ent-Estradiol

ent-Estradiol (ent-E2), or 1-estradiol (1-E2), is an estrogen and the 1-enantiomorph of estradiol.[1][2][3] It is a so-called "short-acting" or "impeded" estrogen, similarly to estriol, 17α-estradiol, and dimethylstilbestrol.[1][2][3]

Ent-Estradiol
Clinical data
Other namesent-E2; 1-Estradiol; 1-E2
Drug classEstrogen
Identifiers
IUPAC name
  • (8S,9R,13R,14R,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol
CAS Number
PubChem CID
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H24O2
Molar mass272.388 g·mol−1
3D model (JSmol)
SMILES
  • C[C@@]12CC[C@@H]3[C@@H]([C@H]1CC[C@H]2O)CCC4=C3C=CC(=C4)O
InChI
  • InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17+,18+/m0/s1
  • Key:VOXZDWNPVJITMN-QXDIGNSFSA-N

References
  1. Edgren RA, Jones RC (September 1969). "An anti-estradiol effect of ent-estradiol-17beta (1-estradiol)". Steroids. 14 (3): 335–41. doi:10.1016/0039-128x(69)90021-x. PMID 5821989.
  2. Terenius L, Ljungkvist I (1972). "Aspects on the mode of action of antiestrogens and antiprogestogens". Gynecol Invest. 3 (1): 96–107. doi:10.1159/000301746. PMID 4347201.
  3. Terenius L (June 1971). "The Allen-Doisy test for estrogens reinvestigated". Steroids. 17 (6): 653–61. doi:10.1016/0039-128x(71)90081-x. PMID 5104534.



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