Equilin (BioDeep_00000003880)
Secondary id: BioDeep_00000637492
natural product
代谢物信息卡片
Estra-1,3,5(10),7-tetraen-17-one, 3-hydroxy-
化学式: C18H20O2 (268.1463)
中文名称: 马烯雌酮
谱图信息:
最多检出来源 Homo sapiens(lipidomics) 6.26%
分子结构信息
SMILES: C1C2[C@@]3([H])CC[C@]4(C)C(=O)CC[C@@]4([H])C3=CCC=2C=C(O)C=1
InChI: InChI=1S/C18H20O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3-5,10,14,16,19H,2,6-9H2,1H3/t14-,16+,18+/m1/s1
描述信息
D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones
Same as: D04041
同义名列表
数据库引用编号
33 个数据库交叉引用编号
- ChEBI: CHEBI:42309
- KEGG: C14392
- KEGGdrug: D04041
- PubChem: 223368
- PubChem: 3247
- Metlin: METLIN4012
- DrugBank: DB02187
- ChEMBL: CHEMBL323533
- LipidMAPS: LMST02010026
- MeSH: Equilin
- CAS: 474-86-2
- MoNA: Bruker_HCD_library000145
- MoNA: VF-NPL-QEHF027855
- MoNA: VF-NPL-QEHF027854
- MoNA: VF-NPL-QEHF027853
- MoNA: VF-NPL-QEHF027852
- MoNA: VF-NPL-QEHF027851
- MoNA: VF-NPL-QEHF027850
- MoNA: VF-NPL-QEHF027849
- MoNA: VF-NPL-QEHF027848
- MoNA: VF-NPL-QEHF027847
- MoNA: VF-NPL-QEHF027846
- MoNA: VF-NPL-QEHF027845
- MoNA: VF-NPL-QEHF027844
- MoNA: VF-NPL-QEHF027843
- MoNA: VF-NPL-QEHF027842
- MoNA: VF-NPL-QEHF027841
- PMhub: MS000012892
- PubChem: 17395392
- PDB-CCD: EQI
- NIKKAJI: J5.967F
- RefMet: ST 18:5;O2
- KNApSAcK: 42309
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)
0 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
- Jessica K Hartman, Tyler Beames, Bethany Parks, Daniel Doheny, Gina Song, Alina Efremenko, Miyoung Yoon, Briana Foley, Chad Deisenroth, Patrick D McMullen, Rebecca A Clewell. An in vitro approach for prioritization and evaluation of chemical effects on glucocorticoid receptor mediated adipogenesis.
Toxicology and applied pharmacology.
2018 09; 355(?):112-126. doi:
10.1016/j.taap.2018.05.016. [PMID: 29782964] - Wendy A Spencer, Manicka V Vadhanam, Jeyaprakash Jeyabalan, Ramesh C Gupta. Oxidative DNA damage following microsome/Cu(II)-mediated activation of the estrogens, 17β-estradiol, equilenin, and equilin: role of reactive oxygen species.
Chemical research in toxicology.
2012 Feb; 25(2):305-14. doi:
10.1021/tx200356v. [PMID: 22126130] - Stephen Cw Sze, Ho-Pan Cheung, Tzi-Bun Ng, Zhang-Jing Zhang, Kam-Lok Wong, Hei-Kiu Wong, Yong-Mei Hu, Christine Mn Yow, Yao Tong. Effects of Erxian decoction, a Chinese medicinal formulation, on serum lipid profile in a rat model of menopause.
Chinese medicine.
2011 Nov; 6(?):40. doi:
10.1186/1749-8546-6-40. [PMID: 22047073] - Rupinder K Bhamra, Marya B Margolis, James H Liu, Christopher H Hendy, Rand G Jenkins, Charles E DiLiberti. A randomized, multiple-dose parallel study to compare the pharmacokinetic parameters of synthetic conjugated estrogens, A, administered as oral tablet or vaginal cream.
Menopause (New York, N.Y.).
2011 Apr; 18(4):393-9. doi:
10.1097/gme.0b013e3181f7a2d6. [PMID: 21107298] - Joshua S Talboom, Elizabeth B Engler-Chiurazzi, Paul Whiteaker, Alain R Simard, Ronald Lukas, Jazmin I Acosta, Laszlo Prokai, Heather A Bimonte-Nelson. A component of Premarin(®) enhances multiple cognitive functions and influences nicotinic receptor expression.
Hormones and behavior.
2010 Nov; 58(5):917-28. doi:
10.1016/j.yhbeh.2010.09.002. [PMID: 20849857] - Rupinder Bhamra, Uwe Kaercher, Christine M Oleary. Pharmacokinetics of a modified-release estrogen tablet.
The Journal of reproductive medicine.
2010 Sep; 55(9-10):404-10. doi:
. [PMID: 21043366] - Paweł K Zarzycki, Elzbieta Włodarczyk, Michał J Baran. Determination of endocrine disrupting compounds using temperature-dependent inclusion chromatography: II. Fast screening of free steroids and related low-molecular-mass compounds fraction in the environmental samples derived from surface waters, treated and untreated sewage waters as well as activated sludge material.
Journal of chromatography. A.
2009 Oct; 1216(44):7612-22. doi:
10.1016/j.chroma.2009.03.066. [PMID: 19356767] - Philip Mayer, Susanna Tse, Mary Sendi, Dale Bourg, Dennis Morrison. Steady-state pharmacokinetics of conjugated equine estrogens in healthy, postmenopausal women.
The Journal of reproductive medicine.
2008 Feb; 53(2):97-101. doi:
. [PMID: 18357800] - Liqin Zhao, Roberta Diaz Brinton. Select estrogens within the complex formulation of conjugated equine estrogens (Premarin) are protective against neurodegenerative insults: implications for a composition of estrogen therapy to promote neuronal function and prevent Alzheimer's disease.
BMC neuroscience.
2006 Mar; 7(?):24. doi:
10.1186/1471-2202-7-24. [PMID: 16533397] - Bhagu R Bhavnani, Mauricio Berco, Julie Binkley. Equine estrogens differentially prevent neuronal cell death induced by glutamate.
Journal of the Society for Gynecologic Investigation.
2003 Jul; 10(5):302-8. doi:
10.1016/s1071-5576(03)00087-x. [PMID: 12853093] - Bhagu R Bhavnani. Estrogens and menopause: pharmacology of conjugated equine estrogens and their potential role in the prevention of neurodegenerative diseases such as Alzheimer's.
The Journal of steroid biochemistry and molecular biology.
2003 Jun; 85(2-5):473-82. doi:
10.1016/s0960-0760(03)00220-6. [PMID: 12943738] - R E Stevens, R Roy, K V Phelps. Evaluation of single- and multiple-dose pharmacokinetics of synthetic conjugated estrogens, A (Cenestin) tablets: a slow-release estrogen replacement product.
Journal of clinical pharmacology.
2002 Mar; 42(3):332-41. doi:
10.1177/00912700222011256. [PMID: 11865971] - Bhagu R Bhavnani, Anthony Cecutti, Alan Gerulath. Pharmacokinetics of 17 beta-dihydroequilin sulfate in normal postmenopausal women under steady state conditions.
Journal of the Society for Gynecologic Investigation.
2002 Mar; 9(2):102-10. doi:
10.1016/s1071-5576(01)00154-x. [PMID: 12398033] - Taiko Oda, Noriko Ikeda, Shoko Nakashima, Yoshihiro Sato. Cytotoxicity of estradiol, equilin, equilenin, and their derivatives on Chinese hamster V79 cells.
Drug and chemical toxicology.
2002 Feb; 25(1):75-82. doi:
10.1081/dct-100108473. [PMID: 11850971] - Teruo Murakami, Takeshi Fukuda, Ryoko Yumoto, Junya Nagai, Taiju Kuramoto, Mikihisa Takano. Interaction of endogenous compounds in human and rat urine with P-glycoprotein.
Drug metabolism and pharmacokinetics.
2002; 17(3):245-52. doi:
10.2133/dmpk.17.245. [PMID: 15618676] - B R Bhavnani, A Cecutti, A Gerulath, A C Woolever, M Berco. Comparison of the antioxidant effects of equine estrogens, red wine components, vitamin E, and probucol on low-density lipoprotein oxidation in postmenopausal women.
Menopause (New York, N.Y.).
2001 Nov; 8(6):408-19. doi:
10.1097/00042192-200111000-00005. [PMID: 11723413] - S B Lima, I T Verreschi, L M Ribeiro Neto. Reversed-phase liquid chromatographic method for estrogen determination in equine biological samples.
Journal of chromatographic science.
2001 Sep; 39(9):385-7. doi:
10.1093/chromsci/39.9.385. [PMID: 11565948] - M Berco, B R Bhavnani. Differential neuroprotective effects of equine estrogens against oxidized low density lipoprotein-induced neuronal cell death.
Journal of the Society for Gynecologic Investigation.
2001 Jul; 8(4):245-54. doi:
10.1016/s1071-5576(01)00111-3. [PMID: 11525901] - M A Bacigalupo, A Ius, P Simoni, F Piazza, A Roda, K D Setchell. Analytical performance of luminescent immunoassays of different format for serum daidzein analysis.
Fresenius' journal of analytical chemistry.
2001 May; 370(1):82-7. doi:
10.1007/s002160100717. [PMID: 11393242] - B R Bhavnani, J A Nisker, J Martin, F Aletebi, L Watson, J K Milne. Comparison of pharmacokinetics of a conjugated equine estrogen preparation (premarin) and a synthetic mixture of estrogens (C.E.S.) in postmenopausal women.
Journal of the Society for Gynecologic Investigation.
2000 May; 7(3):175-83. doi:
10.1016/s1071-5576(00)00049-6. [PMID: 10865186] - R Gatti, M Franchina, M G Gioia, V Cavrini. HPLC-fluorescence determination of equilin and equilenin in postmenopausal women's urine.
Biomedical chromatography : BMC.
2000 Apr; 14(2):82-8. doi:
10.1002/(sici)1099-0801(200004)14:2<82::aid-bmc930>3.0.co;2-a. [PMID: 10694700] - E Barrett-Connor, R Young, M Notelovitz, J Sullivan, B Wiita, H M Yang, J Nolan. A two-year, double-blind comparison of estrogen-androgen and conjugated estrogens in surgically menopausal women. Effects on bone mineral density, symptoms and lipid profiles.
The Journal of reproductive medicine.
1999 Dec; 44(12):1012-20. doi:
. [PMID: 10649811] - E Arteaga, P Villaseca. Pharmacokinetic comparison between Conpremin (Premarin) and a generic preparation of conjugated estrogens.
Climacteric : the journal of the International Menopause Society.
1998 Dec; 1(4):284-9. doi:
10.3109/13697139809085556. [PMID: 11907935] - A Wakatsuki, N Ikenoue, Y Sagara. Effects of estrogen on susceptibility to oxidation of low-density and high-density lipoprotein in postmenopausal women.
Maturitas.
1998 Jan; 28(3):229-34. doi:
10.1016/s0378-5122(97)00072-8. [PMID: 9571598] - M D Hornstein, E S Surrey, G W Weisberg, L A Casino. Leuprolide acetate depot and hormonal add-back in endometriosis: a 12-month study. Lupron Add-Back Study Group.
Obstetrics and gynecology.
1998 Jan; 91(1):16-24. doi:
10.1016/s0029-7844(97)00620-0. [PMID: 9464714] - R D Brinton, P Proffitt, J Tran, R Luu. Equilin, a principal component of the estrogen replacement therapy premarin, increases the growth of cortical neurons via an NMDA receptor-dependent mechanism.
Experimental neurology.
1997 Oct; 147(2):211-20. doi:
10.1006/exnr.1997.6619. [PMID: 9344546] - J G Wilcox, F Z Stanczyk, R S Morris, E Gentzschein, R A Lobo. Biologic effects of 17 alpha-dihydroequilin sulfate.
Fertility and sterility.
1996 Nov; 66(5):748-52. doi:
10.1016/s0015-0282(16)58629-4. [PMID: 8893678] - S A Washburn, E K Honoré, J M Cline, M Helman, J D Wagner, S J Adelman, T B Clarkson. Effects of 17 alpha-dihydroequilenin sulfate on atherosclerotic male and female rhesus monkeys.
American journal of obstetrics and gynecology.
1996 Aug; 175(2):341-9; discussion 349. doi:
10.1016/s0002-9378(96)70144-8. [PMID: 8765251] - C J Kim, Y K Min, W S Ryu, J W Kwak, U H Ryoo. Effect of hormone replacement therapy on lipoprotein(a) and lipid levels in postmenopausal women. Influence of various progestogens and duration of therapy.
Archives of internal medicine.
1996 Aug; 156(15):1693-700. doi:
". [PMID: 8694668] - M Tang, W Abplanalp, S Ayres, M T Subbiah. Superior and distinct antioxidant effects of selected estrogen metabolites on lipid peroxidation.
Metabolism: clinical and experimental.
1996 Apr; 45(4):411-4. doi:
10.1016/s0026-0495(96)90212-7. [PMID: 8609824] - S Ikegawa, M Itoh, N Murao, H Kijima, M Suzuki, T Fujiyama, J Goto. Immunoaffinity extraction for liquid chromatographic determination of equilin and its metabolites in plasma.
Biomedical chromatography : BMC.
1996 Mar; 10(2):73-7. doi:
10.1002/(sici)1099-0801(199603)10:2<73::aid-bmc561>3.0.co;2-5. [PMID: 8924730] - A Chandrasekaran, M Osman, S J Adelman, J Warsheski, J Scatina, S F Sisenwine. Determination of 17 alpha-dihydroequilenin in rat, rabbit and monkey plasma by high-performance liquid chromatography with fluorimetric detection.
Journal of chromatography. B, Biomedical applications.
1996 Feb; 676(1):69-75. doi:
10.1016/0378-4347(95)00407-6. [PMID: 8852046] - A Chandrasekaran, M Osman, J A Scatina, S F Sisenwine. Metabolism of equilin sulfate in the dog.
The Journal of steroid biochemistry and molecular biology.
1995 Nov; 55(2):271-8. doi:
10.1016/0960-0760(95)00161-r. [PMID: 7495708] - Sulistiyani, S J Adelman, A Chandrasekaran, J Jayo, R W St Clair. Effect of 17 alpha-dihydroequilin sulfate, a conjugated equine estrogen, and ethynylestradiol on atherosclerosis in cholesterol-fed rabbits.
Arteriosclerosis, thrombosis, and vascular biology.
1995 Jul; 15(7):837-46. doi:
10.1161/01.atv.15.7.837. [PMID: 7600114] - B R Bhavnani, A Cecutti, D Wallace. Metabolism of [3H] 17 beta-dihydroequilin and [3H] 17 beta-dihydroequilin sulfate in normal postmenopausal women.
Steroids.
1994 Jun; 59(6):389-94. doi:
10.1016/0039-128x(94)90007-8. [PMID: 7940618] - B R Bhavnani, A Cecutti. Pharmacokinetics of 17 beta-dihydroequilin sulfate and 17 beta-dihydroequilin in normal postmenopausal women.
The Journal of clinical endocrinology and metabolism.
1994 Jan; 78(1):197-204. doi:
10.1210/jcem.78.1.8288704. [PMID: 8288704] - B R Bhavnani, A Cecutti. Metabolic clearance rate of equilin sulfate and its conversion to plasma equilin, conjugated and unconjugated equilenin, 17 beta-dihydroequilin, and 17 beta-dihydroequilenin in normal postmenopausal women and men under steady state conditions.
The Journal of clinical endocrinology and metabolism.
1993 Nov; 77(5):1269-74. doi:
10.1210/jcem.77.5.8077320. [PMID: 8077320] - M T Subbiah, B Kessel, M Agrawal, R Rajan, W Abplanalp, Z Rymaszewski. Antioxidant potential of specific estrogens on lipid peroxidation.
The Journal of clinical endocrinology and metabolism.
1993 Oct; 77(4):1095-7. doi:
10.1210/jcem.77.4.8408459. [PMID: 8408459] - S A Washburn, M R Adams, T B Clarkson, S J Adelman. A conjugated equine estrogen with differential effects on uterine weight and plasma cholesterol in the rat.
American journal of obstetrics and gynecology.
1993 Aug; 169(2 Pt 1):251-4; discussion 254. doi:
10.1016/0002-9378(93)90072-q. [PMID: 8395768] - G H Degen. Interaction of phytoestrogens and other environmental estrogens with prostaglandin synthase in vitro.
Journal of steroid biochemistry.
1990 Mar; 35(3-4):473-9. doi:
10.1016/0022-4731(90)90256-r. [PMID: 2139153] - B R Bhavnani, C A Woolever, D Wallace, C C Pan. Metabolism of [3H]equilin-[35S]sulfate and [3H]equilin sulfate after oral and intravenous administration in normal postmenopausal women and men.
The Journal of clinical endocrinology and metabolism.
1989 Apr; 68(4):757-65. doi:
10.1210/jcem-68-4-757. [PMID: 2921309] - R A Lobo, H N Nguyen, P Eggena, P F Brenner. Biologic effects of equilin sulfate in postmenopausal women.
Fertility and sterility.
1988 Feb; 49(2):234-8. doi:
10.1016/s0015-0282(16)59708-8. [PMID: 3338581] - C C Pan, C A Woolever, B R Bhavnani. Transport of equine estrogens: binding of conjugated and unconjugated equine estrogens with human serum proteins.
The Journal of clinical endocrinology and metabolism.
1985 Sep; 61(3):499-507. doi:
10.1210/jcem-61-3-499. [PMID: 4040531] - B R Bhavnani, C A Woolever, H Benoit, T Wong. Pharmacokinetics of equilin and equilin sulfate in normal postmenopausal women and men.
The Journal of clinical endocrinology and metabolism.
1983 May; 56(5):1048-56. doi:
10.1210/jcem-56-5-1048. [PMID: 6300173] - L Siekmann, A Siekmann, H Breuer, L Dehennin. Measurement by isotope dilution mass spectrometry of equiline and oestrone in serum of women taking tablets of equine oestrogens.
Biomedical mass spectrometry.
1983 Mar; 10(3):168-74. doi:
10.1002/bms.1200100311. [PMID: 6303469] - B R Bhavnani, C A Woolever. The metabolism of equilin in normal men.
Journal of steroid biochemistry.
1982 Aug; 17(2):217-23. doi:
10.1016/0022-4731(82)90125-x. [PMID: 7109607] - B R Bhavnani, I R Sarda, C A Woolever. Radioimmunoassay of plasma equilin and estrone in postmenopausal women after the administration of premarin.
The Journal of clinical endocrinology and metabolism.
1981 Apr; 52(4):741-7. doi:
10.1210/jcem-52-4-741. [PMID: 6259193] - B R Bhavnani, C A Woolever. In vivo metabolism of [3H]equilin in the pregnant mare.
Endocrinology.
1981 Jan; 108(1):232-8. doi:
10.1210/endo-108-1-232. [PMID: 7460819] - P N Rao, R H Purdy, P H Moore, J W Goldzieher. Synthesis of new steroid haptens for radioimmunoassay--VI. 3-O-Carboxymethyl ether derivatives of equine estrogens. Highly specific antisera for measurement of equilin and 17 alpha-dihydroequilin in plasma.
Journal of steroid biochemistry.
1980 Nov; 13(11):1291-8. doi:
10.1016/0022-4731(80)90089-8. [PMID: 6256584] - M R Morgan, P G Whittaker, B P Fuller, P D Dean. A radioimmunoassay for equilin in post-menopausal plasma: plasma levels of equilin determined after oral administration of conjugated equine oestrogens (premarin).
Journal of steroid biochemistry.
1980 May; 13(5):551-5. doi:
10.1016/0022-4731(80)90212-5. [PMID: 6248689] - C A Woolever, B R Bhavnani. Serum equilin and conjugated equine oestrogens.
Lancet (London, England).
1980 Mar; 1(8167):547-8. doi:
10.1016/s0140-6736(80)92808-1. [PMID: 6102273] - P G Whittaker, M R Morgan, P D Dean, E H Cameron, T Lind. Serum equilin, oestrone, and oestradiol levels in postmenopausal women receiving conjugated equine oestrogens ('Premarin').
Lancet (London, England).
1980 Jan; 1(8158):14-6. doi:
10.1016/s0140-6736(80)90552-8. [PMID: 6101354] - M R Morgan, P G Whittaker, P D Dean, E A Lenton, L Sexton, I D Cooke. Plasma equilin concentrations in an oophorectomized woman following ingestion of conjugated equine oestrogens (Premarin).
European journal of clinical investigation.
1979 Dec; 9(6):473-4. doi:
10.1111/j.1365-2362.1979.tb00915.x. [PMID: 231519] - L Giuliani, G Carmignani, E Belgrano, P Puppo. Transcatheter arterial embolization in urological tumors: the use of isobutyl-2-cyanoacrylate.
The Journal of urology.
1979 May; 121(5):630-4. doi:
10.1016/s0022-5347(17)56913-x. [PMID: 439260] - T A Rance, B K Park. The measurement of oestrone, equilin and dehydroepiandrosterone in the peripheral plasma of pregnant pony mares by radioimmunoassay.
Journal of steroid biochemistry.
1978 Nov; 9(11):1065-9. doi:
10.1016/0022-4731(78)90033-x. [PMID: 154595] - M Gold, G Mathew. The use of equilin as an internal standard to quantitate estriol in pregnancy urine.
Clinical biochemistry.
1977 Oct; 10(5):191-2. doi:
10.1016/s0009-9120(77)92900-9. [PMID: 912858] - R F Parkes, D J Blackmore, T A Rance, B K Park, P D Dean. Plasma concentrations of equilin and oestrone in the assessment of fetoplacental function in the mare.
The Veterinary record.
1977 Jun; 100(24):511-2. doi:
10.1136/vr.100.24.511. [PMID: 878268] - B K Park, T A Rance, P D Dean. A radioimmunoassay for equilin in equine pregnancy plasma.
FEBS letters.
1976 Nov; 72(1):18-20. doi:
10.1016/0014-5793(76)80888-5. [PMID: 992084] - J E Cox. Oestrone and equilin in the plasma of the pregnant mare.
Journal of reproduction and fertility. Supplement.
1975 Oct; ?(23):463-8. doi:
. [PMID: 1060825] - J I Raeside, R M Liptrap. Patterns of urinary oestrogen excretion in individual pregnant mares.
Journal of reproduction and fertility. Supplement.
1975 Oct; ?(23):649-75. doi:
NULL. [PMID: 1060860] - T M Nett, D W Holtan, V L Estergreen. Oestrogens, LH, PMSG, and prolactin in serum of pregnant mares.
Journal of reproduction and fertility. Supplement.
1975 Oct; ?(23):457-62. doi:
. [PMID: 1060824] - P Goddard, F Fernandez, B West, M J Hill, P Barnes. The nuclear dehydrogenation of steroids by intestinal bacteria.
Journal of medical microbiology.
1975 Aug; 8(3):429-35. doi:
10.1099/00222615-8-3-429. [PMID: 1177289] - W L GLEN, R BARBER, H M MCCONKEY, G A GRANT. Isolation of beta-dihydroequilin and alpha-dihydroequilenin from the urine of pregnant mares.
Nature.
1956 Apr; 177(4512):753. doi:
10.1038/177753a0. [PMID: 13321954]
