Structure via PubChem · Public domain (PubChem)
2-hydroxyestradiol
Sign in to saveAlso known as 2-OH-E2, 2-OH-estradiol, (17beta)-estra-1,3,5(10)-triene-2,3,17-triol, 2-Hydroxyestradiol-17beta, Estra-1,3,5(10)-triene-2,3,17b-triol, Estra-1,3,5(10)-triene-2,3,17-triol (ACD/Name 4.0), Estra-1,3,5(10)-triene-2,3,17-beta-triol, (17b)-Estra-1,3, 5(10)-triene-2,3,17-triol
2-Hydroxyestradiol (2-OHE2), also known as estra-1,3,5(10)-triene-2,3,17β-triol, is an endogenous steroid, catechol estrogen, and metabolite of estradiol, as well as a positional isomer of estriol.
Chemical data
- Formula
- C18H24O3
- Molecular weight
- 288.4 g/mol
- IUPAC name
- (8R,9S,13S,14S,17S)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-2,3,17-triol
- SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=CC(=C(C=C34)O)O
- InChIKey
- DILDHNKDVHLEQB-XSSYPUMDSA-N
- XLogP
- 3.7
- Polar surface area
- 60.7 Ų
- H-bond donors
- 3
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 288.173
Show 4 more facts
- canonical SMILES
- CC12CCC3C(C1CCC2O)CCC4=CC(=C(C=C34)O)O
- isomeric SMILES
- C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=CC(=C(C=C34)O)O
- chemical formula
- C₁₈H₂₄O₃
- found in taxon
- Homo sapiens
via Wikidata · CC0
~6 min read
Encyclopedic overview
9 sectionsContents
- Biosynthesis
- Biological activity
- Estrogenic activity
- Catecholaminergic activity
- Genotoxicity
- Production of 2-methoxyestradiol
- Antioxidant activity
- History
- References
2-Hydroxyestradiol (2-OHE2), also known as estra-1,3,5(10)-triene-2,3,17β-triol, is an endogenous steroid, catechol estrogen, and metabolite of estradiol, as well as a positional isomer of estriol.
==Biosynthesis== Transformation of estradiol to 2-hydroxyestradiol is a major metabolic pathway of estradiol in the liver. CYP1A2 and CYP3A4 are the major enzymes catalyzing the 2-hydroxylation of estradiol. Conversion of estradiol into 2-hydroxyestradiol has also been detected in the uterus, breast, kidney, brain, and pituitary gland, as well as the placenta, and may similarly be mediated by cytochrome P450 enzymes. Although estradiol is extensively converted into 2-hydroxyestradiol, circulating levels of 2-hydroxyestradiol and levels of 2-hydroxyestradiol in various tissues are very low. This may be due to rapid conjugation (O-methylation, glucuronidation, sulfonation) of 2-hydroxyestradiol followed by urinary excretion.
Excerpted from Wikipedia’s “2-hydroxyestradiol” article, available under the CC BY-SA 4.0 licence.