17β-estradiol   Click here for help

GtoPdb Ligand ID: 1013

Abbreviated name: E2
Synonyms: estrogen | oestrodiol | oestrogen
Approved drug PDB Ligand
17β-estradiol is an approved drug (FDA (1954, prior history unavailable))
Compound class: Metabolite
Comment: 17β-estradiol is the predominant form of circulating estrogen and is the endogenous agonist of the estrogen receptor α. In pre-menopausal women 17β-estradiol is mainly produced by the ovaries and placenta and is produced by adipose tissue in men and postmenopausal women.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 2
Rotatable bonds 0
Topological polar surface area 40.46
Molecular weight 272.18
XLogP 4.23
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Oc1ccc2c(c1)CCC1C2CCC2(C1CCC2O)C
Isomeric SMILES Oc1ccc2c(c1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C
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+/m1/s1
InChI Key VOXZDWNPVJITMN-ZBRFXRBCSA-N
References
1. Jones SA, Moore LB, Shenk JL, Wisely GB, Hamilton GA, McKee DD, Tomkinson NC, LeCluyse EL, Lambert MH, Willson TM, Kliewer SA, Moore JT. (2000)
The pregnane X receptor: a promiscuous xenobiotic receptor that has diverged during evolution.
Mol Endocrinol, 14 (1): 27-39. [PMID:10628745]
2. Kuiper GG, Carlsson B, Grandien K, Enmark E, Häggblad J, Nilsson S, Gustafsson JA. (1997)
Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta.
Endocrinology, 138 (3): 863-70. [PMID:9048584]
3. Nielsen CU, Pedersen M, Müller S, Kæstel T, Bjerg M, Ulaganathan N, Nielsen S, Carlsen KL, Nøhr MK, Holm R. (2021)
Inhibitory Effects of 17-α-Ethinyl-Estradiol and 17-β-Estradiol on Transport Via the Intestinal Proton-Coupled Amino Acid Transporter (PAT1) Investigated In Vitro and In Vivo.
J Pharm Sci, 110 (1): 354-364. [PMID:32835702]
4. Revankar CM, Cimino DF, Sklar LA, Arterburn JB, Prossnitz ER. (2005)
A transmembrane intracellular estrogen receptor mediates rapid cell signaling.
Science, 307 (5715): 1625-30. [PMID:15705806]
5. Thomas P, Pang Y, Filardo EJ, Dong J. (2005)
Identity of an estrogen membrane receptor coupled to a G protein in human breast cancer cells.
Endocrinology, 146 (2): 624-32. [PMID:15539556]
6. Valverde MA, Rojas P, Amigo J, Cosmelli D, Orio P, Bahamonde MI, Mann GE, Vergara C, Latorre R. (1999)
Acute activation of Maxi-K channels (hSlo) by estradiol binding to the beta subunit.
Science, 285 (5435): 1929-31. [PMID:10489376]