzyme Inhibitors

同义名列表

2 个代谢物同义名

Daunorubicin; Daunorubicin



数据库引用编号

37 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)

382 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 ABCB1, ACE, BRCA1, CBR3, CD34, EGFR, MAPK14, MTOR, MYC, NFKB1, NPM1, NQO1, TUBB4B
Peripheral membrane protein 1 MTOR
Endosome membrane 3 EGFR, FLT3, TF
Endoplasmic reticulum membrane 2 EGFR, MTOR
Nucleus 10 BRCA1, EGFR, MAPK14, MTOR, MYC, NFKB1, NPM1, NQO1, PARP1, TUBB4B
cytosol 8 CBR3, MAPK14, MTOR, NFKB1, NPM1, NQO1, PARP1, TUBB4B
dendrite 2 MTOR, NQO1
nuclear body 2 BRCA1, PARP1
phagocytic vesicle 1 MTOR
centrosome 1 NPM1
nucleoplasm 9 BRCA1, CBR3, CD33, MAPK14, MTOR, MYC, NFKB1, NPM1, PARP1
Cell membrane 4 ABCB1, ACE, CD8A, EGFR
Cytoplasmic side 1 MTOR
ruffle membrane 1 EGFR
Early endosome membrane 1 EGFR
Multi-pass membrane protein 1 ABCB1
Golgi apparatus membrane 1 MTOR
Synapse 1 NQO1
cell junction 1 EGFR
cell surface 4 ABCB1, CD33, EGFR, TF
glutamatergic synapse 2 EGFR, MAPK14
Golgi apparatus 1 CD33
Golgi membrane 2 EGFR, MTOR
lysosomal membrane 1 MTOR
neuronal cell body 1 NQO1
Cytoplasm, cytosol 2 NQO1, PARP1
Lysosome 3 ACE, CD34, MTOR
endosome 2 ACE, EGFR
plasma membrane 10 ABCB1, ACE, BRCA1, CD33, CD34, CD8A, CSF2, EGFR, FLT3, TF
Membrane 12 ABCB1, ACE, BRCA1, CD33, CD34, EGFR, FLT3, MTOR, MYC, NPM1, NQO1, PARP1
apical plasma membrane 4 ABCB1, CD34, EGFR, TF
basolateral plasma membrane 1 EGFR
extracellular exosome 4 ABCB1, ACE, TF, TUBB4B
Lysosome membrane 1 MTOR
endoplasmic reticulum 1 FLT3
extracellular space 5 ACE, CBR3, CSF2, EGFR, TF
perinuclear region of cytoplasm 3 CD34, EGFR, TF
mitochondrion 3 MAPK14, NFKB1, PARP1
protein-containing complex 5 BRCA1, EGFR, MYC, NPM1, PARP1
intracellular membrane-bounded organelle 1 CSF2
Microsome membrane 1 MTOR
TORC1 complex 1 MTOR
TORC2 complex 1 MTOR
Single-pass type I membrane protein 5 ACE, CD34, CD8A, EGFR, FLT3
Secreted 3 ACE, CSF2, TF
extracellular region 8 ACE, CD34, CD8A, CSF2, MAPK14, NFKB1, TF, TUBB4B
Mitochondrion outer membrane 1 MTOR
Single-pass membrane protein 1 CD33
mitochondrial outer membrane 1 MTOR
basal part of cell 1 TF
[Isoform 2]: Secreted 1 CD8A
transcription regulator complex 2 NFKB1, PARP1
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 NPM1
nuclear membrane 1 EGFR
external side of plasma membrane 4 ACE, CD33, CD34, CD8A
Extracellular vesicle 1 TUBB4B
cytoplasmic vesicle 1 TF
microtubule cytoskeleton 1 TUBB4B
nucleolus 3 MYC, NPM1, PARP1
Early endosome 1 TF
clathrin-coated pit 1 TF
recycling endosome 1 TF
vesicle 1 TF
Apical cell membrane 1 ABCB1
Membrane raft 1 EGFR
Cytoplasm, cytoskeleton 1 TUBB4B
focal adhesion 2 EGFR, NPM1
microtubule 1 TUBB4B
Peroxisome 1 CD33
intracellular vesicle 1 EGFR
Nucleus, PML body 1 MTOR
PML body 1 MTOR
nuclear speck 1 MAPK14
Late endosome 1 TF
receptor complex 3 CD8A, EGFR, FLT3
chromatin 3 MYC, NFKB1, PARP1
mitotic spindle 1 TUBB4B
Chromosome 2 BRCA1, PARP1
cytoskeleton 1 TUBB4B
[Isoform 5]: Cytoplasm 1 BRCA1
brush border membrane 1 ACE
Nucleus, nucleolus 3 MYC, NPM1, PARP1
spindle pole 1 MAPK14
nuclear replication fork 1 PARP1
chromosome, telomeric region 1 PARP1
blood microparticle 1 TF
sperm midpiece 1 ACE
site of double-strand break 1 PARP1
intercellular bridge 2 CD34, TUBB4B
Cytoplasm, cytoskeleton, flagellum axoneme 1 TUBB4B
sperm flagellum 1 TUBB4B
nuclear envelope 3 MTOR, MYC, PARP1
Endomembrane system 1 MTOR
axonemal microtubule 1 TUBB4B
lateral element 1 BRCA1
Nucleus, nucleoplasm 2 MYC, NPM1
specific granule membrane 1 CD33
tertiary granule membrane 1 CD33
ubiquitin ligase complex 1 BRCA1
basal plasma membrane 4 ACE, CD34, EGFR, TF
synaptic membrane 1 EGFR
plasma membrane raft 1 CD8A
ficolin-1-rich granule lumen 1 MAPK14
secretory granule lumen 3 MAPK14, NFKB1, TF
HFE-transferrin receptor complex 1 TF
endoplasmic reticulum lumen 2 FLT3, TF
male germ cell nucleus 1 BRCA1
specific granule lumen 1 NFKB1
XY body 1 BRCA1
endocytic vesicle 1 TF
RNA polymerase II transcription repressor complex 1 MYC
azurophil granule lumen 1 TUBB4B
clathrin-coated endocytic vesicle membrane 2 EGFR, TF
spindle pole centrosome 1 NPM1
ribonucleoprotein complex 2 BRCA1, NPM1
protein-DNA complex 2 NPM1, PARP1
external side of apical plasma membrane 1 ABCB1
[Isoform 1]: Cell membrane 1 CD8A
intracellular non-membrane-bounded organelle 1 BRCA1
Rough endoplasmic reticulum 1 MYC
DNA repair complex 1 BRCA1
Cytoplasmic vesicle, phagosome 1 MTOR
granulocyte macrophage colony-stimulating factor receptor complex 1 CSF2
BRCA1-C complex 1 BRCA1
site of DNA damage 1 PARP1
granular component 1 NPM1
vesicle coat 1 TF
multivesicular body, internal vesicle lumen 1 EGFR
Shc-EGFR complex 1 EGFR
Myc-Max complex 1 MYC
T cell receptor complex 1 CD8A
[Poly [ADP-ribose] polymerase 1, processed N-terminus]: Chromosome 1 PARP1
[Poly [ADP-ribose] polymerase 1, processed C-terminus]: Cytoplasm 1 PARP1
[Angiotensin-converting enzyme, soluble form]: Secreted 1 ACE
[Isoform Testis-specific]: Cell membrane 1 ACE
[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
[Isoform CD33M]: Cell membrane 1 CD33
[Isoform CD33m]: Peroxisome 1 CD33
glomerular endothelium fenestra 1 CD34
BRCA1-A complex 1 BRCA1
BRCA1-B complex 1 BRCA1
BRCA1-BARD1 complex 1 BRCA1
gamma-tubulin ring complex 1 BRCA1
nuclear ubiquitin ligase complex 1 BRCA1
dense body 1 TF
nucleoplasmic reticulum 1 MYC


文献列表

  • Ioannis Isaioglou, Gloria Lopez-Madrigal, Jasmeen S Merzaban. A fast, easy, cost-free method to remove excess dye or drug from small extracellular vesicle solution. PloS one. 2024; 19(5):e0301761. doi: 10.1371/journal.pone.0301761. [PMID: 38718025]
  • Qi Liu, Lijun Luo, Xiaofeng Gao, Di Zhang, Xinqian Feng, Peng Yang, Hui Li, Shengjun Mao. Co-Delivery of Daunorubicin and Homoharringtonine in Folic Acid Modified-Liposomes for Enhancing Therapeutic Effect on Acute Myeloid Leukemia. Journal of pharmaceutical sciences. 2023 01; 112(1):123-131. doi: 10.1016/j.xphs.2022.04.014. [PMID: 35469834]
  • Yuanyuan Zhu, Wei Zhang, Jing Chen. Binary Nanodrug-Delivery System Designed for Leukemia Therapy: Aptamer- and Transferrin-Codecorated Daunorubicin- and Luteolin-Coloaded Nanoparticles. Drug design, development and therapy. 2023; 17(?):1-13. doi: 10.2147/dddt.s387246. [PMID: 36636745]
  • Angelina Subeska, Jan Althaus, Theresa Hake, Walburga Hanekamp, Dominik Bettenworth, Dennis Mulac, Klaus Langer, Matthias Lehr. Synthesis and pharmacokinetic properties of novel cPLA2α inhibitors with 1-(carboxyalkylpyrrolyl)-3-aryloxypropan-2-one structure. Bioorganic & medicinal chemistry. 2023 01; 77(?):117110. doi: 10.1016/j.bmc.2022.117110. [PMID: 36495814]
  • Hamad Alrbyawi, Sai H S Boddu, Ishwor Poudel, Manjusha Annaji, Nur Mita, Robert D Arnold, Amit K Tiwari, R Jayachandra Babu. Cardiolipin for Enhanced Cellular Uptake and Cytotoxicity of Thermosensitive Liposome-Encapsulated Daunorubicin toward Breast Cancer Cell Lines. International journal of molecular sciences. 2022 Oct; 23(19):. doi: 10.3390/ijms231911763. [PMID: 36233061]
  • Emmanuel Gyan, Arnaud Pigneux, Mathilde Hunault, Pierre Peterlin, Martin Carré, Jacques-Olivier Bay, Caroline Bonmati, Maria-Pilar Gallego-Hernanz, Bruno Lioure, Philippe Bertrand, Nicolas Vallet, David Ternant, François Darrouzain, Frédéric Picou, Marie-Christine Béné, Christian Récher, Olivier Hérault. Adjunction of a fish oil emulsion to cytarabine and daunorubicin induction chemotherapy in high-risk AML. Scientific reports. 2022 06; 12(1):9748. doi: 10.1038/s41598-022-13626-y. [PMID: 35697729]
  • Sha Li, Shi Zeng, Bo-Ping Wei, Qiang Wu, Chang Liu, Pei-Ying Song. Determination of free and encapsulated cytarabine and daunorubicin in rat plasma after intravenous administration of liposomal formulation using ultra-high performance liquid chromatography tandem mass spectrometry. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2022 Jun; 1200(?):123275. doi: 10.1016/j.jchromb.2022.123275. [PMID: 35551041]
  • Riya Sinha, Arunavo Chatterjee, Pradipta Purkayastha. Graphene Quantum Dot Assisted Translocation of Daunomycin through an Ordered Lipid Membrane: A Study by Fluorescence Lifetime Imaging Microscopy and Resonance Energy Transfer. The journal of physical chemistry. B. 2022 02; 126(6):1232-1241. doi: 10.1021/acs.jpcb.1c09376. [PMID: 35129981]
  • Zuzana Pokorná, Petra Kollárová-Brázdová, Olga Lenčová-Popelová, Eduard Jirkovský, Jan Kubeš, Yvona Mazurová, Michaela Adamcová, Magdalena Holečková, Vladimír Palička, Tomáš Šimůnek, Martin Štěrba. Primary prevention of chronic anthracycline cardiotoxicity with ACE inhibitor is temporarily effective in rabbits, but benefits wane in post-treatment follow-up. Clinical science (London, England : 1979). 2022 01; 136(1):139-161. doi: 10.1042/cs20210836. [PMID: 34878093]
  • Claire Amaris Hobson, Lucile Vigué, Mélanie Magnan, Benoit Chassaing, Sabrine Naimi, Benoit Gachet, Pauline Claraz, Thomas Storme, Stephane Bonacorsi, Olivier Tenaillon, André Birgy. A Microbiota-Dependent Response to Anticancer Treatment in an In Vitro Human Microbiota Model: A Pilot Study With Hydroxycarbamide and Daunorubicin. Frontiers in cellular and infection microbiology. 2022; 12(?):886447. doi: 10.3389/fcimb.2022.886447. [PMID: 35719352]
  • Mélanie Donnette, Mourad Hamimed, Joseph Ciccolini, Yael Berda-Haddad, Elise Kaspi, Geoffroy Venton, Bruno Lacarelle, Regis Costello, L''Houcine Ouafik, Laure Farnault, Raphaelle Fanciullino. Pharmacokinetics and pharmacogenetics of liposomal cytarabine in AML patients treated with CPX-351. Journal of controlled release : official journal of the Controlled Release Society. 2021 10; 338(?):244-252. doi: 10.1016/j.jconrel.2021.08.023. [PMID: 34416320]
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  • Jiaoyang Zhang, Lingli Zhou, Yu Zhang, Haibing He, Tian Yin, Jingxin Gou, Yanjiao Wang, Xing Tang. Contrastive Studies of Cytarabine/Daunorubicin Dual-Loaded Liposomes Prepared by pH Gradient and Cu2+ Gradient Method. AAPS PharmSciTech. 2020 Nov; 21(8):325. doi: 10.1208/s12249-020-01867-x. [PMID: 33206247]
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  • Huan Zhou, Li-Xiang Fu, Li Li, Yan-Yan Chen, Hong-Qing Zhu, Jin-Ling Zhou, Mei-Xian Lv, Ri-Zhi Gan, Xuan-Xuan Zhang, Gang Liang. The epigallocatechin gallate derivative Y6 reduces the cardiotoxicity and enhances the efficacy of daunorubicin against human hepatocellular carcinoma by inhibiting carbonyl reductase 1 expression. Journal of ethnopharmacology. 2020 Oct; 261(?):113118. doi: 10.1016/j.jep.2020.113118. [PMID: 32621953]
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  • Fereidoon Rahmani, Mohammad-Reza Milani Hosseini, Ali Es-Haghi, Afsaneh Mollahosseini. A 96-Monolithic inorganic hollow fiber array as a new geometry for high throughput solid-phase microextraction of doxorubicin in water and human urine samples coupled with liquid chromatography-tandem mass spectrometry. Journal of chromatography. A. 2020 Sep; 1627(?):461413. doi: 10.1016/j.chroma.2020.461413. [PMID: 32823111]
  • Qiu-Jin Yang, Jie Zheng, Fu-Tao Dang, Yue-Meng Wan, Jing Yang. Acute pancreatitis induced by combination chemotherapy used for the treatment of acute myeloid leukemia: A case report. Medicine. 2020 Aug; 99(35):e21848. doi: 10.1097/md.0000000000021848. [PMID: 32871908]
  • Wencheng Xu, Xiaoqin Wang, Shuhe Chen, Hongguang Wu, Sachiko Tanaka, Kenji Onda, Kentaro Sugiyama, Haruki Yamada, Toshihiko Hirano. Tetrandrine enhances glucocorticoid receptor translocation possibly via inhibition of P-glycoprotein in daunorubicin-resistant human T lymphoblastoid leukemia cells. European journal of pharmacology. 2020 Aug; 881(?):173232. doi: 10.1016/j.ejphar.2020.173232. [PMID: 32525004]
  • Qingwei Nong, Cong Zhang, Qinghao Liu, Rui Xie, Min Dong. Effect of daunorubicin on acute promyelocytic leukemia cells using nuclear magnetic resonance spectroscopy-based metabolomics. Environmental toxicology and pharmacology. 2020 Aug; 78(?):103382. doi: 10.1016/j.etap.2020.103382. [PMID: 32344291]
  • Nadine Farah, Richard Burt, Amr R Ibrahim, Robert Baker, Panagiotis D Kottaridis. Concerns about how to use established minimal residual disease monitoring in the treatment of NPM1-mutant acute myeloid leukaemia (AML) following reduced intensity chemotherapy protocols for AML given as a result of the COVID-19 pandemic. British journal of haematology. 2020 08; 190(4):e208-e210. doi: 10.1111/bjh.16985. [PMID: 32609881]
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  • Guillermo Montalban-Bravo, Rashmi Kanagal-Shamanna, Caleb A Class, Koji Sasaki, Farhad Ravandi, Jorge E Cortes, Naval Daver, Koichi Takahashi, Nicholas J Short, Courtney D DiNardo, Elias Jabbour, Gautam Borthakur, Kiran Naqvi, Ghayas C Issa, Marina Konopleva, Joseph D Khoury, Mark Routbort, Sherry Pierce, Kim-Anh Do, Carlos Bueso-Ramos, Keyur Patel, Hagop Kantarjian, Guillermo Garcia-Manero, Tapan M Kadia. Outcomes of acute myeloid leukemia with myelodysplasia related changes depend on diagnostic criteria and therapy. American journal of hematology. 2020 06; 95(6):612-622. doi: 10.1002/ajh.25769. [PMID: 32112433]
  • Mirza Muhammad Faran Ashraf Baig, Wing-Fu Lai, Reyaj Mikrani, Mehreen Jabeen, Muhammad Naveed, Muhammad Abbas, Muhammad Asim Farooq, Anam Ahsan, Said Abasse Kassim, Ghulam Jilany Khan, Muhammad Tayyab Ansari. Synthetic NRG-1 functionalized DNA nanospindels towards HER2/neu targets for in vitro anti-cancer activity assessment against breast cancer MCF-7 cells. Journal of pharmaceutical and biomedical analysis. 2020 Apr; 182(?):113133. doi: 10.1016/j.jpba.2020.113133. [PMID: 32004770]
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  • Min Fu, Wei Tang, Jing-Jing Liu, Xiao-Qing Gong, Liang Kong, Xue-Min Yao, Ming Jing, Fu-Yi Cai, Xue-Tao Li, Rui-Jun Ju. Combination of targeted daunorubicin liposomes and targeted emodin liposomes for treatment of invasive breast cancer. Journal of drug targeting. 2020 03; 28(3):245-258. doi: 10.1080/1061186x.2019.1656725. [PMID: 31462111]
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