2-Hydroxyestradiol (BioDeep_00000001748)
Main id: BioDeep_00000637477
human metabolite Endogenous
代谢物信息卡片
(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-4,5,14-triol
化学式: C18H24O3 (288.1725354)
中文名称: 2-羟基-17β-雌二醇
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC12CCC3C(C1CCC2O)CCC4=CC(=C(C=C34)O)O
InChI: InChI=1S/C18H24O3/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-15(19)16(20)9-13(10)11/h8-9,11-12,14,17,19-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1
描述信息
2-Hydroxyestradiol (2-OHE2), also known as estra-1,3,5(10)-triene-2,3,17beta-triol, is an endogenous steroid, catechol estrogen. 2-Hydroxyestradiol belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 2-hydroxyestradiol is considered to be a steroid molecule. It is a metabolite of estradiol, as well as a positional isomer of estriol. Transformation of estradiol to 2-hydroxyestradiol is a major metabolic pathway of estradiol in the liver. 2-Hydroxyestradiol is generated from estradiol via several cytochrome P450 enzymes. Specifically, CYP1A2 and CYP3A4 are the major enzymes catalyzing the 2-hydroxylation of estradiol. Conversion of estradiol into 2-hydroxyestradiol has been detected in the liver, uterus, breast, kidney, brain, and pituitary gland, as well as the placenta. 2-Hydroxyestradiol binds, with a low affinity, to estrogen receptors. 2-Hydroxyestradiol has approximately 7\\% and 11\\% of the affinity of estradiol at the estrogen receptors (ERs) ERalpha and ERbeta, respectively (PMID: 9048584). 2-Hydroxyestradiol is a catechol estrogen and in this regard bears some structural resemblance to the catecholamines dopamine, norepinephrine (noradrenaline), and epinephrine (adrenaline) (PMID: 447670). In accordance, 2-hydroxyestradiol has been found to interact with catecholamine systems. The steroid is known to compete with catecholamines for binding to catechol O-methyltransferase and tyrosine hydroxylase and to competitively inhibit these enzymes (PMID: 447670). Inactivity of COMT blocks inactivation of catechol hormones and catecholamine neurotransmitters. 2-Hydroxyestradiol is also reported to inhibit angiongensis and tumor cell growth (PMID: 9472688).
2-Hydroxyestradiol is generated from estradiol by a Cytochrome P450. 2-Hydroxyestradiol binds, with a low affinity, to estrogen receptors. It inhbits catechol-O-methyltransferase (COMT) activity. Inactivity of COMT blocks inactivation of catechol hormones and catecholamine neutransmitters. 2-Hydroxyestradiol is also reported to inhibit angiongensis and tumor cell growth (PMID: 9472688). [HMDB]
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone
C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C483 - Therapeutic Estrogen
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
同义名列表
27 个代谢物同义名
(1S,10R,11S,14S,15S)-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-triene-4,5,14-triol; Estra-1,3,5(10)-triene-2,3,17-triol (acd/name 4.0); (17beta)- Estra-1,3, 5 (10)-triene-2,3,17-triol; (17beta)-Estra-1,3,5(10)-triene-2,3,17-triol; (17b)-Estra-1,3, 5(10)-triene-2,3,17-triol; Estra-1,3,5 (10)-triene-2,3,17.beta.-triol; (17Β)-estra-1,3,5(10)-triene-2,3,17-triol; (17b)-Estra-1,3,5(10)-triene-2,3,17-triol; 2,3,17b-Trihydroxyestra-1,3,5(10)-triene; Estra-1,3,5(10)-triene-2,3,17-beta-triol; estra-1,3,5(10)-triene-2,3,17beta-triol; 1,3,5(10)-Estratriene-2,3,17Beta-triol; Estra-1,3,5(10)-triene-2,3,17b-triol; 2-Hydroxyestradiol, (17alpha)-isomer; 2-Hydroxyestradiol, 4-(14)C-labeled; 2-Hydroxyestradiol-17 alpha; 2-Hydroxy-17beta-estradiol; 2-hydroxyestradiol-17 beta; 2-Hydroxyestradiol-17beta; 17beta-2-Hydroxyestradiol; 2-Hydroxyestradiol-17β; 2-Hydroxyestradiol-17b; 2-Hydroxy-estradiol; 2-Hydroxyestradiol; 2-OH-Estradiol; 2-OH-e2; ECS
数据库引用编号
18 个数据库交叉引用编号
- ChEBI: CHEBI:28744
- KEGG: C05301
- PubChem: 247304
- PubChem: 9684
- HMDB: HMDB0000338
- Metlin: METLIN5327
- DrugBank: DB07706
- ChEMBL: CHEMBL467987
- Wikipedia: 2-Hydroxyestradiol
- foodb: FDB021962
- chemspider: 216475
- CAS: 362-05-0
- PMhub: MS000001091
- PubChem: 7685
- LipidMAPS: LMST02010027
- PDB-CCD: ECS
- NIKKAJI: J108.138A
- RefMet: 2-Hydroxyestradiol
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
2 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(2)
- Estrogen metabolism:
2-Methoxyestradiol ⟶ 2-methoxy-17beta-estradiol 3-glucuronide - Estrogen metabolism:
2-Methoxyestrone ⟶ 2-Methoxyestrone 3-glucuronide
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
5 个相关的物种来源信息
- 9606 Homo sapiens:
- 3708 Brassica napus: 10.3389/FNUT.2022.822033
- 9606 Homo sapiens:
- 3708 Brassica napus: 10.3389/FNUT.2022.822033
- 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
- Nhung Le, Melissa Cregger, Veronica Brown, Julio Loret de Mola, Pamela Bremer, Lyn Nguyen, Kathleen Groesch, Teresa Wilson, Paula Diaz-Sylvester, Andrea Braundmeier-Fleming. Association of microbial dynamics with urinary estrogens and estrogen metabolites in patients with endometriosis.
PloS one.
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Biochemical pharmacology.
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The Journal of steroid biochemistry and molecular biology.
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Toxicological sciences : an official journal of the Society of Toxicology.
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Reproductive sciences (Thousand Oaks, Calif.).
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Andrology.
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Breast cancer : basic and clinical research.
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2008 Nov; 112(1-3):32-9. doi:
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BMC endocrine disorders.
2008 Sep; 8(?):10. doi:
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2008 May; 110(1-2):157-62. doi:
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Gender medicine.
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Reproduction (Cambridge, England).
2007 Dec; 134(6):831-9. doi:
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Breast cancer research and treatment.
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Lipids.
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