Doxorubicinol (BioDeep_00000025037)
human metabolite Endogenous blood metabolite
代谢物信息卡片
(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-[(1S)-1,2-dihydroxyethyl]-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
化学式: C27H31NO11 (545.1897016)
中文名称:
谱图信息:
最多检出来源 Homo sapiens(blood) 14.93%
分子结构信息
SMILES: CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(CO)O)O)N)O
InChI: InChI=1S/C27H31NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15-17,22,29-31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,16-,17-,22+,27-/m0/s1
描述信息
Doxorubicinol belongs to the family of Anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.
同义名列表
9 个代谢物同义名
(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-[(1S)-1,2-dihydroxyethyl]-6,8,11-trihydroxy-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione; (8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-8-[(1S)-1,2-dihydroxyethyl]-6,8,11-trihydroxy-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione; Adriamycinol, 8S-(8alpha,8R*,10alpha)-isomer; Adriamycinol hydrochloride; 13-Dihydrodoxorubicin; Antibiotic 27706Rp; Doxorubicinol; Adriamycinol; DOXOL
数据库引用编号
7 个数据库交叉引用编号
- ChEBI: CHEBI:133817
- PubChem: 83970
- HMDB: HMDB0041884
- ChEMBL: CHEMBL3277946
- chemspider: 75768
- CAS: 54193-28-1
- PMhub: MS000173815
分类词条
相关代谢途径
BioCyc(0)
PlantCyc(0)
代谢反应
38 个相关的代谢反应过程信息。
Reactome(36)
- Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Biological oxidations:
H+ + Oxygen + TPNH + aflatoxin B1 ⟶ AFXBO + H2O + TPN - Phase I - Functionalization of compounds:
H+ + Oxygen + TPNH + aflatoxin B1 ⟶ AFXBO + H2O + TPN - Metabolism:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA - Biological oxidations:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN - Phase I - Functionalization of compounds:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN - Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Biological oxidations:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN - Phase I - Functionalization of compounds:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN - Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Biological oxidations:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN - Phase I - Functionalization of compounds:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN - Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Biological oxidations:
H+ + Oxygen + TPNH + progesterone ⟶ 11DCORST + H2O + TPN - Phase I - Functionalization of compounds:
H+ + Oxygen + TPNH + progesterone ⟶ 11DCORST + H2O + TPN - Metabolism:
3alpha,7alpha,12alpha-trihydroxy-5beta-cholest-24-one-CoA + CoA-SH ⟶ choloyl-CoA + propionyl CoA - Biological oxidations:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN - Phase I - Functionalization of compounds:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN - Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Biological oxidations:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN - Phase I - Functionalization of compounds:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN - Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Biological oxidations:
H+ + Oxygen + TPNH + aflatoxin B1 ⟶ AFXBO + H2O + TPN - Phase I - Functionalization of compounds:
H+ + Oxygen + TPNH + aflatoxin B1 ⟶ AFXBO + H2O + TPN - Metabolism:
2MACA-CoA + CoA ⟶ Ac-CoA + PROP-CoA - Biological oxidations:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN - Phase I - Functionalization of compounds:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN - Metabolism:
ATP + PROP-CoA + carbon dioxide ⟶ ADP + MEMA-CoA + Pi - Biological oxidations:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN - Phase I - Functionalization of compounds:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN - Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Biological oxidations:
H+ + Oxygen + TPNH + aflatoxin B1 ⟶ AFXBO + H2O + TPN - Phase I - Functionalization of compounds:
H+ + Oxygen + TPNH + aflatoxin B1 ⟶ AFXBO + H2O + TPN - Metabolism:
1-3-oxo-THA-CoA + CoA-SH ⟶ DHA-CoA + propionyl CoA - Biological oxidations:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN - Phase I - Functionalization of compounds:
11DCORT + H+ + Oxygen + TPNH ⟶ CORT + H2O + TPN
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(1)
- Doxorubicin Metabolism Pathway:
Adenosine triphosphate + Doxorubicin + Water ⟶ Adenosine diphosphate + Doxorubicin + Phosphate
1 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。
文献列表
- Lara Zorić, Nikša Drinković, Vedran Micek, Leo Frkanec, Akif Emre Türeli, Nazende Günday-Türeli, Ivana Vinković Vrček, Ruža Frkanec. High-Throughput Method for the Simultaneous Determination of Doxorubicin Metabolites in Rat Urine after Treatment with Different Drug Nanoformulations.
Molecules (Basel, Switzerland).
2022 Feb; 27(4):. doi:
10.3390/molecules27041177. [PMID: 35208967] - Yuhuan Ji, Xueyuan Zhang, Jinzhi Liu, Yu Chen, Min Meng, ChunLei Li, Laixin Wang. Direct quantitation of free, encapsulated, total doxorubicin and doxorubicinol in stabilized frozen human plasma to support a BE study of liposomal doxorubicin.
Journal of pharmaceutical and biomedical analysis.
2020 Sep; 189(?):113388. doi:
10.1016/j.jpba.2020.113388. [PMID: 32663760] - Leandro Francisco Pippa, Milena Locci de Oliveira, Adriana Rocha, Jurandyr Moreira de Andrade, Vera Lucia Lanchote. Total, renal and hepatic clearances of doxorubicin and formation clearance of doxorubicinol in patients with breast cancer: Estimation of doxorubicin hepatic extraction ratio.
Journal of pharmaceutical and biomedical analysis.
2020 Jun; 185(?):113231. doi:
10.1016/j.jpba.2020.113231. [PMID: 32163849] - Won-Gu Choi, Dong Kyun Kim, Yongho Shin, Ria Park, Yong-Yeon Cho, Joo Young Lee, Han Chang Kang, Hye Suk Lee. Liquid Chromatography-Tandem Mass Spectrometry for the Simultaneous Determination of Doxorubicin and its Metabolites Doxorubicinol, Doxorubicinone, Doxorubicinolone, and 7-Deoxydoxorubicinone in Mouse Plasma.
Molecules (Basel, Switzerland).
2020 Mar; 25(5):. doi:
10.3390/molecules25051254. [PMID: 32164308] - Lingling Shan, Guizhen Gao, Weiwei Wang, Wei Tang, Zhantong Wang, Zhen Yang, Wenpei Fan, Guizhi Zhu, Kefeng Zhai, Orit Jacobson, Yunlu Dai, Xiaoyuan Chen. Self-assembled green tea polyphenol-based coordination nanomaterials to improve chemotherapy efficacy by inhibition of carbonyl reductase 1.
Biomaterials.
2019 07; 210(?):62-69. doi:
10.1016/j.biomaterials.2019.04.032. [PMID: 31075724] - Luke A Wittenburg, Kristen Weishaar, Dominique Ramirez, Daniel L Gustafson. Doxorubicin area under the curve is an important predictor of neutropenia in dogs with naturally occurring cancers.
Veterinary and comparative oncology.
2019 Jun; 17(2):147-154. doi:
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2013 Nov; 347(2):375-87. doi:
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Journal of nutritional science and vitaminology.
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2009 Jul; 64(2):243-51. doi:
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Talanta.
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Toxicology and applied pharmacology.
2007 Nov; 225(1):90-101. doi:
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