Mestranol (BioDeep_00000003237)

human metabolite blood metabolite Chemicals and Drugs

代谢物信息卡片

(1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-ol

化学式: C21H26O2 (310.1932696)
中文名称: 美雌醇
谱图信息: 最多检出来源 Viridiplantae(plant) 1.23%

分子结构信息

SMILES: C#CC1(O)CCC2C3CCc4cc(OC)ccc4C3CCC21C
InChI: InChI=1S/C21H26O2/c1-4-21(22)12-10-19-18-7-5-14-13-15(23-3)6-8-16(14)17(18)9-11-20(19,21)2/h1,6,8,13,17-19,22H,5,7,9-12H2,2-3H3/t17-,18-,19+,20+,21+/m1/s1

描述信息

Mestranol is only found in individuals that have used or taken this drug. It is the 3-methyl ether of ethinyl estradiol. It must be demethylated to be biologically active. It is used as the estrogen component of many combination ORAL contraceptives. [PubChem]Mestranol is the 3-methyl ether of ethinylestradiol. Ethinylestradiol, is a synthetic derivative of estradiol. Ethinylestradiol is orally bio-active and the estrogen used in almost all modern formulations of combined oral contraceptive pills. It binds to (and activates) the estrogen receptor. Mestranol is a biologically inactive prodrug of ethinylestradiol to which it is demethylated in the liver with a conversion efficiency of 70\\%.Estrogens diffuse into their target cells and interact with a protein receptor. Target cells include the female reproductive tract, the mammary gland, the hypothalamus, and the pituitary. Estrogens increase the hepatic synthesis of sex hormone binding globulin (SHBG), thyroid-binding globulin (TBG), and other serum proteins and suppress follicle-stimulating hormone (FSH) from the anterior pituitary. The combination of an estrogen with a progestin suppresses the hypothalamic-pituitary system, decreasing the secretion of gonadotropin-releasing hormone (GnRH).
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D004967 - Estrogens
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen
D012102 - Reproductive Control Agents > D003270 - Contraceptive Agents

同义名列表

21 个代谢物同义名

(1S,10R,11S,14R,15S)-14-ethynyl-5-methoxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-ol; (+)-17alpha-Ethynyl-17beta-hydroxy-3-methoxy-1,3,5(10)-oestratriene; (+)-17alpha-Ethynyl-17beta-hydroxy-3-methoxy-1,3,5(10)-estratriene; (+)-17a-Ethynyl-17b-hydroxy-3-methoxy-1,3,5(10)-oestratriene; (+)-17Α-ethynyl-17β-hydroxy-3-methoxy-1,3,5(10)-oestratriene; (+)-17Α-ethynyl-17β-hydroxy-3-methoxy-1,3,5(10)-estratriene; (+)-17a-Ethynyl-17b-hydroxy-3-methoxy-1,3,5(10)-estratriene; 3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17beta-ol; 17-Ethynyl-3-methoxyoestra-1(10),2,4-trien-17beta-ol; 3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17b-ol; 3-Methoxy-19-norpregna-1,3,5(10)-trien-20-yn-17β-ol; 17-Ethynyl-3-methoxyoestra-1(10),2,4-trien-17β-ol; 17-Ethynyl-3-methoxyoestra-1(10),2,4-trien-17b-ol; 3-Methoxy-17alpha-ethynylestradiol; Ethinyl estradiol 3 methyl ether; Ethinyl estradiol 3-methyl ether; Ethynylestradiol 3-methyl ether; 3-Methoxy-17a-ethynylestradiol; 3-Methoxy-17α-ethynylestradiol; Mestranolum; Mestranol

数据库引用编号

18 个数据库交叉引用编号

ChEBI: CHEBI:6784
KEGG: C76306
KEGG: C07618
KEGGdrug: D00575
PubChem: 6291
HMDB: HMDB0015446
Metlin: METLIN1156
DrugBank: DB01357
ChEMBL: CHEMBL1201151
Wikipedia: Mestranol
MeSH: Mestranol
KNApSAcK: C00032009
chemspider: 6054
CAS: 72-33-3
PMhub: MS000008561
PubChem: 9820
NIKKAJI: J1.426E
RefMet: Mestranol

分类词条

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)

2 个相关的物种来源信息

4853 - Cunninghamella elegans: 10.1248/CPB.53.1011
9606 - Homo sapiens: -

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

Zihao Zhou, Hongying Wu, Zhengjun Wu, Lili Mo, Dinghong Li, Wenlong Zeng, Haiyu Luo, Jinlong Huang. Identification of sex pheromone of red swamp crayfish Procambarus clarkii and exploration of the chemosensory mechanism of their antennae. Pesticide biochemistry and physiology. 2023 Sep; 195(?):105580. doi: 10.1016/j.pestbp.2023.105580. [PMID: 37666605]
Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
Ankur Kumar Tanwar, Neha Dhiman, Amit Kumar, Vikas Jaitak. Engagement of phytoestrogens in breast cancer suppression: Structural classification and mechanistic approach. European journal of medicinal chemistry. 2021 Mar; 213(?):113037. doi: 10.1016/j.ejmech.2020.113037. [PMID: 33257172]
Tobie D Lee, Olivia W Lee, Kyle R Brimacombe, Lu Chen, Rajarshi Guha, Sabrina Lusvarghi, Bethilehem G Tebase, Carleen Klumpp-Thomas, Robert W Robey, Suresh V Ambudkar, Min Shen, Michael M Gottesman, Matthew D Hall. A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein. Molecular pharmacology. 2019 11; 96(5):629-640. doi: 10.1124/mol.119.115964. [PMID: 31515284]
Martin Perreault, René Maltais, Jenny Roy, Raphaël Dutour, Donald Poirier. Design of a Mestranol 2-N-Piperazino-Substituted Derivative Showing Potent and Selective in vitro and in vivo Activities in MCF-7 Breast Cancer Models. ChemMedChem. 2017 01; 12(2):177-182. doi: 10.1002/cmdc.201600482. [PMID: 28060448]
Ivana Matić Bujagić, Svetlana Grujić, Zorica Jauković, Mila Laušević. Sterol ratios as a tool for sewage pollution assessment of river sediments in Serbia. Environmental pollution (Barking, Essex : 1987). 2016 Jun; 213(?):76-83. doi: 10.1016/j.envpol.2015.12.036. [PMID: 26874877]
Huixiao Hong, William S Branham, Hui Wen Ng, Carrie L Moland, Stacey L Dial, Hong Fang, Roger Perkins, Daniel Sheehan, Weida Tong. Human sex hormone-binding globulin binding affinities of 125 structurally diverse chemicals and comparison with their binding to androgen receptor, estrogen receptor, and α-fetoprotein. Toxicological sciences : an official journal of the Society of Toxicology. 2015 Feb; 143(2):333-48. doi: 10.1093/toxsci/kfu231. [PMID: 25349334]
Huixiao Hong, William S Branham, Stacey L Dial, Carrie L Moland, Hong Fang, Jie Shen, Roger Perkins, Daniel Sheehan, Weida Tong. Rat α-Fetoprotein binding affinities of a large set of structurally diverse chemicals elucidated the relationships between structures and binding affinities. Chemical research in toxicology. 2012 Nov; 25(11):2553-66. doi: 10.1021/tx3003406. [PMID: 23013281]
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