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4-甲氧基雌三醇

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4-甲氧基雌三醇
IUPAC名
(8R,9S,13S,14S,16R,17R)-4-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,16,17-triol
別名 4-MeO-E3; 4-Methoxyestra-1,3,5(10)-triene-3,16α,17β-triol
識別
CAS號 101534-28-5  checkY
PubChem 9901559
ChemSpider 8077213
SMILES
 
  • C[C@]12CC[C@H]3[C@H]([C@@H]1C[C@H]([C@@H]2O)O)CCC4=C3C=CC(=C4OC)O
InChI
 
  • 1S/C19H26O4/c1-19-8-7-11-10-5-6-15(20)17(23-2)13(10)4-3-12(11)14(19)9-16(21)18(19)22/h5-6,11-12,14,16,18,20-22H,3-4,7-9H2,1-2H3/t11-,12-,14+,16-,18+,19+/m1/s1
InChIKey MTZUPVFOGAXGJG-JUVWIQMMSA-N
性質
化學式 C19H26O4
摩爾質量 318.41 g·mol−1
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

4-甲氧基雌三醇(英語:4-Methoxyestriol,縮寫4-ME3)是一種內源性的雌激素雌三醇代謝產物[1][2][3][4]。4-ME3可看作是4-羥基雌三醇的4-甲基[1][2][3]。4-甲氧基雌三醇對雌激素受體的親和力非常低[4]其對ERαERβ的相對親和力(RBAs)只有雌二醇的約1%[4],相比之下,雌三醇對ERα和ERβ兩者的RBAs為11%和35%[4]

參考資料

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  1. ^ 1.0 1.1 Gerhardt K, Ludwig-Köhn H, Henning HV, Remberg G, Zeeck A. Identification of oestrogen metabolites in human urine by capillary gas chromatography and mass spectrometry. Biomed. Environ. Mass Spectrom. February 1989, 18 (2): 87–95. PMID 2706375. doi:10.1002/bms.1200180202. 
  2. ^ 2.0 2.1 Gaikwad NW. Ultra performance liquid chromatography-tandem mass spectrometry method for profiling of steroid metabolome in human tissue. Anal. Chem. May 2013, 85 (10): 4951–60. PMID 23597399. doi:10.1021/ac400016e. 
  3. ^ 3.0 3.1 Fujii Y, Teranishi M, Nakada K, Yamazaki M, Kishida S, Miyabo S. Radioimmunoassay for the determination of 2-methoxyestriol concentration in plasma of pregnant women. Chem. Pharm. Bull. February 1992, 40 (2): 410–3. PMID 1606638. doi:10.1248/cpb.40.410可免費查閱. 
  4. ^ 4.0 4.1 4.2 4.3 Zhu BT, Han GZ, Shim JY, Wen Y, Jiang XR. Quantitative structure-activity relationship of various endogenous estrogen metabolites for human estrogen receptor alpha and beta subtypes: Insights into the structural determinants favoring a differential subtype binding. Endocrinology. September 2006, 147 (9): 4132–50. PMID 16728493. doi:10.1210/en.2006-0113可免費查閱. 

外部連結

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