16a-Hydroxyestrone (BioDeep_00000001278)
Main id: BioDeep_00000637483
human metabolite Endogenous blood metabolite Volatile Flavor Compounds
代谢物信息卡片
(1S,10R,11S,13R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one
化学式: C18H22O3 (286.15688620000003)
中文名称: 16α-羟基雌酮
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CC12CCC3C(C1CC(C2=O)O)CCC4=C3C=CC(=C4)O
InChI: InChI=1S/C18H22O3/c1-18-7-6-13-12-5-3-11(19)8-10(12)2-4-14(13)15(18)9-16(20)17(18)21/h3,5,8,13-16,19-20H,2,4,6-7,9H2,1H3/t13-,14-,15+,16-,18+/m1/s1
描述信息
16a-Hydroxyestrone or 16alpha-hydroxyestrone (16α-OH-E1 or 16a OHE1), or hydroxyestrone, is an endogenous steroidal estrogen and a major metabolite of estrone and estradiol. 16a-hydroxyestrone belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 16a-hydroxyestrone is considered to be a steroid molecule. 16a-hydroxyestrone is found in all vertebrates. Vertebrates, especially mammals, metabolizes estrogen into two major pathways and one minor. The two major pathways lead to 2-hydroxyestrone and 16a-hydroxyestrone (2-OHE1 and 16a OHE1 respectively). The minor pathway leads to 4-hydroxyestrone (4-OHE1). 2a-hydroxyestrone is considered to be the good metabolite (PMID: 8943806) as 2-hydroxyestrone does not stimulate cell growth and it blocks the action of stronger estrogens that may be carcinogenic. 16a-Hydroxyestrone, on the other hand, has a significantly stronger estrogenic activity, and studies show that it may increase the risk of breast cancer. The binding of 16a-hydroxyestrone to the estrogen receptor is reported to be covalent and irreversible (PMID: 3186693). A low urinary ratio of 2-hydroxyestrone to 16-alpha-hydroxyestrone is a strong predictor of breast cancer risk among women (PMID: 19502596).
Estrone (also oestrone) is an estrogenic hormone secreted by the ovary. Its molecular formula is C18H22O2. estrone has a melting point of 254.5 degrees Celsius. estrone is one of the three estrogens, which also include estriol and estradiol. estrone is the least prevalent of the three hormones, estradiol being prevalent almost always in a female body, estriol being prevalent primarily during pregnancy. estrone sulfate is relevant to health and disease due to its conversion to estrone sulfate, a long-lived derivative of estrone. estrone sulfate acts as a pool of estrone which can be converted as needed to the more active estradiol. [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
24 个代谢物同义名
(1S,10R,11S,13R,15S)-5,13-dihydroxy-15-methyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-2(7),3,5-trien-14-one; 3,16alpha-dihydroxy-estra-1,3,5(10)-trien-17-one; 3,16alpha-Dihydroxyestra-1,3,5(10)-trien-17-one; 3,16alpha-dihydroxy-1,3,5(10)-estratrien-17-one; 3,16a-Dihydroxy-estra-1,3,5(10)-trien-17-one; Estra-1,3,5(10)-triene-3,16alpha-diol-17-one; 3,16Α-dihydroxy-1,3,5(10)-estratrien-17-one; 3,16Α-dihydroxyestra-1,3,5(10)-trien-17-one; 3,16a-Dihydroxy-1,3,5(10)-estratrien-17-one; 3,16a-Dihydroxyestra-1,3,5(10)-trien-17-one; Estra-1,3,5(10)-triene-3,16a-diol-17-one; Estra-1,3,5(10)-triene-3,16α-diol-17-one; 16α-Hydroxyestrone; 16 alpha-Hydroxyestrone; 16-alpha-Hydroxyestrone; 16alpha-hydroxyestrone; 16 beta-Hydroxyestrone; 16a-Hydroxyestrone; 16α-Hydroxyestrone; 16-Hydroxyestrone; 16 alpha OHE; 16 a OHE; 16 Α ohe; 16alpha-Hydroxyestrone
数据库引用编号
18 个数据库交叉引用编号
- ChEBI: CHEBI:776
- KEGG: C05300
- PubChem: 115116
- HMDB: HMDB0000335
- Metlin: METLIN41829
- ChEMBL: CHEMBL1233720
- foodb: FDB021959
- chemspider: 103012
- CAS: 566-76-7
- PubChem: 7684
- LipidMAPS: LMST02010041
- PDB-CCD: J2Z
- 3DMET: B01840
- NIKKAJI: J130.683I
- RefMet: 16alpha-Hydroxyestrone
- KNApSAcK: 776
- LOTUS: LTS0258925
- wikidata: Q81988144
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
8 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(6)
- Estrone Metabolism:
2-Hydroxyestrone + S-Adenosylmethionine ⟶ 2-Methoxyestrone + S-Adenosylhomocysteine - Estrone Metabolism:
2-Hydroxyestrone + S-Adenosylmethionine ⟶ 2-Methoxyestrone + S-Adenosylhomocysteine - Estrone Metabolism:
2-Hydroxyestrone + S-Adenosylmethionine ⟶ 2-Methoxyestrone + S-Adenosylhomocysteine - Estrone Metabolism:
2-Hydroxyestrone + S-Adenosylmethionine ⟶ 2-Methoxyestrone + S-Adenosylhomocysteine - Estrone Metabolism:
2-Hydroxyestrone + S-Adenosylmethionine ⟶ 2-Methoxyestrone + S-Adenosylhomocysteine - Estrone Metabolism:
2-Hydroxyestrone + S-Adenosylmethionine ⟶ 2-Methoxyestrone + S-Adenosylhomocysteine
PharmGKB(0)
2 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
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2020 07; 201(?):105685. doi:
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Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2007 Feb; 16(2):256-62. doi:
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The Journal of steroid biochemistry and molecular biology.
2007 Feb; 103(2):158-62. doi:
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Molecular genetics and metabolism.
2006 Dec; 89(4):381-9. doi:
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Annals of the New York Academy of Sciences.
2006 Nov; 1089(?):538-47. doi:
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The American journal of medicine.
2006 Sep; 119(9 Suppl 1):S44-51. doi:
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Arthritis and rheumatism.
2006 Aug; 54(8):2481-7. doi:
10.1002/art.22005. [PMID: 16871545] - Edwin K Chan, Daniel W Sepkovic, Helen J Yoo Bowne, Guo Pei Yu, Stimson P Schantz. A hormonal association between estrogen metabolism and proliferative thyroid disease.
Otolaryngology--head and neck surgery : official journal of American Academy of Otolaryngology-Head and Neck Surgery.
2006 Jun; 134(6):893-900. doi:
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The Journal of nutrition.
2006 Jun; 136(6):1588-95. doi:
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International journal of gynecological cancer : official journal of the International Gynecological Cancer Society.
2006 Mar; 16(2):786-90. doi:
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European journal of clinical nutrition.
2006 Mar; 60(3):386-92. doi:
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The Journal of clinical endocrinology and metabolism.
2006 Mar; 91(3):1015-20. doi:
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Molecular genetics and metabolism.
2006 Feb; 87(2):135-46. doi:
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Epidemiology (Cambridge, Mass.).
2006 Jan; 17(1):80-8. doi:
10.1097/01.ede.0000190543.40801.75. [PMID: 16357599] - Anja Wellejus, Anja Olsen, Anne Tjonneland, Birthe L Thomsen, Kim Overvad, Steffen Loft. Urinary hydroxyestrogens and breast cancer risk among postmenopausal women: a prospective study.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2005 Sep; 14(9):2137-42. doi:
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Journal of the American College of Nutrition.
2005 Aug; 24(4):235-43. doi:
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Cancer causes & control : CCC.
2005 May; 16(4):455-61. doi:
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Applied microbiology and biotechnology.
2005 Apr; 67(1):106-12. doi:
10.1007/s00253-004-1693-4. [PMID: 15290133] - Jane Teas, Joan E Cunningham, Jay H Fowke, Daniela Nitcheva, C P Kanwat, R J Boulware, Daniel W Sepkovic, Thomas G Hurley, James R Hebert. Urinary estrogen metabolites, prostate specific antigen, and body mass index among African-American men in South Carolina.
Cancer detection and prevention.
2005; 29(6):494-500. doi:
10.1016/j.cdp.2005.08.004. [PMID: 16289388] - Valentina Paracchini, Paola Pedotti, Sara Raimondi, Seymour Garte, H Leon Bradlow, Daniel W Sepkovic, Emanuela Taioli. A common CYP1B1 polymorphism is associated with 2-OHE1/16-OHE1 urinary estrone ratio.
Clinical chemistry and laboratory medicine.
2005; 43(7):702-6. doi:
10.1515/cclm.2005.119. [PMID: 16207128] - Reina C Armamento-Villareal, Nicola Napoli, Thomas Klug, Roberto Civitelli. The oxidative metabolism of estrogen modulates response to ERT/HRT in postmenopausal women.
Bone.
2004 Sep; 35(3):682-8. doi:
10.1016/j.bone.2004.05.010. [PMID: 15336604] - Charles E Matthews, Jay H Fowke, Qi Dai, H Leon Bradlow, Fan Jin, Xiao-Ou Shu, Yu-Tang Gao, Christopher Longcope, James R Hebert, Wei Zheng. Physical activity, body size, and estrogen metabolism in women.
Cancer causes & control : CCC.
2004 Jun; 15(5):473-81. doi:
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International journal of environmental health research.
2004 Apr; 14(2):121-34. doi:
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International journal of clinical pharmacology and therapeutics.
2004 Mar; 42(3):160-4. doi:
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Lupus.
2004; 13(9):635-8. doi:
10.1191/0961203304lu1094oa. [PMID: 15485092] - Shelley S Tworoger, Jessica Chubak, Erin J Aiello, Cornelia M Ulrich, Charlotte Atkinson, John D Potter, Yutaka Yasui, Patricia L Stapleton, Johanna W Lampe, Federico M Farin, Frank Z Stanczyk, Anne McTiernan. Association of CYP17, CYP19, CYP1B1, and COMT polymorphisms with serum and urinary sex hormone concentrations in postmenopausal women.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2004 Jan; 13(1):94-101. doi:
10.1158/1055-9965.epi-03-0026. [PMID: 14744739] - Kathie M Dalessandri, Gary L Firestone, Mark D Fitch, H Leon Bradlow, Leonard F Bjeldanes. Pilot study: effect of 3,3'-diindolylmethane supplements on urinary hormone metabolites in postmenopausal women with a history of early-stage breast cancer.
Nutrition and cancer.
2004; 50(2):161-7. doi:
10.1207/s15327914nc5002_5. [PMID: 15623462] - A O Mueck, H Seeger, T H Lippert. [Estrogen-dependent neoplasia - what is the significance of estradiol metabolites].
Zentralblatt fur Gynakologie.
2003 Nov; 125(11):458-66. doi:
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Epidemiology (Cambridge, Mass.).
2003 Nov; 14(6):740-4. doi:
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The Journal of steroid biochemistry and molecular biology.
2003 Jul; 86(1):71-7. doi:
10.1016/s0960-0760(03)00259-0. [PMID: 12943746] - R B Alvarez-Vasquez, D Axelrod, K Frenkel, M C Newman, D W Sepkovic, H L Bradlow, B Zumoff. Influence of postmenopausal hormone replacement therapy on an estrogen metabolite biomarker of risk for breast cancer.
Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme.
2003 Jun; 35(6):358-61. doi:
10.1055/s-2003-41357. [PMID: 12920658] - H Jernström, T L Klug, D W Sepkovic, H L Bradlow, S A Narod. Predictors of the plasma ratio of 2-hydroxyestrone to 16alpha-hydroxyestrone among pre-menopausal, nulliparous women from four ethnic groups.
Carcinogenesis.
2003 May; 24(5):991-1005. doi:
10.1093/carcin/bgg047. [PMID: 12771045] - Diane S Thompson, Margaret A Kirshner, Thomas L Klug, Kari B Kastango, Bruce G Pollock. A preliminary study of the effect of fluoxetine treatment on the 2:16-alpha-hydroxyestrone ratio in young women.
Therapeutic drug monitoring.
2003 Feb; 25(1):125-8. doi:
10.1097/00007691-200302000-00021. [PMID: 12548158] - Seon Hwa Lee, Kyung Mee Kim, Byung Hwa Jung, Woung Youn Chung, Cheong Soo Park, Bong Chul Chung. Estrogens in female thyroid cancer: alteration of urinary profiles in pre- and post-operative cases.
Cancer letters.
2003 Jan; 189(1):27-32. doi:
10.1016/s0304-3835(02)00514-1. [PMID: 12445674] - Jay H Fowke, Dai Qi, H Leon Bradlow, Xiao Ou Shu, Yu Tang Gao, Jin Rong Cheng, Fan Jin, Wei Zheng. Urinary estrogen metabolites and breast cancer: differential pattern of risk found with pre- versus post-treatment collection.
Steroids.
2003 Jan; 68(1):65-72. doi:
10.1016/s0039-128x(02)00116-2. [PMID: 12475724] - Paola Muti, Kim Westerlind, Tiejian Wu, Thomas Grimaldi, John De Berry, Holger Schünemann, Jo L Freudenheim, Helyn Hill, Giuseppe Carruba, Leon Bradlow. Urinary estrogen metabolites and prostate cancer: a case-control study in the United States.
Cancer causes & control : CCC.
2002 Dec; 13(10):947-55. doi:
10.1023/a:1021986811425. [PMID: 12588091] - Sidika E Kasim-Karakas, Rogelio U Almario, Laura Gregory, Heather Todd, Rodney Wong, Bill L Lasley. Effects of prune consumption on the ratio of 2-hydroxyestrone to 16alpha-hydroxyestrone.
The American journal of clinical nutrition.
2002 Dec; 76(6):1422-7. doi:
10.1093/ajcn/76.6.1422. [PMID: 12450912] - Richard S Lord, Bradley Bongiovanni, J Alexander Bralley. Estrogen metabolism and the diet-cancer connection: rationale for assessing the ratio of urinary hydroxylated estrogen metabolites.
Alternative medicine review : a journal of clinical therapeutic.
2002 Apr; 7(2):112-29. doi:
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Breast cancer research and treatment.
2002 Mar; 72(2):139-43. doi:
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Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme.
2001 Dec; 33(12):744-7. doi:
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The Journal of endocrinology.
2001 Jul; 170(1):165-74. doi:
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Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2001 Jun; 10(6):627-34. doi:
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Journal of the National Cancer Institute.
2001 Apr; 93(7):554-5. doi:
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Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2001 Mar; 10(3):237-42. doi:
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Steroids.
2001 Jan; 66(1):59-62. doi:
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Gynecologic oncology.
2000 Aug; 78(2):123-9. doi:
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Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2000 Aug; 9(8):773-9. doi:
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Cancer research.
2000 Mar; 60(5):1299-305. doi:
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Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2000 Jan; 9(1):81-7. doi:
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Nutrition and cancer.
2000; 38(2):209-14. doi:
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